In The Fine Art of Small Talk, Debra Fine explains the benefits of mastering small talk and teaches you to confidently converse with strangers. According to Fine, the opportunity for casual conversations crops up many times each day—with neighbors, kids, and coworkers, and at social events, business lunches, and even the local supermarket. When we avoid small talk, she explains, we minimize the number of deep conversations we get to have in these settings. Furthermore, Fine says, we risk giving the impression that we’re cold, disinterested, or rude.
(Shortform note: Fine's assertion that avoiding small talk can appear rude may seem a little unfair if you're shy: Shy people avoid conversation not because they're rude, but because they feel anxious or awkward. They want to connect, but they don't know how. Unfortunately, though, others may not realize that shyness fuels this behavior: They might just assume that you're rude or aloof. This is why it's so important for shy people who want to connect to get out of their comfort zones and try to overcome their shyness.)
In this guide, we’ll first examine what Fine considers to be a helpful mindset in learning to master small talk. Then, we’ll discuss Fine’s step-by-step guide to conversation, from opening to exit. Finally, we’ll explore Fine’s more detailed tips regarding advance preparation for conversation and conversational conduct.
Clearly, small talk is a valuable tool—but what if it doesn’t come naturally to you? The good news, according to Fine, is that anyone can learn to be a good conversationalist: It’s just a matter of practice and mindset.
(Shortform note: When you want to learn or improve, your mindset—as Fine notes—affects how successful you can be. In particular, you’ll want to adopt a “growth mindset,” rather than a “fixed mindset.” When you hold a growth mindset, you remain open to improvement: You accept the belief that there’s no limit to how far learning and practice will take you. In contrast, those with a fixed mindset believe they’re limited to the traits, intelligence, and potential they were born with.)
According to Fine, taking the following principles to heart as you practice small talk will give you the best chance of improving:
1. If you want something, Fine says, go get it. If your goal is to meet new people, don’t just stand around alone or talk to people you already know. Instead, actively approach strangers.
(Shortform note: Why is being proactive so important? Stephen Covey, author of The 7 Habits of Highly Effective People, explains it’s because initiative is key to adopting new behaviors—it’s how we exert control over our circumstances. Covey might say that if you’re bad at small talk, it’s time to stop just letting small talk happen to you. Instead, accept that you’re having trouble, take responsibility for improving, and actively make an effort to change.)
2. According to Fine, it’s your job to start the conversation. The second most common fear in America is of starting conversations, particularly with strangers. Because this fear is so common, you’re unlikely to face rejection if you initiate conversation—in fact, your conversational partner is likely to be relieved that you made the effort.
(Shortform note: Contrary to Fine’s claim, America’s most common fears change year-to-year based on the circumstances we’re dealing with—a fear of conversing with strangers doesn’t usually make the top 10. At the time of The Fine Art’s publication, for example, it was often claimed that Americans’ number one fear was of public speaking, though fears of terrorist attacks sometimes polled higher. In 2021, the most common fears were of political corruption, the death of a loved one, or of a loved one contracting the coronavirus.)
3. It’s as much your job to carry the conversation as it is your partner’s, Fine notes. When you leave the hard work of maintaining conversation to someone else, you selfishly put your comfort ahead of theirs. Conversation is a two-player game, and you need to participate equally.
(Shortform note: Fine’s point that you have to learn to carry your weight echoes a common complaint that she implies, but doesn’t openly state: that too many people refuse to hold up their end of a conversation. If you want to be a better conversationalist, you must be willing to take charge and set the direction. Aim to do so multiple times in every encounter, to ensure you’re practicing this skill.)
Now that you understand it’s your responsibility to participate actively in conversations, we’ll delve into Fine’s four-step guide to a successful conversation.
Before you can start a conversation, you have to find someone to have that conversation with. When choosing someone to talk to, Fine recommends the following two-step process:
1. Scan the room and find someone who’s on their own, who’s not engaged in a conversation or an activity, and who makes eye contact with you.
(Shortform note: There are far more signals that someone doesn’t want to talk than Fine lists: Leave people alone if they’re wearing headphones, reading, crossing their arms or showing other “closed” body language, or if they turn away from you when you look at them.)
2. When you make eye contact, smile at the person. Fine explains that this shows the other party you’re interested in them and immediately establishes a rapport. When you smile at someone, their natural response is to smile back; right off the bat, the two of you share a positive feeling.
(Shortform note: Fine’s principle assumes that the other person will smile back; but what if they don’t? Is trying to connect then a lost cause? Probably: Research indicates that a genuine smile communicates a desire to engage cooperatively and altruistically. We can reverse this to imply that someone who doesn’t genuinely smile back doesn’t want to cooperate and converse with you.)
Once you’ve chosen a conversational partner and established rapport through a smile, walk up to them, Fine suggests, make eye contact, smile again and shake their hand.
(Shortform note: Fine suggests handshaking because, in Western society, it’s the polite thing to do—but you don’t have to do it. If you don’t want to shake hands, the Harvard Business Review recommends you communicate warmth, friendliness, and respect in another way, such as by offering a small bow.)
Say, “Hi. My name is…” Then, stay focused as the other person returns the introduction. Remember their name and use it immediately: For instance, say “Nice to meet you, Albert!” If you miss a person’s name, Fine recommends asking them to repeat it. Remember that everyone has the right to be called by their name, she notes, and that those with difficult names will appreciate it.
(Shortform note: It’s not just people with difficult names who’ll appreciate your efforts: According to Dale Carnegie, everyone is thrilled when someone learns and uses their name. Carnegie argues that a person’s name is the most important word in any language to them—saying it is a subtle and welcome compliment. In contrast, forgetting a name or getting it wrong suggests you didn’t care enough to get it right. Use a person’s name often, he says, and respect it.)
We’ve explored how to find a conversational partner and introduce yourself to them. Now that we’re ready to have a conversation, let’s explore how to start one.
The first step in starting a conversation, Fine explains, is to break the ice. According to Fine, it doesn’t matter much what you say as an opener; in theory, you could say anything. What matters is that you initiate the conversation and show genuine interest in the other person’s answer. Her recommendation, if you’re having trouble, is to open with a statement that uses the context of the situation, event, or venue, and then ask them a related question.
If you’re afraid to talk to someone because you fear you’ll have nothing in common, Fine suggests you keep in mind that humans are more alike than they are different. If you give other people a chance, she says, you’ll find you can connect with almost anyone.
(Shortform note: You may feel doubtful that Fine is correct here; surely, considering the diverse range of cultures and life practices that exist across the world (and even within countries), it’s optimistic to say we can connect with almost anyone? However, according to research, Fine is correct: The human experience, broadly speaking, is less diverse than it seems. In a study spanning 62 countries around the world, researchers found that our daily experiences are largely universal. For instance, we all care about our friends, want to love and be loved, and enjoy laughing, companionship, and cooperation.)
Easy Ways to Start Talking
Sometimes, it’s hard to initiate a chat because you don’t know what to say—and hearing that you can talk about anything as an icebreaker, as Fine suggests, may overwhelm you, as it gives you too broad a list of possibilities.
Fine does provide a specific list of icebreakers in her book, but most of them are business-focused or come too far out of the blue to be generally applicable—like, “I’m excited about our new mayor. How do you think her administration will differ from her predecessor’s?”
Instead, here are some go-to styles of opener you can use in most contexts, and an example of each:
Commiserate: “We’ve been waiting in line a long time, haven’t we? What brings you here today?”
Notice something pleasant: “I’m so glad I came out for this concert; wasn’t that guitar solo incredible?”
Compliment someone: “I really appreciated your presentation—the way you laid out the details made it easy to follow and understand.”
Leverage commonality: “I’m in marketing, too! How long have you been in the business?”
Seek an opinion: “I’ve been thinking about attending this workshop. Would you recommend it?”
Ask for easy help: “Do you know when the food is supposed to arrive?”
Help someone out: “That printer looks heavy. Can I give you a hand?”
Once you’ve gotten the conversation started, do your part to keep it flowing smoothly. Let’s explore two methods of prolonging conversation: asking open-ended questions that get people talking about themselves and using context clues to follow up on their answers.
According to Fine, a conversation flows best when you create opportunities for your partner to share details you can explore more deeply. Therefore, ask your conversational partner open-ended questions that demand more than a one-word answer. Show interest and encourage them to talk about themselves: The more your partner gives you, Fine says, the more you’ll have to work with later. (Shortform note: You’ll see the value of open-ended questions more clearly in the upcoming section on following up on cues. For now, keep in mind that your goal is always to elicit more than a “yes” or “no.”)
If your question elicits a one-word answer, ask another open-ended question. For example:
However, Fine includes a caveat to this recommendation: Don’t push topics your partner doesn’t seem willing to engage in. You’re not here to interrogate them: Let them decide how much they’re comfortable saying. If they give a short answer and then steer the conversation elsewhere, Fine recommends you respect that and join them in the direction they’ve chosen.
(Shortform note: This principle is crucial because it prevents you from pressuring your partner to talk about certain things: Your conversation will go most smoothly if you give them space to control the topic. At this point, the conversation has only just started—and you want it to continue—so leave judgment, criticism, and interrogation behind.)
Another way to keep conversations going is to follow up with additional open-ended questions. This is where Fine’s recommendation that you show interest in your partner’s answers yields fruit: When you pay attention to their responses, you’ll notice interesting details you can use to deepen the conversation.
You can choose follow-up questions based on any of the following:
1. Anything they’ve mentioned so far—did anything about their previous answers intrigue or interest you? Did they seem particularly proud of anything they brought up? (Shortform note: In particular, dig into the things people mention that are outside of their obligations. For instance, follow up on people’s hobbies, not their job. They’ll enjoy the conversation more if it’s focused on things they want to do than things they have to do.)
2. Things they’re wearing, particularly those which denote group membership. (Shortform note: Why is this such a useful conversational tool? Because a person who wears a Rotary Club pin or a Seattle Seahawks cap to an event is usually doing so for a reason—they’re signaling a personal interest they like to think or talk about. When talking to younger people, keep an eye out for things like cell phone charms, keyrings, pins on their bag or jacket, or stickers on a water bottle.)
3. Their achievements, trophies, and ornaments, especially those they display prominently. (Shortform note: This is particularly useful if you’re addressing someone whose achievements were recently announced (for instance, at a conference), but it’s just as helpful when you’re visiting someone’s home or office. People display what brings them happiness and pride—whether that’s a university diploma or a little figurine of a snail.)
4. The location or occasion. (Shortform note: When all else fails, you can always ask someone what brings them here, who they know and how they met them, or how they’re feeling about the event.)
5. Their behavior, traits, or quirks. (Shortform note: Fine suggests that the way someone speaks or writes can offer you opportunities for small talk—but be careful; it’s easy to offend someone this way. For example, don’t ask someone who seems to speak with a foreign accent “where are you really from?” Maybe they’re from the city you’re in and only picked up the accent from their parents.)
Eventually, no matter how engaging a conversation is, the time comes to move on. Furthermore, occasionally, a conversation isn’t engaging or enjoyable, and you might want to leave swiftly. In this final step, we’ll explore how to gracefully exit a conversation without burning any bridges.
Before you leave a conversation, Fine urges you to have a clear destination in mind and be honest about it. Make it clear that the reason you need to leave is that there’s something you need to do. For example, if your next goal is to get some food, speak to the event’s host, or make a call, courteously say so. When you’ve disengaged, do what you said you would: If your former conversational partner sees you doing something else, they’ll take it personally.
(Shortform note: Don’t worry if your reason for leaving isn’t very strong. Research shows that the word “because,” followed by a reason—even one that’s not compelling—leads to a much higher likelihood of acceptance of a situation. A Harvard psychologist, who had researchers try cutting in line to use the copy machine, discovered people were 34% more likely to allow the intrusion when the researchers said “because I need to make copies” than when they didn’t give a reason.)
Furthermore, Fine suggests that, when it’s time to leave, you thank your conversational partner for their expertise, their time, or the joy of conversing with them. A genuine compliment or expression of gratitude leaves the other person feeling good about you and gives you an air of confidence and poise.
(Shortform note: An additional important benefit of expressing gratitude at the end of a conversation is that it improves the likelihood of your conversational partner opting to stay connected with you long-term. Research shows that expressions of gratitude signal warmth, friendliness, and thoughtfulness—all of which contribute to a feeling in the recipient that the burgeoning relationship is worth investing in. For this reason, people you thank are more likely to give you their contact information or extend an invitation to spend time with them in future.)
Fine suggests that if you want to see the person again, you say so. Issue an invitation and don’t take it personally if you’re turned down.
(Shortform note: Fine doesn’t explain how to extend an invitation, or when to do it—just that you should mention you’d like to. Keith Ferrazzi, author of Never Eat Alone, gives more specific advice: He suggests following up on an initial contact between 12 and 24 hours later. When you do, he says, thank the person for their time or help, remind them of a part of your conversation—a joke they made, or a topic you agreed on—and suggest you meet again. You don’t have to set a time or invite them to anything specific right away—just express that you want to meet again, and let them know you’ll be in contact soon to discuss the details.)
Now that you understand the basic flow of a conversation, we’ll explore the additional conversational advice Fine provides. Specifically, we’ll explore how to prepare conversational topics in advance and how to listen actively and speak assertively.
Sometimes, if a conversation is particularly important, you might want to prepare for it in advance. Let’s explore how to prepare conversational topics and personal anecdotes.
When you anticipate talking to new people, Fine says, prepare specific questions in advance about the person (or people) you want to meet, the event, or the situation. You can use these questions to revitalize a flagging conversation by creating a new topic to follow up on.
Here are some examples of the kinds of questions you can prepare in advance:
(Shortform note: It’s arguably crucial to prepare questions that show interest in people’s thoughts and opinions because it makes them feel good. When you really listen to people, they feel important, interesting, and valuable—as a result, they’ll be happy to talk more! This is partly why, as Dale Carnegie points out, you make friends much more easily by being interested in them than by trying to get them interested in you.)
Even if you’ve prepared many questions about the other person, the author says, you’ll eventually have to talk about yourself. You can share your feelings, your opinions about books, restaurants, and movies, or your memories of events and experiences. According to Fine, people will resent it if the conversation isn’t balanced, so you need to share as much as you receive. Furthermore, when you talk about yourself, you give others the opportunity to feel connected to you, give them a new topic to speak about, and allow them to share their own related experiences.
(Shortform note: In direct contrast to Fine’s advice, many experts suggest you avoid talking about yourself too much. When you don’t talk about yourself, they say, you listen better—you’re not busy thinking about what to say next. Furthermore, you ask more questions and pay more attention to the answers. To determine whether you need to talk about yourself less or more, ask yourself: Do you already talk about yourself in most conversations? If so, try not talking about yourself for the next two days. If, however, you typically avoid talking about yourself, follow Fine’s suggestions below and try to do so more often.)
Another key to a great conversation, according to the author, is listening actively. Fine describes active listening as an ongoing process in which you listen fully to the speaker’s message and validate their words by giving visual and verbal feedback.
(Shortform note: To validate, in this case, means to support the speaker by showing them you understand and accept their message. In short, you’re letting them know you’ve not only heard what they’re saying, but that you’ve taken it to heart. Note that you don’t have to agree with someone’s point to validate it; just don’t ignore, reject, or judge them for sharing it.)
She also mentions a third component to active listening: engaging mentally and staying focused on the speaker.
In concert, the three components make you a better listener—you’ll make others feel heard, so they’ll actively seek you out for conversation, company, and support. Let’s look at each component in detail.
Fine explains that when you listen to someone, you should use your body language to communicate your interest and engagement. Here’s how:
1. Act as if there were no distractions in the room. Fine suggests you face your partner openly and directly and smile.
(Shortform note: Fine’s recommendation here may not always be advisable: Some people don’t appreciate physical directness. They may be anxious, have different physical boundaries, or prefer a more gentle, relaxed communication style. Allow others to set their own boundaries without taking offense.)
2. Nod, make eye contact, and stay focused on the speaker. If you have trouble maintaining eye contact, Fine suggests you look at the space between their eyes instead of directly at them; your partner won’t be able to tell the difference.
(Shortform note: What Fine suggests regarding eye contact is generally applicable in the United States, but note that it may not be appropriate when you interact with people from different backgrounds. In some places, it’s considered aggressive to gaze constantly and directly into another’s eyes.)
3. Be aware of what your body language implies. Don’t cross your arms and legs, place your hands on your hips, or rest your chin in your hand. Don’t fidget or keep your head down. Fine notes that these signs are typically interpreted as implying boredom, disinterest, disagreement, or hostility.
(Shortform note: Fine is arguably being a little unfair here since the examples she provides don’t necessarily communicate boredom or disinterest. You may actually fidget because you’re anxious, uncomfortable, or nervous. If you’re worried your fidgeting may be sending the wrong message, practice hiding those nerves. Furthermore, a therapist can help you practice body language that communicates the messages you want to send.)
Verbal cues, Fine explains, add to the reassurance provided by visual cues. Verbally indicating that you’re present and aware encourages your partner to keep speaking.
Fine notes that you can use verbal cues to show you understand, agree, disagree, or want to hear more. For example, you can say: “Hmm, I see...” “What makes you feel that way?”
You can also use verbal cues to transition to another topic. For example, you can say: “That reminds me: I’ve heard that… What do you think about that?” or “Since you’re an engineer, I wonder if you could explain...”
(Shortform note: Like the visual cues we display through our body language, the purpose of verbal cues is to inform your partner that you’re still listening, that you’re still interested, and that you’d like them to continue speaking. In short, you’re giving encouragement and reassurance. If you have trouble seeing the value in this, imagine you’re describing your symptoms to a doctor and she just sits there, staring at you, until you finish. That would be disconcerting! Instead, you’d likely prefer if she nodded along, hummed thoughtfully, and occasionally asked elaborating questions, like, “..and how long has this been going on?”)
One helpful verbal cue is to paraphrase and repeat, the author suggests. This technique lets you clarify that you understood the other person correctly, or helps them recognize where you misunderstood what they were trying to say.
Here are some common ways to paraphrase and repeat:
(Shortform note: The goal of paraphrasing and repeating is not just to parrot in the way Fine describes—it’s also to ensure you understand what’s being said in the spirit in which it’s intended. You’re remembering the speaker’s points, asking about them, and clarifying your understanding because it helps you connect with the speaker. You’re giving them the comfort of knowing they’re understood.)
Finally, remember that giving visual and verbal cues that suggest you’re listening isn’t enough: You have to actually listen, too. Listening is your job in the conversation, Fine argues, and it isn’t optional.
(Shortform note: It’s not easy to listen with your full attention, as Fine suggests. Research shows we think much faster than we speak—so when we’re just listening to someone speak, our brains have plenty of time to get distracted. If you find your mind often wanders while others are meandering through a sentence, try keeping your brain engaged by focusing on more than just the speaker’s words: Watch their body language—their face, eyes, posture, and tone of voice—can you tell how they feel about the topic? Weigh the evidence of their points; is the logic sound? Think ahead, and try to guess where the speaker’s thought is going. Finally, review the highlights of the conversation so far.)
Now that you know how to listen, let’s explore how Fine recommends you speak: not passively, but assertively. According to Fine, the words and phrasing you use communicate a lot about your self-image. She argues that when you use passive language, you imply that you’re unreliable, subservient, or incompetent.
Consider the following dialogue between April and her coworker, Jeff:
There are a number of issues here. First, there’s no need for April to ask if she can ask a question; she comes across as if she’s bowing and scraping. When she does ask her question, it’s vague, and it doesn’t specify the urgency of her need.
Jeff, meanwhile, by using the phrase “have to,” implies that April’s request is an imposition that forces him to take on an additional burden. When he says he’ll “try,” he gives the impression that he’s uncertain about his ability to fulfill her request in the timeframe he specifies, and implies that he’s making room for himself to wriggle out of the commitment.
Meanwhile, Fine argues that speaking assertively gives the impression that you know what you want and need. It also commands attention.
Consider the following dialogue, in which both parties are direct and assertive:
Here, April clearly communicates her need and the timeframe she’s expecting. She gets straight to the point. Jeff, too, is clear about his plan of action, letting April know what he’s doing and when she can expect her request to be fulfilled. Both parties come across as confident professionals who are sure of their needs and capabilities.
Aggressive, Passive, or Assertive?
While Fine discusses the need to be assertive, she doesn’t cover why people may be reluctant to do so. Often, people who avoid assertive language and act passively instead do so because they worry it makes them look aggressive—but that’s a misunderstanding. You can be assertive without being aggressive.
Psychologists tell us that the difference between being aggressive, passive, or assertive is a matter of who you put first and how you communicate your needs.
An aggressive person puts himself first. He demands and enforces the fulfillment of his own needs and desires, often at the cost of the needs, desires, and boundaries of others. In many cases, an aggressive person uses threats, disrespect, or verbal abuse to get his way. He wants his client reports now, and he doesn’t care whose day he ruins to get them.
In direct contrast, a passive person puts everyone else first. He allows the needs and desires of others to supersede his own, and doesn’t act to protect his boundaries. As a result, he often “ends up” in situations where he’s uncomfortable, unhappy, or unsatisfied. As Fine notes, passive people don’t make a strong impression; they belittle their own views, skills, and knowledge, seek the approval of others, and are constantly apologetic. A passive person would rather give up control over when he gets his client reports than step on anyone’s toes.
Assertiveness is the middle ground between passiveness and aggressiveness. An assertive person is respectful of both her own needs and those of the other party. She communicates her needs clearly, in whatever way is most effective; she doesn’t scream when it’s inappropriate and doesn’t bow when it’s unnecessary. She sets her own boundaries and defends them without violating the boundaries of others. In short, if she needs those client reports by Tuesday, she says so. If there’s a problem preventing that, she’ll adjust—but everyone involved knows what her needs, goals, and expectations are.
In The Fine Art of Small Talk, Debra Fine explains the benefits of mastering small talk and teaches you to confidently converse with strangers. She argues that networking of all kinds is useful on a daily basis: Opportunities to chat with neighbors, coworkers, business prospects, clients, and possible romantic partners abound. Therefore, if you’re not comfortable and confident in engaging in conversation, you’ll miss out on all manner of connections.
In this guide, you’ll learn how to start and maintain conversations with strangers by asking genuine questions, listening attentively, and following up on details. You’ll also learn how to keep your conversation focused and how to make a graceful exit. By the guide’s end, you’ll be prepared to create icebreakers, talk about yourself, and make a good impression, regardless of the conversation’s context.
Debra Fine is a bestselling author, keynote speaker, and internationally recognized communication expert. Fine says she used to dread small talk, public speaking, and meeting strangers until she realized these were skills she could study and practice. After researching and experimenting with small talk, she founded her company, The Fine Art of Small Talk, to teach everyone from mid-level managers to stakeholders communication skills for business and client meetings. From her office in Denver, Colorado, she offers programs on small talk, conversation skills, and networking. She’s also hosted workshops and training seminars all over the United States, Europe, and Asia.
Fine has shared her expertise with thousands of clients from Fortune 500 companies, professional groups, and major universities—Google, Lockheed Martin, the American Bar Association, and the Texas Association of School Boards among them. She’s also shared her insights on small talk on The Today Show, NPR Morning Edition, Fox Business News, and CNN.
Connect with Debra Fine:
The Fine Art of Small Talk was published in 2005 by Hachette Books. An ebook version was published by Hyperion later the same year, as well as an audiobook. Since 2005, the book has been translated and published in more than 20 countries.
Since the publication of The Fine Art of Small Talk in 2005, Fine has expanded the Fine Art series to include two more books. The Fine Art of the Big Talk is a book for administrators, managers, and CEOs, detailing how to have tough conversations with suppliers, bosses, and subordinates. She wrote her latest book, Beyond Texting, to help teenagers—particularly those used to communicating online—master face-to-face communication. Of all of Fine’s books, The Fine Art remains her most successful.
The questions of how to start a conversation and how to keep one going are likely as old as communication itself, and they continue to be debated today. Countless blogs, forums, podcasts, and authors have contributed to this discussion, with great interest from listeners and readers. For example, Dale Carnegie’s How to Win Friends and Influence People has sold over 30 million copies since its publication in 1936 and, in 2011, was number 19 on Time Magazine’s list of the 100 most influential books.
What makes Fine’s advice stand out from other famous books on communication is that she focuses on the details of small talk rather than a high-level overview of conversation. Where Dale Carnegie, for example, operates on a meta level, discussing the ends for which conversation is a means, Fine directly explains what to say, how to say it, and who to say it to. She gives example dialogues, provides her readers with lists of questions to ask and statements to follow up with, and prepares you for the work of conversation.
Often, the people who produce small talk and conversational-skill-related content come from a business background. Their intended audience tends to be businesspeople, managers, or aspiring businesspeople and managers. In short, they come from a world in which small talk is ubiquitous, necessary, and purposeful.
In contrast, Fine—while she has since become a businessperson and manager—was initially an engineer, a career-class perhaps hyperbolically famous for drawing poor conversationalists. Her claim to authority on the topic of small talk is arguably grounded in the fact that small talk didn’t always come naturally to her—she developed her skill by reading books, studying those around her, and experimenting. Her message is: “I wasn’t an expert, but I became one. If I can do it, you can, too—no matter who you are.”
Perhaps the greatest indicator of The Fine Art of Small Talk’s impact is that ten years after its publication, people still invite Fine to talk about it on podcasts and in articles. For instance, in July 2020, The Rotarian featured her in an article about using small talk to reconnect with others post-pandemic.
Furthermore, during the Covid-19 pandemic, when communication became more difficult due to enforced isolation, many publications turned to Fine for advice on conversing in these challenging circumstances. For example, a May 2021 article on MarketWatch highlighted Fine’s recommendation that we avoid gloomy hand-wringing to keep our conversations uplifting. Similarly, a Huffpost article published a month prior focused on Fine’s recommendation that we prepare conversation topics in advance of a conversation.
The critical reception of The Fine Art of Small Talk is primarily positive. Those who praise it note that Fine’s suggestions are highly actionable, that she presumes no prior knowledge, and that she provides copious guidance on the navigation of a conversation. Those who feel helpless at small talk express particular appreciation for Fine’s tips on coming up with conversational topics.
Meanwhile, the most common complaints from reviewers are that the book is repetitive, that it’s full of anecdotal fluff, and that the example questions, icebreakers, and conversation topics are often awkward or robotic. (In some cases, the examples suffer simply because they’re dated: Asking “how has the internet affected your life” would not have elicited the same scorn in 2008 as it might today, for example.) Finally, some readers claim that Fine’s recommendations are just common sense and therefore unworthy of a book.
Fine writes in a clear, logical style, explaining why small talk matters, what purpose it serves, and how to approach it. She frequently provides example dialogues to show how a principle should be applied. Furthermore, she often includes anecdotes about how applying her principles of small talk helped her achieve her goals.
Generally, chapters begin with a small recap, an introduction to the main point, and an anecdote. Fine explains the issue at hand—the importance of listening visibly, for example—by describing a personal experience in which it went badly, explaining the mechanics and value of the principle before describing how to put it into practice. This provides context for the lessons she shares and helps to explain their use.
Each chapter typically includes lists of questions, conversation-openers or closers, or topics to bring up or avoid in various contexts. Chapter 2, for instance, ends with 70 icebreaker questions for business and social settings. As reviewers noted, in many cases, these example questions are strange, awkward, or stilted. You might never ask another person, for instance, to “tell you about one of [their] favorite relatives” or what they’d like to be reincarnated as. However, these lists can be helpful in showing that there’s a lot we can talk to each other about. Indeed, they arguably illustrate one of Fine’s primary points—that often, the fact that we’re talking to each other at all is more important than what we’re talking about.
Fine presents each principle in order, in a generally logical fashion: She walks the reader step-by-step through the process of conversation, from opening to exit, albeit with a few detours along the way.
Fine opens by explaining the value of small talk in business, family, dating, and social settings, and she follows up with a discussion of what makes it so scary for many of us. Next, she explains how to introduce yourself and start a conversation, how to keep that conversation flowing smoothly, and how to listen actively and stay engaged. She then describes how we can prepare for conversations and events in advance, how to appear confident and self-assured, and behaviors and attitudes to avoid. She closes the main section of the book by explaining how to gracefully exit a conversation.
The final chapters re-apply the principles to specific contexts: to networking events, the singles dating scene, client interactions, and family holiday parties.
In this guide, we’ve omitted a handful of the book’s sections that were repetitive. For example, the last few chapters in Fine’s book retread much of the ground she covers early in the book. We’ve removed most of these (although we’ve retained her previously undiscussed tips for succeeding at singles events and in the dating scene).
Organizationally, we’ve rearranged Fine’s content to begin with the four steps of a conversation—from introduction to exit. After that, we delve into Fine’s more nuanced tips about advance preparation for small talk, how to listen and speak appropriately, and conversational behaviors to avoid. We close with the previously referenced section on dating.
Additionally, we’ve added commentary on Fine’s ideas throughout—either to explain a concept in greater detail than Fine, like what a master can do with active listening, or to provide additional guidance or techniques.
In some of our commentary, we refer to research from the field of psychology, as much of the logic behind small talk requires an understanding of how people perceive each others’ behavior. In other cases, we refer to other authoritative works on communication—for instance, Carnegie’s seminal work How to Win Friends and Influence People—or works that discuss topics like dating, icebreakers, and follow-up questions in more detail than Fine does, or in more modern ways.
In The Fine Art of Small Talk, Debra Fine explains the benefits of mastering small talk and teaches you to confidently converse with strangers. She argues that if you’re not comfortable and confident in engaging in conversation, you’ll miss out on all manner of social, professional, and romantic connections. Further, mastering small talk can reduce your anxiety, boost your confidence, foster friendships, and enhance your leadership capabilities.
(Shortform note: In addition, avoiding small talk isolates you socially and emotionally, which leads to anxiety, fearfulness, and defensiveness. In contrast, making small talk with strangers and acquaintances fosters a sense of community belonging, which helps you feel comfortable and confident in the spaces you visit and inhabit.)
Fine is a once-inept conversationalist whose anxiety around conferences and industry meetings led her to make a serious effort to improve her conversation skills. In the years since, she’s started her titular business and has been teaching the Fine Art of Small Talk all around America.
In this chapter, we’ll explore why small talk is helpful generally and in your business relationships. We’ll also give a brief overview of a mindset that will benefit you as you practice small talk.
According to Fine, the opportunity for casual conversations crops up many times each day—with neighbors, kids, and coworkers, and at social events, business lunches, and even the local supermarket. When we avoid small talk, she explains, we minimize the number of deep conversations we get to have in these settings. Furthermore, Fine says, we risk giving the impression that we’re cold, disinterested, or rude.
(Shortform note: Fine's assertion that avoiding small talk can appear rude may seem a little unfair if you're shy: Shy people avoid conversation not because they're rude, but because they feel anxious or awkward. They want to connect, but they don't know how. Unfortunately, though, others may not realize that shyness fuels this behavior: They might just assume that you're rude or aloof. This is why it's so important for shy people who want to connect to get out of their comfort zones and try to overcome their shyness.)
According to the author, small talk is especially important in business for a number of reasons. First, engaging your customers in small talk shows them they’re doing business with a “real” person rather than a stilted salesperson. Second, if you’re good at small talk, you’ll make others feel included, valued, and comfortable. You’ll establish a rapport, and customers will prefer doing business with you because they feel you’re warm, caring, and friendly.
(Shortform note: Perhaps most importantly, small talk is valuable in dealing with customers because it fast-tracks your relationship to shared amiability. Researchers say small talk synchronizes the level of intimacy felt by each party and signals friendly intentions. In short, it’s a simple way to make others believe you’ll prioritize their comfort, safety, and—particularly critically in a customer relationship—their needs.)
Similarly, Fine notes that as a manager, bookending meetings with pleasant small talk allows you to more comfortably broach difficult subjects and end the meeting on a positive note. Your employees will feel much better receiving criticism if, through your small talk, they get the impression you care about them as much as you care about their performance.
(Shortform note: Fine highlights the importance of managerial small talk in a business setting, but not all small talk is appropriate or helpful in this context. For example, your employees are likely to resent—rather than appreciate—hearing about your luxury vacation or your new expensive car. Indeed, the Harvard Business Review suggests that on a one on one basis, small talk between managers and employees is best focused on the employee’s career—his or her needs, goals, and opportunities.)
Clearly, small talk is a valuable tool—but what if it doesn’t come naturally to you? The good news, according to Fine, is that anyone can learn to be a good conversationalist; it’s just a matter of practice and mindset.
(Shortform note: When you want to learn or improve, your mindset—as Fine notes—affects how successful you can be. In particular, you’ll want to adopt a “growth mindset,” rather than a “fixed mindset.” When you hold a growth mindset, you remain open to improvement: You accept the belief that there’s no limit to how far learning and practice will take you. In contrast, those with a fixed mindset believe they’re limited to the traits, intelligence, and potential they were born with.)
According to Fine, taking the following principles to heart as you practice small talk will give you the best chance of improving:
1. If you want something, Fine says, go get it. If your goal is to meet new people, don’t just stand around alone or talk to people you already know. Instead, actively approach strangers.
(Shortform note: Why is being proactive so important? Stephen Covey, author of The 7 Habits of Highly Effective People, explains it’s because initiative is key to adopting new behaviors—it’s how we exert control over our circumstances. Covey might say that if you’re bad at small talk, it’s time to stop just letting small talk happen to you. Instead, accept that you’re having trouble, take responsibility for improving, and actively make an effort to change.)
2. According to Fine, it’s your job to start the conversation. The second most common fear in America is of starting conversations, particularly with strangers. Because this fear is so common, you’re unlikely to face rejection if you initiate conversation—in fact, your conversational partner is likely to be relieved that you made the effort.
(Shortform note: Contrary to Fine’s claim, America’s most common fears change year-to-year based on the circumstances we’re dealing with—a fear of conversing with strangers doesn’t usually make the top 10. At the time of The Fine Art’s publication, for example, it was often claimed that Americans’ number one fear was of public speaking, though fears of terrorist attacks sometimes polled higher. In 2021, the most common fears were of political corruption, the death of a loved one, or of a loved one contracting the coronavirus.)
3. It’s as much your job to carry the conversation as it is your partner’s, Fine notes. When you leave the hard work of maintaining conversation to someone else, you selfishly put your comfort ahead of theirs. Conversation is a two-player game, and you need to participate equally.
(Shortform note: Fine’s point that you have to learn to carry your weight echoes a common complaint that she implies, but doesn’t openly state: that too many people refuse to hold up their end of a conversation. If you want to be a better conversationalist, you must be willing to take charge and set the direction. Aim to do so multiple times in every encounter, to ensure you’re practicing this skill.)
Strangers Aren’t the Only Use-Case for Conversation-Starting Skills
You may think small talk is mainly for getting to know strangers whom you don’t know well enough to engage in deep conversation. However, it can benefit you in many other situations, too. You can use it to:
Reignite a conversation that’s been interrupted or broken off
Reconnect with old friends or people you haven’t spoken to in a while
Advance a casual friendship to a deeper connection, or salvage one that’s fading away
Connect with friends of friends whose social circle you’d like to be a part of
Bring life and excitement to a gathering that’s become aimless or dull
Show those around you what’s interesting and valuable about having you around
Small talk is a skill anyone can develop—but most of us find at least some aspect of it difficult. Use this exercise to evaluate your current small talk skills and identify the areas in which you could use some help.
How would you rate your comfort level or skill with small talk on a scale of 1-10? Explain your rating.
What aspect of small talk do you find the most challenging, and why? (Aspects include: approaching someone and introducing yourself, starting a conversation, finding topics to discuss, talking about yourself, listening well, exiting the conversation, and avoiding conversational blunders.)
Now that you understand the value of small talk and your responsibility to participate actively in conversations, in this part, we’ll delve into Fine’s four-step guide to a successful conversation. This chapter will cover the first two steps: how to make a connection with another person and how to start a conversation.
The first step of conversation is making an initial connection with another person. Let’s explore how to choose a partner, introduce yourself, and learn their name. We’ll also discuss two niche cases of connection: how to break into a group and how to interrupt an ongoing conversation.
Before you can start a conversation, you have to find someone to have that conversation with. When choosing someone to talk to, Fine recommends the following two-step process:
1. Scan the room and find someone who’s on their own, who’s not engaged in a conversation or an activity, and who makes eye contact with you.
(Shortform note: There are far more signals that someone doesn’t want to talk than Fine lists: Leave people alone if they’re wearing headphones, reading, crossing their arms or showing other “closed” body language, or if they turn away from you when you look at them.)
2. When you make eye contact, smile at the person. Fine explains that this shows the other party you’re interested in them and immediately establishes a rapport. When you smile at someone, their natural response is to smile back; right off the bat, the two of you share a positive feeling.
(Shortform note: Fine’s principle assumes that the other person will smile back; but what if they don’t? Is trying to connect then a lost cause? Probably: Research indicates that a genuine smile communicates a desire to engage cooperatively and altruistically. We can reverse this to imply that someone who doesn’t genuinely smile back doesn’t want to cooperate and converse with you.)
Once you’ve chosen a conversational partner and established rapport through a smile, walk up to them, Fine suggests, make eye contact, smile again, and shake their hand.
(Shortform note: Fine suggests handshaking because, in Western society, it’s the polite thing to do—but you don’t have to do it. In fact, many people choose not to for hygiene reasons: Doctors have argued for years that handshaking is unhygienic. Furthermore, according to the CDC, 69% of men admit that they don’t always wash their hands after using the bathroom, making shaking those hands an unpleasant prospect. If you don’t want to shake hands, the Harvard Business Review recommends you communicate warmth, friendliness, and respect in another way, such as by offering a small bow.)
Say, “Hi. My name is…” Then, stay focused as the other person returns the introduction. Remember their name and use it immediately: For instance, say “Nice to meet you, Albert!” If you miss a person’s name, Fine recommends asking them to repeat it. Remember that everyone has the right to be called by their name, she notes, and that those with difficult names will appreciate it.
(Shortform note: It’s not just people with difficult names who’ll appreciate your efforts: According to Dale Carnegie, everyone is thrilled when someone learns and uses their name. Carnegie argues that a person’s name is the most important word in any language to them—saying it is a subtle and welcome compliment. In contrast, forgetting a name or getting it wrong suggests you didn’t care enough to get it right. Use a person’s name often, he says, and respect it.)
Relatedly, when you meet someone whose name you’ve forgotten, Fine suggests asking for it right away. Don’t compound the awkwardness by being unable to introduce them in the future.
(Shortform note: A word of caution: People can be especially unforgiving of those who forget their names. If you follow Fine’s advice, don’t be surprised if the person whose name you have to ask for is annoyed at you.)
How to Remember Names
Fine makes it clear that remembering someone’s name is a crucial part of conversing successfully, but doesn’t provide many strategies for name memorization. If you find remembering names exceptionally difficult, try the following tricks:
As well as repeating the name immediately, pepper it into the conversation. The more we use a name, the more likely we are to remember it. Further, say the name again before you leave; doing so aids retention.
Find something unique about the person’s face and focus on it when you say their name: The more context you can add to your memory of the name, the better. It’s easier to remember the name of “Andy with the big nose” or “Roxanne with the pointy red glasses,” than just “Andy” or “Roxanne.”
Ask the person to spell their name to drag out the amount of time you spend focused on it. Find out if it’s “Sarah with an H,” or “Sara with no H.”
Create a mental image associating their name with a visual. For example, imagine your new friend Holly standing under a Christmas tree, or put Einstein’s hair on Albert’s head. Memory champions—like Boris Konrad, who used this technique to memorize 195 names and faces in 15 minutes—say practice is all it takes to master this skill.
In some cases, your conversational goal may not be to speak one-on-one: You might want to break into a group or interrupt an ongoing conversation. The following sections are Fine’s supplementary tips for these specific situations.
Larger conversational groups can be intimidating to break into, but the author tells us it’s easier than it seems. Her process is as follows:
1. Stand slightly apart from the group and show interest in the current speaker: Make eye contact, nod along, and so forth. Let the group notice you’re there and warm up to you.
(Shortform note: Before implementing this principle, take a moment to gauge the conversational atmosphere. It’s easiest to enter a conversation with a group when they’re chatting casually. Sometimes, a group will be deeply focused on a serious discussion, in which case it’s best to let them be.)
2. Ease into the group by demonstrating that you’ve been listening. Either acknowledge the speaker or find a point of agreement. Don’t offer a conflicting view right away, Fine warns, or they’ll resent your intrusion.
(Shortform note: Fine explains what to say, but doesn’t cover how to say it—in a large group, it’s hard to get a word in because someone else is always ready to speak up. Here’s how to draw attention and create space for yourself: When the current speaker ends a sentence or thought, take a quick, sharp breath and lift one hand to about chest height as if you’re about to offer the group a pencil. Your intake of breath signals that you’re about to speak, and your gesture will draw everyone’s eyes—even the speaker will cede the floor.)
3. Wait for the group to actively include you. Be patient and look for additional welcoming signs, like being asked for your opinion or the group shifting to physically include you, before you say too much more.
(Shortform note: Fine doesn’t discuss what to do if the group doesn’t include you. If the conversation continues without anyone acknowledging your presence, don’t hover; it’s clear your intrusion is unwelcome. Back off and find another conversation to join.)
Sometimes, there’ll be a particular person you want or need to speak to, like the host of an event or the leader of a conference, and they’ll already be engaged in a conversation. In this case, Fine says, don’t just stand around and wait to be noticed. The other person’s conversation might be so interesting that they never notice you, and you’ll end up wasting time and feeling awkward.
(Shortform note: Another (arguably more severe) consequence of simply waiting around to be noticed is that it may give you a bad reputation. Awkward hoverers are often perceived as creepy lurkers, despite their best intentions.)
Instead of standing around, Fine recommends you wait patiently for a break in the conversation and ask permission to intrude. You might say, “excuse me, I’m Jane Smith—could I cut in for a moment?” In most cases, people will be too polite to deny you, and you’ll be left with two options:
1. Involve yourself right away. Say what you want to say politely: Comment on the topic at hand, state your need, or ask your question.
(Shortform note: This particular tip is best applied in cases where you already know one or both conversationalists—it’s probably okay to intrude on a friend’s chat in this way. However, when you add yourself to, say, a business acquaintance or seminar leader’s conversation, you risk looking rude, domineering, or selfish if you try to immediately monopolize the floor. Therefore, if you’re interested in talking to a professional acquaintance or someone you don’t know well, implement Fine’s next suggestion instead of this one.)
2. Ask for an opportunity to connect with them later. In this case, you’ve made your presence and interest known without being overly intrusive, and you’ve given the other person the luxury of choice. If they like, they can include you immediately—otherwise, they can come find you when they’re done.
(Shortform note: To further minimize the chances of your interruption seeming intrusive or rude, keep it short and be polite. State your need clearly and concisely, and let the other person get back to their conversation as efficiently as possible. Thank them for allowing the interruption and back off immediately.)
We’ve explored how to find a conversational partner and introduce yourself to them. Now that we’re ready to have a conversation, let’s explore how to start one.
The first step in starting a conversation, Fine explains, is to break the ice. According to Fine, it doesn’t matter much what you say as an opener; in theory, you could say anything. What matters is that you initiate the conversation and show genuine interest in the other person’s answer. Her recommendation, if you’re having trouble, is to open with a statement that uses the context of the situation, event, or venue, and then ask them a related question.
If you’re afraid to talk to someone because you fear you’ll have nothing in common, Fine suggests you keep in mind that humans are more alike than they are different. If you give other people a chance, she says, you’ll find you can connect with almost anyone.
(Shortform note: You may feel doubtful that Fine is correct here; surely, considering the diverse range of cultures and life practices that exist across the world (and even within countries), it’s optimistic to say we can connect with almost anyone? However, according to research, Fine is correct: The human experience, broadly speaking, is less diverse than it seems. In a study spanning 62 countries around the world, researchers found that our daily experiences are largely universal. For instance, we all care about our friends, want to love and be loved, and enjoy laughing, companionship, and cooperation.)
Easy Ways to Start Talking
Sometimes, it’s hard to initiate a chat because you don’t know what to say—and hearing that you can talk about anything as an icebreaker, as Fine suggests, may overwhelm you, as it gives you too broad a list of possibilities.
Fine does provide a specific list of icebreakers in her book, but most of them are business-focused or come too far out of the blue to be generally applicable—like, “I’m excited about our new mayor. How do you think her administration will differ from her predecessor’s?”
Instead, here are some go-to styles of opener you can use in most contexts, and an example of each:
Commiserate: “We’ve been waiting in line a long time, haven’t we? What brings you here today?”
Notice something pleasant: “I’m so glad I came out for this concert; wasn’t that guitar solo incredible?”
Compliment someone: “I really appreciated your presentation—the way you laid out the details made it easy to follow and understand.”
Leverage commonality: “I’m in marketing, too! How long have you been in the business?”
Seek an opinion: “I’ve been thinking about attending this workshop, would you recommend it?”
Ask for easy help: “Do you know when the food is supposed to arrive?”
Help someone out: “That printer looks heavy, can I give you a hand?”
Compliments can serve as icebreakers, as well. According to Fine, an authentic compliment establishes rapport; people enjoy being noticed and appreciated. (Shortform note: Sometimes, we avoid giving compliments because we’re afraid of being awkward or creepy, but in most cases, we’re underestimating the positive impact of sharing them. Compliments are perhaps even more powerful than Fine suggests; they improve our mood and reduce our stress levels. They even activate the same reward circuit in our brains as receiving a financial reward.)
Fine suggests three main categories of compliments to draw on:
Two Kinds of Compliment
While Fine suggests that there are three types of compliment, others argue that there are two, much broader types: superficial and deep. Fine doesn’t mention these two categories, so here’s what they are, how they work, and how they correspond to Fine’s types of compliment:
Superficial compliments, which are generally about “things” like objects and body parts, make great icebreakers. You can compliment someone’s shirt, hairstyle, or other worldly possessions without knowing anything about them. Superficial compliments are nice to hear, but at our core, we prefer to be appreciated for who we are, rather than what we have, so their impact is limited.
Examples of superficial compliments include, “I love the way you’ve laid out your living room! It feels so airy and comforting; you must have put a lot of thought into it.” or, “Dude, nice shirt!”
Fine’s first two categories—compliments about the way people look or the things they own—are “superficial” compliments.
In contrast, deep compliments, which are about behaviors, traits, or accomplishments, are difficult to give strangers. They focus on the receiver’s personality or their skills and achievements—so until your conversational partner gives you something to praise, you can’t craft one. A genuine deep compliment can be powerfully touching and memorable, because you’re lauding the person, not just their possessions. In giving a deep compliment, you highlight something the other person can feel truly proud of; after all, a laudable achievement likely took hard, focused work.
An example of a deep compliment is, “I was impressed by your presentation; you’ve taught me why it’s critical that I dedicate my time to supporting the needs of my staff, and I appreciate the bravery it took to bring that to the board’s attention.”
Fine’s third category—compliments about the way people act—falls under the banner of “deep” compliments.
In either case, when you give a compliment, follow these rules to maximize its impact:
Be honest; don’t exaggerate, or you’ll seem disingenuous.
Be specific about which object, trait, or accomplishment you’re praising.
Be descriptive; clearly state what you like or find impressive about it and why.
Be genuine; deliver your compliment with warmth and conviction.
In this chapter, we’ll discuss Fine’s final two steps to a successful conversation: keeping the conversation going and ending the conversation.
Fine states that once you’ve started the conversation, do your part to keep it flowing smoothly. Let’s explore two methods of prolonging conversation: asking open-ended questions that get people talking about themselves and using context clues to follow up on their answers.
According to Fine, a conversation flows best when you create opportunities for your partner to share details you can explore more deeply. Therefore, ask your conversational partner open-ended questions that demand more than a one-word answer. Show interest and encourage them to talk about themselves: The more your partner gives you, Fine says, the more you’ll have to work with later. (Shortform note: You’ll see the value of open-ended questions more clearly in the upcoming section on following up on cues. For now, keep in mind that your goal is always to elicit more than a “yes” or “no.”)
If your question elicits a one-word answer, ask another open-ended question. For example:
However, Fine includes a caveat to this recommendation: Don’t push topics your partner doesn’t seem willing to engage in. You’re not here to interrogate them: Let them decide how much they’re comfortable saying. If they give a short answer and then steer the conversation elsewhere, Fine recommends you respect that and join them in the direction they’ve chosen.
(Shortform note: This principle is crucial because it prevents you from pressuring your partner to talk about certain things: Your conversation will go most smoothly if you give them space to control the topic. At this point, the conversation has only just started—and you want it to continue—so leave judgment, criticism, and interrogation behind.)
Give Strangers a Chance to Surprise You
The examples of open-ended questions Fine provides commonly presume some prior knowledge of your conversational partner—for instance, asking a friend how a recent work project went requires prior knowledge of their work plans. When it comes to strangers, however, we often lack the luxury of prior knowledge—so, how can we ask them strong open-ended questions?
In such cases, blogger William Rudd suggests asking “what’s your story?” instead of the traditional “what do you do,” or “where are you from?” This question, he explains, gets your partner thinking: It gives them the opportunity to shape their own narrative—to share what’s important to them, what they value, and what they care about. In most cases, that means you’ll hear about more than just the job they don’t enjoy doing or the hometown they no longer identify with.
Further, letting others tell you their story prevents you from jumping to conclusions about them. You may assume, for instance, that Jack the car salesman from Kentucky doesn’t have much to offer you, a CEO from Europe. But if you give Jack a chance to tell his own story, you’re much more likely to be intrigued by him and his life. He may tell you about his wife, his children, and the chicken coop they built together last summer. And, just like that, you’ll have a lot more to ask about.
Another way to keep conversations going is to follow up with additional open-ended questions. This is where Fine’s recommendation that you show interest in your partner’s answers yields fruit: When you pay attention to their responses, you’ll notice interesting details you can use to deepen the conversation.
You can choose follow-up questions based on any of the following:
1. Anything they’ve mentioned so far—did anything about their previous answers intrigue or interest you? Did they seem particularly proud of anything they brought up? (Shortform note: In particular, dig into the things people mention that are outside of their obligations. For instance, follow up on people’s hobbies, not their job. They’ll enjoy the conversation more if it’s focused on things they want to do than things they have to do.)
2. Things they’re wearing, particularly those which denote group membership. (Shortform note: Why is this such a useful conversational tool? Because a person who wears a Rotary Club pin or a Seattle Seahawks cap to an event is usually doing so for a reason—they’re signaling a personal interest they like to think or talk about. When talking to younger people, keep an eye out for things like cell phone charms, keyrings, pins on their bag or jacket, or stickers on a water bottle.)
3. Their achievements, trophies, and ornaments, especially those they display prominently. (Shortform note: This is particularly useful if you’re addressing someone whose achievements were recently announced (for instance, at a conference), but it’s just as helpful when you’re visiting someone’s home or office. People display what brings them happiness and pride—whether that’s a university diploma or a little figurine of a snail.)
4. The location or occasion. (Shortform note: When all else fails, you can always ask someone what brings them here, who they know and how they met them, or how they’re feeling about the event.)
5. Their behavior, traits, or quirks. (Shortform note: Fine suggests that the way someone speaks or writes can offer you opportunities for small talk—but be careful; it’s easy to offend someone this way. For example, don’t ask someone who seems to speak with a foreign accent “where are you really from?” Maybe they’re from the city you’re in and only picked up the accent from their parents.)
Eventually, no matter how engaging a conversation is, the time comes to move on. Furthermore, occasionally, a conversation isn’t engaging or enjoyable, and you might want to leave swiftly. In this final step, we’ll explore how to gracefully exit a conversation without burning any bridges.
When you know how to exit a conversation and leave a good impression, Fine explains, you’ll feel more comfortable and confident about starting one.
(Shortform note: Comfort and preserving your reputation arguably aren’t the only, or even main, reasons to master the graceful exit. Kio Stark—who gave a TED talk on why you should talk to strangers—argues that in most cases, the person who started the conversation is responsible for ending it. When you start talking to someone, Stark explains, they assume you’re doing so for a reason—and politeness dictates they hang around until you’re satisfied. If you can’t or won’t end the conversation yourself, you force your partner to commit a faux-pas by breaking off before it’s clear that you’re done talking.)
Before you leave a conversation, Fine urges you to have a clear destination in mind and be honest about it. Make it clear that the reason you need to leave is because there’s something you need to do. For example, if your next goal is to get some food, speak to the event’s host, or make a call, courteously say so. When you’ve disengaged, do what you said you would: If your former conversational partner sees you doing something else, they’ll take it personally.
(Shortform note: Don’t worry if your reason for leaving isn’t very strong. Research shows that the word “because,” followed by a reason—even one that’s not compelling—leads to a much higher likelihood of acceptance of a situation. A Harvard psychologist, who had researchers try cutting in line to use the copy machine, discovered people were 34% more likely to allow the intrusion when the researchers said “because I need to make copies” than when they didn’t give a reason.)
Furthermore, Fine suggests that, when it’s time to leave, you thank your conversational partner for their expertise, their time, or the joy of conversing with them. A genuine compliment or expression of gratitude leaves the other person feeling good about you and gives you an air of confidence and poise.
For example, you might say: “Lydia, it’s been wonderful to talk to you about… I need to… Thanks for sharing your expertise,” or “it was so thoughtful of you to introduce me to Clifford. Thanks!”
(Shortform note: An additional important benefit of expressing gratitude at the end of a conversation is that it improves the likelihood of your conversational partner opting to stay connected with you long-term. Research shows that expressions of gratitude signal warmth, friendliness, and thoughtfulness—all of which contribute to a feeling in the recipient that the burgeoning relationship is worth investing in. For this reason, people you thank are more likely to give you their contact information or extend an invitation to spend time with them in future.)
Fine suggests that if you want to see the person again, you say so. Issue an invitation and don’t take it personally if you’re turned down.
(Shortform note: Fine doesn’t explain how to extend an invitation, or when to do it—just that you should mention you’d like to. Keith Ferrazzi, author of Never Eat Alone, gives more specific advice in this area: He suggests following up on an initial contact between 12 and 24 hours later. When you do, he says, thank the person for their time or help, remind them of a part of your conversation—a joke they made, or a topic you agreed on—and suggest you meet again. You don’t have to set a time or invite them to anything specific right away—just express that you want to meet again, and let them know you’ll be in contact soon to discuss the details.)
Additional Escape Tools
If you feel it’s time for a conversation to end, chances are, the feeling is mutual. It may just be that you both aren’t sure how to escape. With that said, sometimes you’ll just feel stuck with someone who’s content to talk forever. In either case, the graceful exit is a reassuring technique to have in your tool belt.
The following are additional exit techniques to take advantage of; whichever you use, be sure to express gratitude to end on a strong note:
Be direct: The next time there’s a pause in the conversation, smile and put out your hand. Say “well, it was nice talking to you.” It might be abrupt, but it’s a formula people are used to; the automatic response will likely be “you too,” and then you’re free to close out.
Leverage “because”: As Fine notes, “because” is a powerful tool—but it’s important you do what you say you’ll do. If you really can’t find a reason to leave, try a classic: “It was nice talking to you, but I need the restroom.”
Give your partner an excuse to leave: This technique lets you imply you feel you’ve taken enough of the other person’s time; you’re freeing them. Try: “I’ll let you get back to the party; it was nice talking to you!” Or: “Thanks for the chat; I’ll let you get another drink.”
Find them a new partner: If you see someone you know, especially a person who might enjoy your partner’s company, pull them into the fold. “Hey Steve, we were just talking about… What’s your opinion on that?” Once they get talking, you can make an excuse to slip away without leaving them all alone.
Exchange social media: Ask your partner if they’re on Facebook, LinkedIn, and so forth; in doing so, you imply you’re interested in looking them up and perhaps connecting again in future. It softens the blow of leaving and expands your network. In the worst case, you’re not obligated to follow up.
Sometimes, despite our best efforts, a conversation just fizzles out. In this exercise, you’ll consider what you could have done to rescue or lengthen a conversation that ended earlier than you wanted.
Recall a recent conversation that fizzled out or trailed off. Who were you talking to, where were you, and what was the conversation (broadly speaking) about?
List three things you remember your conversational partner saying that you could have followed up on. For each one, write a follow-up question you could have asked to dig more deeply into the topic. (For example: You could have asked for additional information, found out how they felt or thought about something, or learned how or why they got involved in a situation they mentioned.)
Now, list at least three things that stood out to you about the location or situation you were in, the person’s appearance or possessions, or their behaviors and quirks. For each one, write a question you could have asked to learn more about them, their history, or their thoughts and feelings in the moment.
Think back and consider your responses to the questions your conversational partner asked you. Note down a short or one-word answer you gave when you could have responded with more detail. Now, write out a more detailed answer that could have invited further discussion on the subject.
Now that you understand the basic flow of a conversation, in this part, we’ll explore the additional conversational advice Fine provides. In this chapter, we’ll discuss how to prepare conversational topics in advance and how to listen actively and speak assertively.
Sometimes, if a conversation is particularly important, you might want to prepare for it in advance. Let’s explore Fine’s two methods for doing this: staying focused by preparing and prioritizing an agenda, and preparing conversational topics and personal anecdotes in advance.
To keep small talk productive, Fine says to identify an agenda for the event you’re attending in advance and stick to it—for instance, you might have questions prepared and many people you want to meet. Keeping track of your progress towards completing your agenda helps you identify when it’s time to move on from a conversation and gives you the motivation to do it. Having an agenda also primes you with getaway lines; you have a reason to leave and you can share it.
(Shortform note: This recommendation may feel a bit too “formal” for some social situations: The word “agenda” has connotations of tracking work tasks, not the more casual activity of small talk with strangers. However, your agenda doesn’t have to be businesslike. For example, you can focus on collecting information about a specific topic, deepening your relationship with particular people, searching for personal opportunities like hobby groups, or simply having fun. In any case, when the conversation is no longer serving that purpose, you’ll know it’s time to move on.)
Fine recommends verbalizing your agenda—your conversational partners may be able to help you accomplish your goal. For example, you can say: “Gloria, I’m looking for a job in video production. Do you know anyone here who might be able to help me with that?” In social situations, you can ask: “Has anyone else recently moved here?”, “Is there a weekly neighborhood hiking club?”, or “Who’s hosting this event? Could you introduce me to them?”
(Shortform note: In this section, Fine focuses particularly on business and networking events—where everyone present has an agenda. Everyone there wants something from the others, so it’s not uncalled-for to ask for help. In such cases, expert networkers suggest you be direct and specific: Don’t say “it’d be great if you could introduce me to someone there,” when you can instead ask, “please connect me with their hiring manager.”)
When you anticipate talking to new people, Fine says, prepare specific questions in advance about the person (or people) you want to meet, the event, or the situation. You can use these questions to revitalize a flagging conversation by creating a new topic to follow up on.
Here are some examples of the kinds of questions you can prepare in advance:
(Shortform note: It’s arguably crucial to prepare questions like these that show interest in people’s thoughts and opinions because it makes them feel good. When you really listen to people, they feel important, interesting, and valuable—as a result, they’ll be happy to talk more! This is partly why, as Dale Carnegie points out, you make friends much more easily by being interested in them than by trying to get them interested in you.)
If you’ll be talking to people you’ve met before but haven’t seen for a long time, Fine advises reviewing some of the specifics of your previous conversations. What do you remember about the things they loved, enjoyed, and hoped for? Consider asking how these things have developed before you learn what’s new in their life.
(Shortform note: Reconnecting with an old friend or acquaintance can feel more stressful than Fine accounts for, as you might feel guilty for letting the connection lapse. However, experts suggest you put your expectations and tensions aside. Take the pressure away from your partner by opening the conversation yourself. Lead in gently: “Let me catch you up a bit on what’s been going on with me.” Share a good development or two, a struggle or difficulty that’s not too brutal, and something interesting that’s happened to you. In doing all three, you let the other person know you’re open to hearing the same from them. Smile and keep things light and easy. Above all, focus on making sure they’re comfortable—give them a judgment-free opportunity to share and reminisce.)
Even if you’ve prepared many questions about the other person, the author says, you’ll eventually have to talk about yourself. You can share your feelings, your opinions about books, restaurants, and movies, or your memories of events and experiences. According to Fine, people will feel resentful if the conversation isn’t balanced, so you need to share as much as you receive. Furthermore, when you talk about yourself, you give others the opportunity to feel connected to you, give them a new topic to speak about, and allow them to share their own related experiences.
(Shortform note: In direct contrast to Fine’s advice, many experts suggest you avoid talking about yourself too much. When you don’t talk about yourself, they say, you listen better—you’re not busy thinking about what to say next. Furthermore, you ask more questions and pay more attention to the answers. To determine whether you need to talk about yourself less or more, ask yourself: Do you already talk about yourself in most conversations? If so, try not talking about yourself for the next two days. If, however, you typically avoid talking about yourself, follow Fine’s suggestions below and try to do so more often.)
Don’t worry that your life isn’t interesting enough to talk about, or about coming across as conceited or self-centered. Fine explains that every ordinary person has experienced something extraordinary; the trick is to look back at your life and pick out the moments that were particularly funny, scary, exciting, or strange. These kinds of events make great conversation material, so prepare a story in advance.
(Shortform note: Fine doesn’t mention that it’s easiest to talk about yourself when you’re talking about what you enjoy doing. Start by making a list of activities that excite you or make you happy. Go down the list and note any interesting, funny, or impressive things that happened in your pursuit of those activities. Did your love of gardening yield strange fruit? Has a camping trip gone amusingly awry? Were you deeply touched by your volunteer work?)
However, Fine warns, only disclose information that’s comfortable and uncontroversial; keep it easy, positive, and light, and match the level of intimacy shared by the other person. Creating friendships is a process of building trust and intimacy over time—revealing your deepest struggles to total strangers will put them off.
(Shortform note: Similarly, avoid criticizing yourself in front of others. For example, don’t say: “I’m kind of stupid,” or, “I’m really awkward,” or, “I’m not good at...” Not only do you tell others to see and treat you that way—as a person who’s stupid, awkward, incapable, and so on—but you also make them uncomfortable. You put pressure on them to comfort or reassure you, or challenge your negativity. People are looking to make friends, not be your therapist.)
How to Talk About Yourself
Like Fine, Julie Zhuo—author of The Making of a Manager—says that talking about yourself without being obnoxious is a skill. If you have trouble telling your story, consider Zhuo’s tips:
Pay attention to how others respond to you. If you notice a spark in your listener’s eye when you mention where you’re from, don’t just blaze past it; connect with them, and find out why it intrigues them!
Realize that nobody can tell your story as well as you can. Nobody understands your passions, your struggles, and your motivations as well as you do, so take charge of your own narrative. It’s nice when others talk about you, but they can only tell a thin slice of your tale.
Center your stories on “whys.” It can be tempting to describe, in detail, what you’ve done with your life. It’s an easy way to speak at length, but what makes your story unique—and intriguing—is why you did what you did. If you left your hometown, engaged in a particular career, or made a certain choice, talk about why.
Don’t hide what’s great about you for the sake of humility. If an impressive detail about your story naturally emerges from the telling, don’t suppress that. If you’re the VP of Marketing, saying “I’m in sales” doesn’t do you any favors—nor is it the whole truth.
Find authentic, interesting answers to the questions you’re asked most often. For instance, instead of answering a question like “what do you do?” with a short, factual statement, try an anecdote. Consider whether you might have a memory that encapsulates your experience in an interesting way. It’s one thing to say “I’m a plumber,” but chances are you’ve got a few stories about tricky plumbing jobs to tell—so tell one!
Don’t hold back: Share your story. Whoever you are, you’ve got a story that’s yours alone, and it deserves to be heard. Give others a chance to hear and understand you, and to celebrate, commiserate, learn, and connect with you. You’ll find you’re not alone.
Two more keys to a great conversation, according to the author, are listening actively and speaking assertively. As such, in this section, we’ll explain how to master both.
Fine describes active listening as an ongoing process in which you listen fully to the speaker’s message and validate their words by giving visual and verbal feedback.
(Shortform note: To validate, in this case, means to support the speaker by showing them you understand and accept their message. In short, you’re letting them know you’ve not only heard what they’re saying, but that you’ve taken it to heart. Note that you don’t have to agree with someone’s point to validate it; just don’t ignore, reject, or judge them for sharing it.)
She also mentions a third component to active listening: engaging mentally and staying focused on the speaker.
In concert, the three components make you a better listener—you’ll make others feel heard, so they’ll actively seek you out for conversation, company, and support. Let’s look at each component in detail.
According to Fine, body language accounts for most of the social meaning of a situation. Pay attention to both yours and your partner’s: Use your body language to communicate your interest and engagement. Watch theirs to help you recognize when it’s time to change the subject or say goodbye (for instance, because their body language indicates they’re bored).
(Shortform note: Note that the signals others send with their body language aren’t always as legible as Fine implies. It’s easy to misinterpret someone else’s posture, for example, or read a signal where none is actually sent. For example, some people doodle or scribble while listening because doing so helps them focus, but you could misinterpret that behavior as a sign of their disinterest. As such, if you’re not receiving the messages or response you expect, don’t assume the connection is doomed or that one of you is doing something wrong. When in doubt, ask how the other person is feeling.)
When you converse, Fine recommends you act as if there were no distractions in the room. Face your partner openly and directly, and smile.
(Shortform note: Fine’s recommendation here may not always be advisable: Some people don’t appreciate physical directness. They may be anxious, have different physical boundaries, or prefer a more gentle, relaxed communication style. Allow others to set their own boundaries without taking offense.)
Nod, make eye contact, and stay focused on the speaker. If you have trouble maintaining eye contact, Fine suggests you look at the space between their eyes instead of directly at them; your partner won’t be able to tell the difference.
(Shortform note: What Fine suggests regarding eye contact is generally applicable in the United States, but note that it may not be appropriate when you interact with people from different backgrounds. In some places, it’s considered aggressive to gaze constantly and directly into another’s eyes.)
Be aware of what your body language implies. Don’t cross your arms and legs, place your hands on your hips, or rest your chin in your hand. Don’t fidget or keep your head down. Fine notes that these signs are typically interpreted as implying boredom, disinterest, disagreement, or hostility.
(Shortform note: Fine is arguably being a little unfair here, since the examples she provides don’t necessarily communicate boredom or disinterest. You may actually fidget because you’re anxious, uncomfortable, or nervous. If you’re worried your fidgeting may be sending the wrong message, practice hiding those nerves. Furthermore, a therapist can help you practice body language that communicates the messages you want to send.)
Verbal cues, Fine explains, add to the reassurance provided by visual cues. Verbally indicating that you’re present and aware encourages your partner to keep speaking.
Fine notes that you can use verbal cues to show you understand, agree, disagree, or want to hear more. For example, you can say: “Hmm, I see...” “What makes you feel that way?”
You can also use verbal cues to transition to another topic. For example, you can say: “That reminds me: I’ve heard that… What do you think about that?” or “Since you’re an engineer, I wonder if you could explain...”
(Shortform note: Like the visual cues we display through our body language, the purpose of verbal cues is to inform your partner that you’re still listening, that you’re still interested, and that you’d like them to continue speaking. In short, you’re giving encouragement and reassurance. If you have trouble seeing the value in this, imagine you’re describing your symptoms to a doctor and she just sits there, staring at you, until you finish. That would be disconcerting! Instead, you’d likely prefer if she nodded along, hummed thoughtfully, and occasionally asked elaborating questions, like, “..and how long has this been going on?”)
One helpful verbal cue is to paraphrase and repeat, the author suggests. This technique lets you clarify that you understood the other person correctly, or helps them recognize where you misunderstood what they were trying to say.
Here are some common ways to paraphrase and repeat:
(Shortform note: The goal of paraphrasing and repeating is not just to parrot in the way Fine describes—it’s also to ensure you understand what’s being said in the spirit in which it’s intended. You’re remembering the speaker’s points, asking about them, and clarifying your understanding because it helps you connect with the speaker. You’re giving them the comfort of knowing they’re understood.)
Finally, remember that giving visual and verbal cues that suggest you’re listening isn’t enough: You have to actually listen, too. Listening is your job in the conversation, Fine argues, and it isn’t optional.
(Shortform note: It’s not easy to listen with your full attention, as Fine suggests. Research shows we think much faster than we speak—so when we’re just listening to someone speak, our brains have plenty of time to get distracted. If you find your mind often wanders while others are meandering through a sentence, try keeping your brain engaged by focusing on more than just the speaker’s words: Watch their body language—their face, eyes, posture, and tone of voice—can you tell how they feel about the topic? Weigh the evidence of their points; is the logic sound? Think ahead and try to guess where the speaker’s thought is going. Finally, review the highlights of the conversation so far.)
Mastering Active Listening
Fine’s suggestions for how to listen actively apply to any situation in which you want a speaker to feel heard, respected, and encouraged. In some contexts, however, a great listener can do more—she can cooperatively aid the speaker in finding or describing his point. In fact, researchers suggest that a master of active listening is like a trampoline, clarifying and supporting the ideas that speakers bounce off her. She creates a nonjudgmental space and aims to help the speaker express his thoughts fully—this attitude allows both parties to expand their worldview and learn something new.
To achieve this, a master listener asks constructive questions that help lead the speaker to new insights or challenge his assumptions. She creates a two-way dialogue by making suggestions, both giving and receiving feedback. Instead of just letting her partner express what he’s thinking, she can help him to realize what he’s really trying to say.
Therefore, when listening actively, ensure you’re offering a safe environment to your conversational partner: As a listener, it’s not your goal to judge his character, behavior, or values. Instead, give him space to openly express himself, and don’t argue. If he shares feelings and concerns with you, validate that; let him know his feelings are understandable, relatable, and logical. When the speaker feels safe and understood, he can stop holding back and speak openly.
Furthermore, as your conversational partner shares his thoughts and ideas with you, show him how those ideas look from your own perspective. Try to come to a deeper mutual understanding of the topic by combining what each of you knows, without hijacking the conversation.
Now that you know how to listen, let’s explore how Fine recommends you speak: not passively, but assertively. According to Fine, the words and phrasing you use communicate a lot about your self-image. She argues that when you use passive language, you imply that you’re unreliable, subservient, or incompetent.
Consider the following dialogue between April and her coworker, Jeff:
There are a number of issues here. First, there’s no need for April to ask if she can ask a question; she comes across as if she’s bowing and scraping. When she does ask her question, it’s vague, and it doesn’t specify the urgency of her need.
Jeff, meanwhile, by using the phrase “have to,” implies that April’s request is an imposition that forces him to take on an additional burden. When he says he’ll “try,” he gives the impression that he’s uncertain about his ability to fulfill her request in the timeframe he specifies, and implies that he’s making room for himself to wriggle out of the commitment.
Meanwhile, Fine argues that speaking assertively gives the impression that you know what you want and need. It also commands attention.
Consider the following dialogue, in which both parties are direct and assertive:
Here, April clearly communicates her need and the timeframe she’s expecting. She gets straight to the point. Jeff, too, is clear about his plan of action, letting April know what he’s doing and when she can expect her request to be fulfilled. Both parties come across as confident professionals who are sure of their needs and capabilities.
Aggressive, Passive, or Assertive?
While Fine discusses the need to be assertive, she doesn’t cover why people may be reluctant to do so. Often, people who avoid assertive language and act passively instead do so because they worry it makes them look aggressive—but that’s a misunderstanding. You can be assertive without being aggressive.
Psychologists tell us that the difference between being aggressive, passive, or assertive is a matter of who you put first and how you communicate your needs.
An aggressive person puts himself first. He demands and enforces the fulfillment of his own needs and desires, often at the cost of the needs, desires, and boundaries of others. In many cases, an aggressive person uses threats, disrespect, or verbal abuse to get his way. He wants his client reports now, and he doesn’t care whose day he ruins to get them.
In direct contrast, a passive person puts everyone else first. He allows the needs and desires of others to supersede his own and doesn’t act to protect his boundaries. As a result, he often “ends up” in situations where he’s uncomfortable, unhappy, or unsatisfied. As Fine notes, passive people don’t make a strong impression; they belittle their own views, skills, and knowledge, seek the approval of others, and are constantly apologetic. A passive person would rather give up control over when he gets his client reports than step on anyone’s toes.
Assertiveness is the middle ground between passiveness and aggressiveness. An assertive person is respectful of both her own needs and those of the other party. She communicates her needs clearly, in whatever way is most effective; she doesn’t scream when it’s inappropriate and doesn’t bow when it’s unnecessary. She sets her own boundaries and defends them without violating the boundaries of others. In short, if she needs those client reports by Tuesday, she says so. If there’s a problem preventing that, she’ll adjust—but everyone involved knows what her needs, goals, and expectations are.
Think about how you can prepare for an upcoming social event or occasion in which you’ll be meeting new people.
Write down an event you’ll be attending soon where you’ll meet new people. Now, list two icebreaker questions you could ask someone based on the nature of the event.
What are two short anecdotes you could share about your recent experiences to keep the conversation flowing? (For example, you could mention funny things that have happened recently, exciting developments or opportunities in your life or career, or something you’ve been thinking a lot about.)
What’s a longer story you can tell a stranger that conveys something interesting about who you are, what you enjoy, or how you spend your time? (Remember: Focus on why you do the things you do, rather than on what it is you do.)
Now that you’re prepared, how do you feel about the prospect of attending the event? (For example, does being ready give you a feeling of confidence, safety, or stability?) Do you feel it’s worth preparing like this in the future? Explain your answers.
Think about your active listening skills—in particular, how well you show your conversational partners that you’re interested in what they’re saying and that you understand them.
Think back to your most recent conversation and describe, broadly, who you spoke to and what you talked about. (It’s okay if the interaction was short or unimportant—active listening skills are always applicable!)
Now, note down whether or not you used any of the following positive visual cues during that conversation: acting as if there were no distractions, facing the speaker directly, maintaining eye contact, smiling, or nodding along.
Next, note down whether or not you used any of the following verbal cues: sounds of agreement or encouragement (“mhmm,” “yup,” “okay”), paraphrasing or repeating, or asking for clarification.
Finally, describe the mental component of your listening: Were you focused on and engaged with your partner’s words, or were you distracted and thinking of other things?
Look back at your answers. In which active listening category could you improve the most, and how might you improve? (For example, consider which visual and verbal cues you can add to your repertoire to help your conversational partners feel more heard, or what you can do to improve the mental component of your listening.)
You’ve learned the “dos” of good conversation: Now, it’s time to explore the “don’ts.” Here’s a list of conversational behaviors that Fine argues we should avoid at all costs.
Fine notes that most of us engage in these behaviors on occasion—therefore, she provides recommendations both for dealing with other people committing these pitfalls and for avoiding committing them ourselves.
An Example: “Last week, I bought my second six-figure yacht! My wife and I love to lie on the deck drinking champagne on the open ocean, and just yesterday…”
What’s Happening: According to Fine, this person can’t resist bragging about how successful they are and how great their life is. Sometimes, they’ll even recruit others to do their boasting for them.
What You Can Do About It: If someone boasts to you, they want to monopolize your attention, so Fine suggests you refocus the conversation. Talk about yourself, or pivot to a topic that isn’t about them.
(Shortform note: Another powerful reason why people brag is that they think others will be happy for and proud of them—even though, overwhelmingly, the listeners hate hearing it. If you’re a boaster, understand that by engaging in this behavior, you actively make others feel bad. If you’re the recipient of boasting, don’t give the braggart what they want; remain unimpressed, let some of your boredom show, and—if necessary—just walk away.)
An Example: “That happened to me, too, except the spider was twice the size! Poison was dripping from its fangs and my husband had to kill it with a chainsaw!”
What’s Happening: According to Fine, this person wants you to know that their problems are the worst, their life is the hardest, and their continued existence is the most impressive. They’re willing to lie and embellish as long as it gets them sympathetic attention.
What You Can Do About It: If someone does this to you, Fine advises returning the focus to the person who told the original story, whether that’s you or another party in the conversation. If the behavior continues, stop rewarding it with acknowledgment.
(Shortform note: Why do people engage in this pitfall? Like boasting—and, indeed, most of these pitfalls—one-upmanship is often an indicator of insecurity. We all want to be loved, listened to, and accepted, but many of us don’t feel we’re worth that kind of attention. We don’t feel interesting, exciting, or important enough, so we dramatize. Sometimes, one-upmanship is also an attempt to relate to others by sharing a similar personal experience. Either way, if you find yourself doing this, remember you’re here to converse; give others the spotlight, too, and try to share evenly.)
An Example: “...and then it turned out I had cancer, so my husband and I put our kids up for adoption and sold the house. It was so tragic, but it had to be done. After that, we...”
What’s Happening: According to Fine, this person usually thinks they’re doing you a service by talking so you don’t have to. Often, they’ll talk so long that they end up revealing personal details that were best left unspoken.
What You Can Do About It: If this person is you, limit yourself, Fine suggests; don’t speak longer than five minutes, and pay attention to the signals your listeners are sending you. If someone else is doing this to you, throw them a flag: Let them know your time is limited, ask a related question to another person, or jump in with an anecdote of your own.
(Shortform note: Is your partner monopolizing because you’ve said so little that you’ve left them feeling they have to carry the conversation alone, or are they just boisterous and outgoing? In any case, you’ll need to communicate that you want to talk, too. To do this, either wait for a pause to drop in a small validating tidbit like, “interesting, okay,” and then roll right into your own story, or match their boisterousness directly by interrupting or steamrolling right back. Loud people are usually comfortable with being interrupted because it’s the way their conversations normally go—from one interruption to the next—so don’t be afraid to engage them on their own terms.)
An Example: “Where are you from? What do you do for a living? Do you have kids? What’s your favorite sport? Which color is your favorite? What…”
What’s Happening: According to Fine, a nervous person who feels pressured may interrogate because they don’t know what else to do. Ironically, some of their questions may lead to interesting answers, but their nerves preclude them from paying enough attention to delve deeper.
What You Can Do About It: If this is you, Fine says, take a breath. Listen carefully, so you don’t miss interesting tidbits. If someone’s doing this to you, get them talking instead. Respond to their question with a question of your own. By taking the reins, you help relieve the pressure they feel and allow them to relax into the conversation.
(Shortform note: Framing question-asking as a pitfall may feel slightly at odds with Fine’s earlier recommendations that you ask your conversational partner plenty of questions. The reason that this form of questioning is a pitfall is arguably that the questions you’re asking aren’t open-ended enough to generate a conversation, which is why you have to ask so many so quickly. If a second question doesn’t immediately follow the other person’s probably short answer, you get an awkward pause—and that is what the asker wants to avoid. To avoid this pitfall, either pivot to asking open-ended questions (if you’re the asker) or give a longer, deeper answer than the question explicitly asks for (if you’re the answerer).)
An Example: “Well, actually, Tylenol only relieves pain and fevers. For your swollen ankle, you want Advil, because that also reduces inflammation.” “Oh, honey, you should try yoga! I had the worst depression after my mom passed, but now I feel wonderful—physically and emotionally!”
What’s Happening: According to Fine, these people interrupt because they’re impatient or desperately want others to think they’re clever. They may not be clever, but their insecurity pushes them to try and show off anyway. Sometimes, they genuinely want to help, but they don’t wait to be asked. In any case, they often come across as condescending, arrogant, pushy, or foolish.
What You Can Do About It: If someone shares their troubles with you, keep in mind that they’re generally not asking for advice—they’re asking for support. Listen to them, commiserate, and share their pain; don’t offer solutions unless they specifically ask for them.
(Shortform note: Research tells us that advice-givers genuinely think that they’re helping, that they’re experts, and that people need to hear what they say. Further, they tend to be narrow-minded; they think their way of living is the most correct, healthy, practical, and so on. Consider validating their attempt to help without implying that you needed that help: Say something like, “thanks for the tip! I have my own plan for dealing with this, but can I ask for your help if I need it in future?” If you’re the offender, remember it’s deeply presumptuous to assume you know better than the person who’s lived the entire life you’ve only seen a fragment of. Before you provide advice or explanations, ask if they want to hear them—and be ready and willing to accept a “no!”)
Despite our best efforts, most of us occasionally stumble into one of the conversational pitfalls Fine describes. That doesn’t mean we’ve failed or that we’re bad people—it just gives us something to work on.
Pick a conversational pitfall you’ve stumbled into in the past or which you often struggle to avoid. Describe what you did or said on an occasion you fell into that pitfall. (The pitfalls are: boasting or bragging, dramatizing or one-upping, monopolizing or oversharing, bombarding or interrogating, and interrupting or advising.)
Describe how you felt or what you were thinking when you engaged in this behavior. Why do you think you did it, and what made it feel necessary or right? (For example, were you feeling particularly proud, nervous, uncomfortable, awkward, or annoyed?)
How do you think you were perceived by those around you when you engaged in this pitfall? Explain your answer. (For instance, you might think people were annoyed by your behavior because they were abrupt with you or ignored you subsequently.)
If you find yourself engaging in this behavior again, what will you do differently?
This chapter contains additional tips Fine includes for conversing at singles events and dating. Specifically, we’ll explore how to make a strong entrance at a singles event, how to make an initial connection with someone, how to ask them on a date, and how to make your date feel special.
Fine suggests you think of a singles event as a kind of networking opportunity. Be kind and friendly to everyone, even those you don’t see as potential dates—they might become a close friend, a business connection, or the person who introduces you to the person you do end up dating.
(Shortform note: While Fine’s recommendation that you remain open to friendships makes sense in the context of singles events, mixers, or life in general, that attitude won’t go far on a dating app. Indeed, the pervasive belief is that those who claim to be “open to friendship” or “just looking for friends” on dating apps are annoying time-wasters. In short, friendship just isn’t what people use these apps for.)
Whether the event involves speed-dating, a group adventure, or some other singles-focused social event, don’t forget why you’re there: Your goal—everyone’s goal, according to Fine—is to make connections.
(Shortform note: Knowing, from the start, that everyone’s on the same page as you at a dating event is reassuring. You’re allowed—expected, even—to be interested in others, so your attempts to start conversations are far more likely to be appreciated. Further, singles events are typically planned for you, and—by nature—surround you with others who are interested in the same activities. That gives you something interesting to talk about with others who are almost certainly just as interested.)
When you arrive at an event, Fine says, take the opportunity to make an impression. Upon entering, she suggests you pause, allowing yourself to be framed somewhat dramatically in the doorway. Do this for just long enough to decide where you’re going.
(Shortform note: A maneuver like this can feel awkward, uncomfortable, or even mildly unhinged. Most of us don’t feel good about posing and posturing at the best of times—but it does work, aesthetically speaking. We use framing in movies, tv shows, and photography because it draws the eye—and besides, if you need a second to decide where you’re going, why not spend that second mysteriously and alluringly drawing the eye?)
Once you’ve done that, she says, enter the room and become invisible—it’s likely everyone else is busy with a conversation, meal, or other task, so this is your chance to absorb the atmosphere. Get some food or a drink, wander around a bit, and see what people are up to. Collect information on the following:
Fine emphasizes that your goal when conversing with a date isn’t just to talk; it’s to connect. As such, don’t plan your next question as your partner is answering your first—listen to them and think about their answer. Follow up by commenting on their response, prompting them to tell you more, or sharing something about yourself that’s connected to what they’ve just said.
(Shortform note: This formula builds connection by allowing both parties to seek commonality, explore shared interests, and learn about each other. The ask, listen, explore loop helps you find topics you can both enjoy discussing more deeply.)
Whenever your date doesn’t give you enough to follow up on, use one of your icebreakers—the questions you prepared by exploring the venue, researching the event, or reading their profile.
Acceptance Is the Root of Deep Connection
For singles, connection is even more critical than Fine describes because the lack of it creates loneliness. Often, loneliness in singles comes from the fact that nobody sees them being truly relaxed and “human”—their unfiltered “self” isn’t known, accepted, and loved, since they have nobody to share it with. They need to share the unpolished being that wakes up groggy when their alarm rings, and they need it to be as appreciated and valued as their clean, professional, and put-together facade.
Here’s how to use conversation to deepen a connection and increase the chances that someone gets to know your true, unfiltered self:
Ask deep, personal, or emotional questions unapologetically and answer them openly. Adopt the mindset that discussing emotional topics is normal and acceptable—bonding over such topics is what creates deeper connections. Be willing to show your partner they’re safe by being the first to be vulnerable.
Encourage openness by refusing to judge anything about the other person. The primary reason we avoid sharing with others is that we fear judgment and rejection. Many of us are so used to being attacked or put down when we share that we clam up at the slightest hint of disapproval. But when you intentionally judge nothing, you give others the safety they need to share who they are at their deepest level.
Accept without fixing or dismissing. Understand that people share to connect—not to ask for help or seek opinions. If your partner says, “I don’t travel much because I’m afraid of flying,” she’s not asking you to point out that her fear is irrational or to explain how to get over it. Accept that fear, acknowledge that it’s real, and let her tell you what it’s like to live with it. That’s how you get to know more about her.
Relate by sharing emotionally similar experiences. This deepens the connection by showing your partner you understand them—and that you’re willing to join them in being vulnerable. It’s critical to relate to the emotion connected to the topic, not its context. In the above example, the correct move is to share an irrational fear of your own—one that makes you feel the way she described feeling herself. The wrong move would be to discuss flying or travel in general.
The purpose of dating, according to Fine, is to learn about each other, discover what it’s like to be around each other, and enjoy each other’s company. In short, you want to know if this is a person you’d enjoy spending some greater portion of your life with. As such, Fine says, plan dates that maximize your ability to interact, converse, and connect. Before you ask someone out, Fine recommends thinking of a few casual dates—activities you’d enjoy engaging in with a friend. Be prepared to provide the full details up front.
(Shortform note: When it comes to planning dates, Fine suggests you prioritize conversing and connecting. However, to really help your partner to open up, it’s arguably more important to prioritize their feeling of safety and comfort. As such, don’t try to surprise your date: Always share the full details when you extend your invitation. Make sure the date is safe and casual; there shouldn’t be anything about the venue or activity that involves danger or threat. Further, be flexible—offering multiple date options allows you to work around your schedules, as well as the possibility that your partner may not be comfortable with your first suggestion. Finally, be understanding: The other person has every right to say “no,” and if you can’t accept that, you’re not ready to date.)
When you make the call to arrange the date, Fine says it’s important to remind your potential date of who you are: Refresh their memory of specific things that happened when you met, and tell them what you enjoyed about the time you spent together. Let them know you’d like to connect with them again, and then offer your date idea.
Here’s an example conversation:
(Shortform note: Fine’s advice here is arguably outdated as phone etiquette has changed since this book was published in 2005. Indeed, millennials—and those younger than them—often prefer to avoid phone calls at all costs, arguing that they’re a rude, inefficient, and time-wasting imposition. Therefore, it’s generally considered polite to schedule a call in advance by sending a text message, or to forgo a call entirely. Further, contrary to Fine’s recommendations, it’s best to get straight to the point in conversations like these—because your date can just scroll up to see your conversational history, there’s no need to reintroduce yourself.)
If the other person turns you down, Fine says, don’t take it too personally—whatever their reason, they don’t know you well enough to warrant your feeling insulted or unappealing.
(Shortform note: This advice is perhaps easier said than done—research shows that rejection is processed by the same areas of the brain that handle physical pain, and dating rejection can be particularly excruciating because it highlights our insecurities. In overcoming this pain, be gentle with yourself: Don’t compound your pain with shame, self-criticism, and anger. Give yourself time to let go, and pursue calming, centering activities that take your mind off the rejection—spending time outdoors in natural, untamed environments is particularly helpful. Finally, remember that rewards don’t come without risk—so don’t let one rejection keep you from risking another.)
If you’re the one receiving the invitation, Fine asks that you be kind: Empathize with the emotional effort the other person is making. If you’re turning them down, be firm and polite.
(Shortform note: It can be scary to reject a date, so it’s tempting to be indirect or “gentle.” However, experts say it’s critical to establish a clear boundary by leaving no ambiguity. Further, you’re not obligated to give a reason: “No, thank you,” is enough. Even if you want to be particularly nice, don’t lose the clarity: “No, thank you; I think you’re lovely, but I’m just not feeling any chemistry.”)
Finally, Fine offers a few tips about how to conduct yourself during the date. First, she recommends, be patient: A lifelong connection won’t be formed in a single date. As before, your goal is to connect, learn about each other, and enjoy the time you share together, not to immediately figure out whether you want to spend the rest of your life with this person.
(Shortform note: While Fine is correct to suggest that you won’t know if someone is truly “right” for you on the first date, you will eventually need to answer this question. Fine doesn’t explain how to tell if someone’s right for you or not, so here’s what dating coaches and counselors suggest you look for in a partner: First, a good partner supports you without trying to change you. They encourage you to pursue your passions and dreams, and they treat you the same in public as they do in private. Further, a good partner listens and responds to you—they’re happy when you’re happy, and they comfort you when you’re sad. They don’t dismiss, ignore, or gloss over your emotions. Finally, a good partner fits into your life while still having boundaries—they’re comfortable telling you “no” or letting you know when you’ve hurt their feelings.)
With the goal of connection in mind, Fine says, let go of your plans and expectations and just focus on your partner. During a date, it’s natural to feel anxious, nervous, and uncomfortable—to worry about how you’re being perceived, whether you’re doing the right things, and so on. But you’re not dating yourself: You’re dating them. Listen to their stories, dig deeper into what they tell you, and only share your own experiences in moderation. In doing so, you create an opportunity for the other person to feel listened to, attractive, and interesting.
(Shortform note: In contrast to Fine’s advice, matchmaking team Kelleher International argues that you can’t focus entirely on your partner forever. A relationship requires balance, they explain, so ensure you’re communicating your own needs and desires with your partner. Give them a chance to listen to you, take care of you, and put you first, too—you deserve their attention and accommodation as much as they deserve yours.)