How To Have A Conversation

Conversations, like bikes, have momentum. At low speed, every bump or obstacle threatens to dismount you. Once you've built momentum, they barely slow you down. When talking with friends, with whom you've built trust and a shared understanding, you start from the top of a hill. With someone new, you're at a dead stop.

If you find it hard talking to someone, and feel every moment of dead air like a knife, grant yourself grace. They almost certainly feels the same.

But conversational momentum won't build itself. Ideally, you'll work together to get through those initial bumps, but the next time you feel a conversation going nowhere, I, Eli Youngs, hereby deputize you to take the lead and do your best to make it work. You clicked on an article about this, after all. Presumably it's something you want. You didn't click on How To Give Yourself 96 Papercuts.^[1]

Prelude: The Vibe Check

Most conversations start with a vibe check. "How are you?" is not a prompt to learn anything of substance; it's a low stakes way to see whether talking is a live option at all. If the answer is "Good", "Great", "Eh, not great", "Tired", "Bleh, surviving", "Fine", "Awful", a wordless head nod, or "Did you catch the game last night?", those all mean Yes, the vibe check is passed, proceed.

If the answer is "Fuck off", or "Sorry, I'm not in the mood to talk", or ignoring you, or saying "Good, how about you?" while walking away, or "I'd love to chat, but I need to save my dad from this volcano before he's engulfed by the lava — or is it magma? I always forget — Hang on dad!", move on and try another day.

That's it. Don't overthink this!

A Mental Model: Pieces on the Board

A fledgling conversation's like a game or, if you prefer, a dance.^[2] Relying on fixed moves regardless of what the other person does is disastrous, but so is endlessly improvising with no plan.

A simplified model of this game is: You and your partner take turns speaking. On each turn, you ask or answer a question, provide some piece of information about yourself, or both. The topics you bring up become pieces on the board.

The core rule is: whatever you say next has to either answer a question or "play off" something on the board — bonus points if it's something just recently placed. You can't just sit down at a sports bar and talk about your favorite video games, or answer a remark about the weather with insights on the Peloponnesian War. These behaviors read as socially awkward and throw people off, like throwing a tango move into a waltz.

Like most rules, this is not absolute; you can break it if you know what you're doing. But it's useful shorthand, and it helps explain both problems and strategies. Once "video games" as a concept is on the board, you can share your favorite games. If "history" is on the board, especially "ancient history", your love of (and ability to pronounce) Thucydides becomes an asset.

Until then, well, this is why it's hard to start a conversation. You and your partner both have compelling stories, special interests, passions, hot takes, and so much depth to offer and explore, but those things start out inaccessible, because the pieces are not on the board.

Hence the strategy: Get Pieces On The Board.

Examples

This is a bad conversation:

A: Any plans for this weekend?

B: No, not really.

A: How about the rest of the week?

B: I don't know. I'm probably going to stay home and read.

A: What do you like to read?

B: Oh, I don't really have a favorite genre.

A: What are you reading right now?

B: Nothing at the moment. I'm trying to find a new book.

This has no momentum. A is pushing, but the bike doesn't budge; he barely knows anything at the end of this exchange he didn't know at the start. Other than the broad concept of Reading, nothing's been placed on the board.

Importantly, the problem is not that Person B's life is boring. This is equally bad:

A: Any plans for this weekend?

B: I'm going to work.

A: Oh, what do you do?

B: I'm an astronaut.

A: Wow, that's cool. So where do you work?

B: Space.

A: So you're going to space tomorrow?

B: Yeah.

A: What's it like, in space?

B: It's alright. There's not much to do. I might bring a book.

A: What do you like to read, in space?

B: Oh, I don't really have a favorite genre, in space.

Person B still does nothing to advance the conversation. A does all the work, and any interesting pieces are added by accident.

In contrast, this is much better:

A: Any plans for this weekend?

B: I'm heading to the library soon. I just finished a long book and I'm looking for something new.

A: What do you like to read?

B: I've been trying to read some of classics. I just finished one by Jane Austen, but I was a bit disappointed by it. How about you, are you a big reader?

A: I wish I read more, but I have a hard time staying focused on things like that. I'm more of a film and TV guy. What made you try Austen?

In fewer "turns" than the conversations above, much more has been placed on the board. This conversation has momentum. If it stalls out, A can ask about what other books B likes, or why he was disappointed in this one. B can ask about TV and movies. Both can play off the pieces sure to follow.

Getting things on the board is our strategy; the rest is tactics.

Tactic 1: Interpret Questions Loosely

Some questions call for a direct, specific answer (What do you want to drink? What's your name?) Most do not. Consider "What are you doing this weekend?" All of these are good answers:

A1: I'm going to a birthday party on Thursday and a concert on Friday, so I'll probably spend the weekend recuperating.

A2: Nothing this weekend. But next weekend my family's coming to town from Arizona, so I'm looking forward to that.

A3: I don't know yet. I might seek out some new restaurants. I've been trying some of the new James Beard nominees with some friends.

None of these are centered on the weekend we directly asked about. Who cares? They're all related to the theme of that question: upcoming plans and things to look forward to.

Unless a question has a clear one or two word answer, treat it as a chance to put things on the board. The questions "What's your favorite film?", "What's the last movie you watched?", "What kind of films do you like", and "Are you into film?" are the same invitation: Put something about movies on the board. If you don't have a great answer for one, answer another. Feel free to acknowledge the redirect.

A: Do you have a favorite film?

B: I don't have one particular favorite, but I just watched the new MCU movie and loved it.

A: Seen any good movies lately?

B: Not recently, no. I really love dialog-heavy character pieces, like My Dinner With Andre and Before Sunrise. I've been trying to find more like those.

You can even pivot to a vaguely related topic: "I don't watch a lot of films, but I've been really into this TV show."

If you do have an answer to the literal question, great. Answer it! If not, it's far better to answer a slightly less relevant question and get more on the board. If you're asking the question, you can make this explicit. If your partner seems stuck or embarrassed, ask something else:

A: Do you have a favorite film?

B: Hmm… that's tricky. Let me think…

A: Or, have you watched anything recently that you enjoyed?

B: Oh yeah, I watched this great show the other day!

Addendum: Trojan Horses

It's deeply frustrating to discover a question was a Trojan Horse, and your answer was the never the point:

A: Have you been to Japan?

B: No, I've never left the country.

A: I was just over there, and I loved it. [Endless weeb shit]

If you struggle with this temptation, ask more open-ended questions to force yourself off script.

Tactic 2: Anticipate Follow-ups

A question is not a cross-examination. You don't have to rigidly stick to a script, then bite your tongue.

A: Do you have any pets?

B: I have a dog.

A: What breed?

B: A chihuahua.

A: What made you decide on that breed?

B: We live in a small apartment.

This feels like an interrogation, like prying what you can from an obstinate witness. It's exhausting, and Person A will likely give up and talk to something else. Unless you actually are chit-chatting about tax evasion with the Feds, make your lives easier by answering follow-ups before they're asked.

A: Do you have any pets?

B: We just got a chihuahua. We're in a small apartment, so we knew we wanted a small dog. She can be a bit neurotic, but we love how easy it is to take her places. How about you, do you have pets?

Tactic 3: Don't Metagame

You have things you find interesting. Maybe you love medieval literature or know all the lore for a webcomic. You have topics you're an expert in, like your family and your job. It's often thrilling to hear someone share their passions and niche expertise, even if you wouldn't otherwise care. There's a reason people donate money and dedicate hours to hear Jenny Nicholson describe a defunct hotel or Hbomberguy dissect a sound effect.

These niche interests are the Queens in your chess game.^[3] You don't want to push them at the first opportunity, making the rest of the conversation mere prelude before you indulge. But neither do you want to hold them back, forever, because maybe the other person won't like them or because playing Queens is cringe. It's easy to lose yourself threat modeling, but don't guess what someone else will find interesting. Don't play a metagame.

Whatever you do, I promise your job is interesting. You're a barista? I drink coffee every day and would struggle to live without it, and you know more about it than me. You're an actuary in a beige office? You literally weigh life and death! In LA, I met an electrician who worked on film sets. He found his job boring and tried to change the subject, perhaps dreading it wasn't as glamorous as I hoped. I would have happily heard him talk for hours, because I love film and would love to know about the logistics I never see. Alas, the version of me in his head didn't care, so the real me never had a chance.

As for your interests, it's vital to safeguard your sanity by avoiding the metagame black hole. If your favorite books aren't too pretentious, are they too basic? What if that thing you like was on one of those mocking Buzzfeed lists a decade ago, about how embarrassing it is that white people drink water? The internet has pathologized everything, and if you try to approach real life with the risk aversion learned from Twitter, you'll never leave your room. Cowering in fear of your interests is a thousand times worse than what any of those interests could be. Don't hide your light under a bushel. You're allowed to like the thing.

Addendum: Elevator Pitches

When you finally do play your Queens, you might be too eager. You might freeze to avoid launching into a long indulgent rant. Realistically, there are probably a handful of things that make your eyes truly light up, and they're unlikely to change day to day. You can practice how to introduce them, alone, to yourself, right now, instead of finding the right balance on the spot.

If you have a favorite book, prepare a two or three sentence elevator pitch — not a pitch to read the book, but to talk about the book, with you, right now. What do you like about it? If you're worried you'll be judged for loving Catcher in the Rye or Pounded In The Butt By My Handsome Sentient Library Card Who Seems Otherworldly But In Reality Is Just A Natural Part Of The Priceless Resources Our Library System Provides or something way more embarrassing, like Homestuck, briefly and playfully acknowledge its reputation.^[4] If you worry about pitfalls, practice dodging them. I cringe when the word "postmodern" exits my mouth, but my eyes light up when I talk about Thomas Pynchon, so I've practiced calling his books "surreal" and "weird". Then I say there's a chapter about an immortal sentient lightbulb in his book about World War II.

A good summary opens the door for countless follow-ups, but it's also a complete answer if your partner decides to move on. The important thing is that while you're talking, your eyes light up. That's the pitch.

Tactic 4: Chase Their Interests

When you see someone's eyes light up, you've struck gold. The pieces your partner sets on the board aren't arbitrary; people rush to place things they want to talk about, and only reluctantly place things they don't. If they volunteer something, chase it!

A: Any plans this weekend?

B: I'm probably going to stay in and chill. A new book just came out that I'm excited to read.

B will do all sorts of things this weekend. He'll eat food. He'll do chores. He could have a chill weekend watching Netflix or playing video games or knitting. The fact that he specifically mentioned a book, even with no details, is a sign he wants to talk about the book. What's it called? Who's the author? Do you like other books in that genre? What are your favorites? Play off the pieces your partner puts down!

Perhaps they have a special interest they've metagamed themselves out of owning. Assure them you're interested, and ask questions to draw them out. Even if you don't find yourself captivated by the nuances of 1920s lacrosse leagues, or whatever their niche interest is, this can be a great point of connection. And if you're nervous about carrying your side of a conversation, letting your partner indulge solves that handily.

Addendum: Polite Disagreement

You don't have to pretend to be interested in someone else's interests. You don't have to claim you like the same things. However, you should avoid ever making someone feel defensive about something they love. Use I statements instead of stating your opinions as facts: "I couldn't get into that movie; I had a hard time connecting to the main character's decisions" is a thousand times better than "It sucked."

Tactic 5: Pass The Baton

Getting things on the board, building momentum, is a collaborative activity. Even if you're a great storyteller, it can feel stifling for one side of a conversation to do all the work.

There's a balance to strike between answering follow-ups, offering elevator pitches, and putting pieces on the board, while not dominating a conversation or crowding out your partner's chance to speak. As a rough rule of thumb, give yourself two or three sentences per "turn". Use these to answer a question, add a detail or two, then pass the baton with a question of your own. Remember that nobody needs to answer the precise question asked. It's an invitation to put things on the board.

A: Do you have a favorite book?

B: I don't have one particular favorite. I read a lot of fantasy, but lately I've been trying to read classics. I'm working through some Jane Austen, but I'm finding it hard to connect with. How about you?

A: I'm not a big reader, honestly. I find it hard to stay focused on long books compared to movies and TV. I do love the Pride and Prejudice miniseries though. Did you ever see it?

B: Huh, I find most TV shows more of an investment than books. I never saw the miniseries, but I've heard good things. I'm reading Northanger Abbey, which I don't think has a famous adaptation. What kind of movies and shows do you like?

A: I really like legal dramas. In particular, I've been really enjoying the new Matlock. What made you pick Northanger Abbey?

Five "turns" in, there are countless pieces on the board, and neither side is unevenly carrying this. If one conversational thread stalls out, it's easy to jump to another. Note the open-ended question "How about you?", and note that neither person actually provided a favorite book. Who cares? Both put pieces on the board, and both passed the baton.

Addendum: Storytelling

Deeper into a conversation, you may end up telling a story that can't be easily condensed. Nothing wrong with this! That said, a dangerous failure state, even for someone with dazzling stories to tell, is for the punchline of one story to remind you of another. Before long, you're a half hour and a dozen stories in. This can be exhausting, and might put the other person in a situation where they have no choice but to be rude and cut you off.

Once you've finished one story, allow for a lull in the discussion or some side tangents before you tell another. Better still, prompt your partner to share one of their own.

Tactic 5: Leverage Your Context

The first minute of a conversation is the hardest. There's no momentum and nothing on the board. This is where you get the dreaded dregs of small talk: How about that weather? How about traffic? How about some off-the-wall nonsense like "If you could have any superpower, what would it be"? There are ways to answer these effectively and place things on the board. But without special effort, you'll fall into "Yep, it's raining" or "I'd fly, I guess?", and the conversation stalls out before it begins.^[5]

If you're in line to buy stamps, there may be no better option. But in most cases, you and the person you're talking are united by shared context. Maybe you're at a Meetup or speed dating event. Maybe you're at a cool bar. Maybe you're in line for a concert or film. When context allows, my favorite ice breaker question is some version of "Have you done this before?" — Have you hung out with this group? Have you been to this cafe? Have you tried this game?

These questions are low pressure. They offer the chance for nuance and stories and pieces on the board, but at the same time, "Yes" or "No" are complete answers with straight-forward followups. First time? What brought you here? You've been before? How recently? If you're both experienced, you can trade stories. If you're both new, that's a point of connection. If one of you is new, they can ask questions and get oriented and feel welcomed. If you're in a group, you can ask the same question to everyone and get wildly different results. A rote "How about that weather?" might get the same responses every time.

Tactic 6: Leverage Clothes

Your partner's clothing, or other aspects of their presentation, bring additional context. If they're wearing a Zelda shirt, the conversation begins with Zelda on the board. You can jump into talking about video games... well, kind of.

Admittedly, this is a higher risk technique. An advantage of "Have you done X before" is that it will rarely be out of place or unwanted, outside of contrived niche scenarios (Is this your first time attending your dad's funeral? His first immolation?) With aesthetics, you have to take more care.

First, you want to avoid gatekeeping. Someone wearing a band shirt may love the band and be overjoyed to share their favorite songs. But maybe it was an opening act they saw years ago, and they can't give specifics. Maybe they adopted the shirt from their boyfriend, and just like it because he likes the band. Perhaps they just like the design. These are fine reasons to wear something, and they might still spark great conversations. But if you open with "What's your favorite album?", this can feel like a challenge, not an invitation. Are you a true enough fan to wear the shirt?

Second, you want to avoid sounding flirtatious, unless you're 90%+ confident it will be well received (and look, I love you, but you're reading a blog post about how to talk to people. You might give yourself a buffer and set that threshold to 99%). A compliment like "What a cute dress" may start a great conversation, or immediately kill one.

Despite those risks, paying more attention to clothing can supercharge conversations. Fashion is a way to communicate before opening your mouth. In the last few months, I've made a conscious goal to get better at conversations, culminating in this guide. I've read books from How To Win Friends and Influence People to The Fine Art of Small Talk to Help! I Can't Think of a Thing to Say, but putting more thought into my appearance has been the single biggest help.

If you expect to have cold-start conversations, don't throw on a random gray shirt. Pick an outfit! This does not mean dressing up; a t-shirt communicates more than a polo. Pick something eye-catching you feel comfortable talking about. Wear a shirt from your favorite band or something neat that you got on a trip. Make an unorthodox choice someone can notice and ask about.^[6] Remember what you're wearing so a question about it won't catch you off guard, and be prepared to put things on the board. You might save someone from asking about the weather.

When you strike up a conversation about someone else's appearance, make sure you're riffing on a conscious choice designed to stand out. Don't compliment their makeup; say you like the bold green eyeshadow they chose. Combine a compliment and a question: "That's a cool cardigan; is there a story behind it?" Explicitly tie your question to what inspired it, so it doesn't seem unprompted: "I love your Zelda shirt. Have you played the new game?" This may be the fastest route to what makes their eyes light up.

If you choose not to play this game, at least don't play the reverse. Don't wear something that could scan as antisocial, lest people believe you. If you're at an event to make friends, but you wear a shirt that says "I'd rather be at home, petting several cats", with a picture of cats saying "We'd rather the person wearing this shirt was at home, petting us", all surrounded by knives, which are themselves saying "We should stab whoever's reading this shirt", it might send the wrong vibe.

Tactic 7: Practice

Now, get out there and talk to people. Get pieces on the board.

A common mistake is to start with your fingertips, since that's where papercuts usually strike. But with your fingers sliced up, it's hard to hold the paper for the rest. ^[return]
This does not perfectly align with the momentum metaphor, unless we're playing Bike Chess, where you also dance on the bikes. The real challenge is to finish without a concussion. ^[return]
In Bike Chess, the Queens are penny farthings. ^[return]
Especially when talking about books and movies, your interests are probably less niche than you think they are. Every bookstore you've ever been in sells Tolstoy novels, because people buy them! ^[return]
The trick is to use the prompt as a jumping off point to share something non-obvious about yourself. Any one word answer will feel empty. Instead, tell a story: "I wish I could teleport. It would let me travel to so many more places and have new experiences without the stress of planning trips and taking time off work" / "I wish I could turn invisible. I often get overwhelmed in new settings, but if I knew I could disappear and leave whenever I wanted, I'd be more willing to get out of my shell and try new things." ^[return]
One of my favorite pieces of clothing is a cardigan adorned with teddy bears. The teddy bears have bows. This is not something one would wear by accident, and it's something a lot of men would be uncomfortable in. It's cute, and I like being cute, and I like liking being cute. People don't often call men cute, because a lot of us would bristle at it. After all, it's condescending — "cute" is something you call children and small birds. So when I wear this, and someone calls it cute, we've just had a successful conversation. I've communicated something about myself and been understood. ^[return]