How to not be boring on a date

Why dates get boring

Thursday night, a brewery patio, a first date with Erin. "So what do you do?" She tells you, asks back, and you tell her. Where you each grew up. One brother, two sisters. Forty minutes in, you've traded everything you'd put on a form, and neither of you has said one thing the other could push on, laugh at or ask about. It was nice, and forgettable.

The topics weren't the problem. Facts are finished: "I'm an accountant" leads only to the next fact, and a run of questions turns into a job interview with drinks. What makes a date interesting sits between the facts: what you think, what happened to you, how you react to her, and whether there's any play. Each fix below swaps a fact for something she can pick up.

Have an opinion, and let her disagree

"Yeah, totally" to everything she likes feels safe, and it reads as nobody home. A small opinion gives her something to meet: low stakes, said with some conviction and a smile, open to argument.

Waiting on your order at a Detroit-style pizza place, you say, "The corner piece is the whole reason this pizza exists." Priya laughs. "I always give the corners away." Now there's something to talk about.

Then let her disagree, and enjoy it. When she offers a take you don't share, push back with a grin instead of folding or trying to win. She says pineapple is the best topping, and you say, "That's a strong take on pineapple pizza. Make your case." You're arguing with the take, not with her, and asking to hear more. If her case is good, say so: "Okay, sweet and salty. I'll give you that." Losing a pizza argument out loud is half the fun. Small means small: a topping, not a politician.

Tell one story, with one odd detail

When she asks what you do, the boring answer is the job description, and the worse one is ten minutes of it. Give her the job in one line, then one story with one detail she can see.

"I repair elevators. Last month the first person to ride one I'd just fixed was a man holding a three-tier wedding cake, alone, sweating." That's the whole story. She'll ask about the cake or tell you about the elevator she got stuck in, and you're talking.

"Work's been crazy" gives her nothing to picture; a sweating man with a wedding cake gives her a picture and a question. Pick the detail that holds the feeling, say it, and stop: no explaining why it was funny, no second story. If she tells one of hers, hear it to the end.

React out loud, then ask what's behind it

Half of being interesting is being interested where she can hear it. At the bowling alley, waiting for your lane, Lauren mentions she drove an ice cream truck one summer. "Oh, cool" files it. "Wait. The truck with the song?" tells her it landed, and she admits she still hears the song in her sleep.

Then ask the question behind the fact: facts have reasons, and the reasons are where she is. She says she teaches fourth grade. "How long have you been doing that?" gets a number. "What made you pick fourth grade? That's a very specific age" gets a story: the year she subbed in every grade, and fourth graders were the only ones who argued back.

Recordings of speed dates point the same way. The dates that ended with a sense of connection were the ones where the woman was engaged and at the center of the conversation, and the man showed he was following and understanding her (McFarland, Jurafsky & Rawlings, 2013). Your opinions and stories give her something to play with; your reactions show her she's heard.

How to be playful without being mean

Play turns a pleasant date into a fun one, and it doesn't take prepared jokes. Most of it is small:

• Laugh when she's funny, out loud, then add a line. When a joke doesn't land for you, skip the fake laugh: "That one went right past me. Walk me through it."
• Play along with her bit. She says the rental shoes make you look like extras in a seventies movie. Take it as true and add one line: "Then we're the extras who win the bowling scene."
• Tease the situation, not her. On a first date, tease the menu, the wait, the lane that eats your ball, or a take she offered, never her looks, her job or anything she seems touchy about. Exaggeration shows it's play: "A forty-minute wait for brunch. We'll be different people by the time we eat."

Right after a tease, watch her face. A laugh and a comeback mean keep going. A "ha" with no smile means it stung: "Sorry, that came out meaner than I meant it," a new subject, and no more teasing tonight. "Relax, I'm joking" makes it worse. And skip rehearsed lines: an opener you memorized could be said to anyone, and she can tell.

You don't have to be a comedian. In two studies of strangers getting acquainted, humor went with liking and closeness, by way of enjoying the talk and feeling liked back (Treger, Sprecher & Erber, 2013). And when a man and a woman who had just met talked for about ten minutes, both people's interest in a date went with laughing at the same moment (Hall, 2015). Count the laughs you share, not the jokes you land.

Be where you are: the place, the phone, the pause

The easiest material is the place you're both in. Notice what's a little off and say it in one line. At mini golf: "This windmill has been ruining dates since 1985." She can answer without thinking, which is the point.

Put your phone in your pocket on silent, or at least face down. In two experiments, people who messaged during a face-to-face conversation came across as less polite and attentive, and picking up the phone on their own looked worse than answering a notification. Their partners also rated the conversation lower, though they didn't like the phone users any less (Vanden Abeele, Antheunis & Schouten, 2016). On a date, one glance at the screen tells her she's the second most interesting thing at the table.

And when it goes quiet for a second, let it. After she answers something real, a one-second pause often brings out the best part, the thing she adds when she sees you're still listening. Filling every gap with "So, any siblings?" sends you back to the form. If the quiet runs longer, here's how to handle awkward silence.

Try it today

Two reps, with whoever you talk to today.

• In one conversation, say one small opinion out loud: a food, a seat, the right way to do something. When the other person disagrees, ask them to make their case instead of folding.
• The next time someone tells you a fact about themselves, a job, a move, a hobby, ask what's behind it: "What made you pick that?" Afterward, note whether you got a number or a story.

Practice this in the app

Flirting & Chemistry

Two lessons on exactly this, "Flirt Your Own Way" and "Tease a Trifle, Then Check": one line of your own about the moment instead of a stock line, and the light tease that stays kind because you watch her face right after. Each ends with a scene you answer in your own words and one line to use the same day. The quiz builds your path first; your first course is free, with AI feedback included.

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Questions people ask

Sources checked

1. McFarland, D. A., Jurafsky, D., & Rawlings, C. M. (2013). Making the connection: social bonding in courtship situations. American Journal of Sociology. doi:10.1086/670240
2. Treger, S., Sprecher, S., & Erber, R. (2013). Laughing and liking: exploring the interpersonal effects of humor use in initial social interactions. European Journal of Social Psychology. doi:10.1002/ejsp.1962
3. Hall, J. A. (2015). Sexual selection and humor in courtship: a case for warmth and extroversion. Evolutionary Psychology. doi:10.1177/1474704915598918
4. Vanden Abeele, M. M. P., Antheunis, M. L., & Schouten, A. P. (2016). The effect of mobile messaging during a conversation on impression formation and interaction quality. Computers in Human Behavior. doi:10.1016/j.chb.2016.04.005

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