Dating · Dates and first texts
What to talk about on a first date
Start with the place and the moment, then light things she enjoys: what she's into lately, her free Saturdays, a place she'd go back to, food. Trade one small opinion. Then go one step toward something real, like what she's proud of this year, and give your own answer first. Follow what she lights up about, not your list. Keep exes, money and wedding timelines for later.
What to talk about in the first ten minutes
Talk about where you are: the menu, the line, the music, how you each got there. It's in front of you both, so neither of you has to perform yet.
Friday night, a taco place Joanna picked, with a line out the door. The usual opener is "So, what do you do?" She says pharmacist, six years, and waits. Fair, but in minute one it asks for a summary, and summaries end in a period. The place does better: "You picked this place, so I'm trusting you. What do I order?" The al pastor, she says, and go easy on the green salsa. Her sister found it the week Joanna moved to town. One question about tacos, and you've met her sister.
The job question isn't off limits; just don't stay on it. When she says "pharmacist," skip "Which pharmacy?" and go past the label, to what she enjoys.
Conversation starters that go somewhere
The light topics that work point at what she likes, not at facts. "Where did you grow up?" closes after one answer; a good Saturday has a story behind it. Four that rarely fail:
- What she's into lately: "What's taking up your evenings these days?"
- A free Saturday: "What does a good Saturday look like, with nothing planned?"
- A place she'd go back to: "Where would you go back to tomorrow if you could?"
- Food and small pleasures: "What's the best thing you've eaten this month?"
Answer your own question too, in a sentence or two, so it isn't an interview and she can see how much to say. Walking to get ice cream, you tell Anjali: "My best Saturday is a long breakfast and a bike ride with no plan. I always end up in a thrift store I didn't mean to go into. What's yours?" Hers ends at a used bookstore, with a nap she refuses to apologize for.
Then one small opinion, on something with no right answer: "What do you make of people who clap when the plane lands?" She's firmly for it. Say where you stand in a sentence, and ask what makes her think so. One is enough; five in a row is a quiz.
How to go deeper without it feeling like an interview
Think of the date as a ladder: the place, then what she enjoys, then one small opinion, then one real thing, like what she's proud of this year or what she's trying to learn. One rung at a time, with your answer first.
At a wine bar, you tell Corinne: "I'm trying to learn to cook one dinner well this year. Right now it's risotto, and the risotto is winning. What are you trying to get better at?" She tells you about her Tuesday Spanish class: she wants to talk with her grandmother without her mom translating. From risotto to her grandmother in one step.
She sets the pace. If she answers lightly and moves on, stay light; one offer is enough. If she goes further on her own, go with her. A personal question can carry an out, said easily: "You can skip this one: what made you move here?" If she skips it, leave it.
The order matters. Pairs of strangers who spent 45 minutes on questions that grew gradually more personal felt closer than pairs given small talk (Aron et al., 1997), and a later study found the same (Sprecher, 2021). And in a series of experiments, deeper talks between strangers felt less awkward and left people more connected than they had predicted, partly because they underestimated how much the other person would care about what they shared (Kardas, Kumar & Epley, 2022).
A scene to try
Your first date with Sadie is a tour of the old lighthouse on the point, and for a minute you have the lamp room to yourselves. She looks out at the water and says, "I walk the beach for sea glass most mornings before work. It's kind of sad, really." What do you say?
One way to handle it
"Sad how? I'd like to hear about those mornings, if you feel like telling it."
Why it works
- It takes her own word, "sad," and asks what it means to her: one step past the sea glass, not a dive.
- It's one question, said lightly. Not "Sad how? Are you lonely? What's missing?"
- "If you feel like telling it" is a real out: she can take the step or wave it off, so the pace stays hers.
In the app, the lesson "One Step Deeper, With an Out" ends with a scene like this one: you type or say your own line, and the AI tells you what landed and what to change.
How to not run out of things to say
Follow the thread she picks, not the list in your head. The list is for when the talk stalls. While it's moving, the next topic is usually something she just said in passing.
At an arcade bar, Bridget is losing at skee-ball and laughing about it: "…and I had better aim on the ship, in a storm." "Travel" is next on your list. Skip it: "Wait. What ship?" She sang on a cruise ship for two seasons, and the rest of the game is about the night the band played through a storm.
Some topics just die. You ask about her work, and the answers shrink to two words while she lines up her next shot. Don't try a gentler version of the same question. Go back to a thread that was alive: "Okay, I need more about the ship. Did you ever get seasick on stage?"
What not to talk about on a first date
Some topics are fine by the fifth date and heavy on the first. Keep these for later:
- Exes. Yours brings a third person to the table; asking about hers asks her to review her past for a near stranger.
- Money. Her job, yes. Her salary, rent or debts, no.
- Therapy-speak. "What's your attachment style?" turns dinner into an intake form.
- Kids and marriage timelines. On date one, "Do you want kids?" makes it a screening. If it's a dealbreaker for you, it can wait until you both know you want more dates.
- Heavy politics, unless it clearly matters to you both. If she volunteers for a campaign and brings it up, ask: it's her thing, not a debate.
That's courtesy, not a study. If she raises one of these herself, follow her, kindly. Over coffee, Heather mentions she moved here after a breakup. Don't dig, and don't trade breakup stories. "That's a big move. How are you liking it here?" lets her say more if she wants, and talk about the city if she doesn't.
The last ten minutes
Don't open a new topic now. Do two things.
Say what you enjoyed, once, and name it: "I liked how you told the storm story. You were back on that stage." A specific line tells her you were there. People tend to hold these back: in a series of experiments, people giving sincere compliments underestimated how good the other person would feel and overestimated how awkward it would be (Zhao & Epley, 2021).
Then, if you'd like another date, ask once and plainly, tied to tonight: "You said there's a karaoke place you've been meaning to try. Want to go next Friday? If not, no hard feelings." A "maybe" with no day in it gets one easy "Sure, no problem," and nothing more.
Try it today
Two reps, with anyone you talk to today.
- The next time someone hands you a label, a job or a hometown, ask one question past it: what's taking up their evenings lately. Give your own answer in a sentence.
- At the end of one conversation, name one specific thing you enjoyed about it, once: "I liked hearing about…" Afterward, note how they took it.
Practice this in the app
Dating Conversations
Two lessons on exactly this, "One Step Deeper, With an Out" and "Your Turn, Same Depth": the one question that takes a light topic somewhere real, and the piece of your own you give before you ask. 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.
New subscribers get the first 7 days of the yearly plan free. The subscription renews automatically until you cancel it in your store settings.
Questions people ask
How do I not get nervous on a first date?
Going on a first date and I hate awkward silence. How do I avoid it?
What do I talk about with a girl I really like?
Sources checked
- Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: a procedure and some preliminary findings. Personality and Social Psychology Bulletin. doi:10.1177/0146167297234003
- Sprecher, S. (2021). Closeness and other affiliative outcomes generated from the Fast Friends procedure: a comparison with a small-talk task and unstructured self-disclosure and the moderating role of mode of communication. Journal of Social and Personal Relationships. doi:10.1177/0265407521996055
- Kardas, M., Kumar, A., & Epley, N. (2022). Overly shallow?: miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology. doi:10.1037/pspa0000281
- Zhao, X., & Epley, N. (2021). Insufficiently complimentary?: underestimating the positive impact of compliments creates a barrier to expressing them. Journal of Personality and Social Psychology. doi:10.1037/pspa0000277