What really makes a conversation is enthusiasm. Be excited to talk to this person, whether that excitement stems from the sheer awesomeness of her existence or from finally having the right audience (her) for sharing something hilarious you saw last night. Don’t try to force it—just be honest. Not to get heavy, but why do you like having this person in your life? They get your jokes, they share the best remixes, they love you and make you feel good about yourself? If something made you think of her, say so. If you miss hanging out with her, say that. Keep in mind that it won’t kill you to use exclamation points every now and then.


Maybe you’re trying to play it cool in front of someone you have a crush on, and your approach is to be the Disaffected Brooding Sensitive Guy. But trust me, this rule of thumb still applies. You can get worked up about something in front of her without giving away your crush. Enthusiasm is contagious, and a very close cousin to charisma. (And charisma is just style plus friendly confidence mixed with super-advanced conversation skills.)

Ask Questions. The all-time best way to start a conversation­—in a three-way tie with an invitation to Kanye West’s birthday party and some variation of I was thinking about you recently—is to simply ask the other person a question about themselves. Most men are really terrible at this. I mean, just piss poor. It’s so bad that pretty much every straight woman I’ve ever known has remarked upon it.


I know that you know how to ask a question, but I’m not convinced you know how to ask a good one. For example, every American is adept at how are you? This is okay in some contexts—checking in on a heartbroken ex, for example—but it’s also one of the laziest, least sincere-seeming inquiries, and laziness is the antithesis of enthusiasm. In fact, it’s a conversation non-starter. I know many, many women (myself included) who’ve been in years-long relationships with men who still don’t bother to ask them questions. You need to make an effort to do this with everyone in your life who matters to you! It’s called emotional labor; step it up.

A good question conveys earnest interest and concern. It includes specifics. If it can be answered with a mere yes or no, that yes or no will easily lead to equally enriching follow-up questions. For instance:

“Are you still struggling with Zayn’s departure from 1D?”

“How did the meeting with your boss go?”

“Did you like the pork dumplings we got from that Chinese place last week, and should I bring some over later?”


A bad question reveals your laziness and inability to listen or possibly to care about anyone other than yourself, at all. For example:

“What’s your story?”

“So, tell me about yourself.”

“Okay, your turn.”

Notice that two of those weren’t even questions, but rather demands. I know part of this is a macho thing—it’s a lot more commanding to use tell me about X rather than can you tell me a little more about X—but it’s the 21st century, and most of us are fed up with the macho thing by now. Other people don’t exist to entertain you with their mouth sounds, and they’re not gonna tell you anything if you’ve already made it clearly you don’t really care. A conversation is not one dominant party instructing a subordinate to fill in blanks like they’re applying for a job. Nor is it two people exchanging boring, broad monologues. It requires actually responding to the other person, by listening and not merely waiting for your turn to talk.


That reminds me. No monologues. If you are an exceptional storyteller, you can tell one great story in a night. Maybe two. But odds are, you are not an exceptional storyteller. You are someone who likes talking aimlessly about yourself a lot more than anyone else likes listening. If you are a good storyteller, you will see a) genuine rapt interest in the eyes of whomever is listening, and/or b) them gasping for breath during their extreme laughter at your intentional punch lines. Conversely, if they are staring at their food, nodding on autopilot, glancing around the room, or checking their phone, your tale is not going over well. Fortunately, you know what to do to rescue the moment: Ask a question.

Don’t be an ass. Don’t play devil’s advocate unless you’re doing it in a sensitive and non-combative way for someone who you know will appreciate it; never, ever play devil’s advocate when you don’t even know what perspective you might be trying to share, and you just want an excuse to irritate someone and act like a dick.


If someone is describing a specific problem to you, she may or may not want your advice. One way for you to know is to wait for her to throw out a What do you think? or So I wanted to get your opinion. If they don’t ask, she might not want it. It’s quite common for attempts at problem-solving to come out as criticism, blame, or sheer insensitivity; she may just want you to listen. If you’re really dying to weigh in, venture one comment and see how it’s received. If the other person acts irritated or confused by what you said, that’s a very clear cue not to proceed with five more suggestions. Many a conversation has spiraled out of control—and many a relationship has been damaged—because one person is uncomfortable with another person’s pain or anxiety.

Incidentally, this—turning to someone for emotional support—is perhaps the one situation where a monologue is allowed. If you are in distress, those close to you will forgive your explaining the bad situation and expressing your resulting stress. But it’s not something you should unleash on acquaintances.


Listen. I mean, you gotta. Why else are you on this earth? You cannot ask good questions without listening and observing and learning about what another person cares about. You cannot have a good conversation without good questions. So you see, listening is the foundation for the whole damn carnival ride. Now go forth with open ears and a judicious mouth, and conversate the world into a warmer, happier place.

Charlotte Shane is a writer living in New York and tweeting from @charoshane. Also, her TinyLetter is famous among those who love emotions and long emails.


Illustration by Tara Jacoby.

Adequate Man is Deadspin’s new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.