First date questions: 50 good, deep and fun ones to ask

Updated October 5, 2026 · 10 min read

Fifty first date questions in five groups of ten, each with a line on why that kind of question works. The research points less at the question than at the follow-up. Also covered: what the 36 questions study found, where the studies stop, and four questions to skip.

This is a list to pick from, not a script. Nobody wants fifty questions over one drink. For where to ask them, see our first date ideas.

Why the question matters less than the follow-up

We looked at several popular lists of questions to ask on a first date, including Wondermind’s. Most run to dozens of questions in tidy groups, and few say why any of them should work. The best evidence we found points somewhere else. In a 2017 series of studies, people told to ask more questions were liked more and rated as more responsive, and follow-up questions were the kind most tied to the effect. In 368 coded transcripts of 15-minute text chats, follow-ups made up 40.5% of all questions (Huang et al., 2017).

A speed-dating study in the same paper covered 110 participants and 1,961 four-minute dates. The average date had 9.8 questions, 4.5 of them follow-ups. Speed daters who asked more follow-up questions were more likely to get a yes to a second date, a modest link that did not hold in every analysis. The total number of questions was at best weakly related, and that link did not hold once the asker’s own appeal was controlled for (Huang et al., 2017). The speed-dating result is correlational. It shows a link and cannot show a cause.

The other finding is about what people get wrong on either side of a conversation. Beforehand, they expect it to go worse than it does. A mini meta-analysis of seven studies with 2,304 participants found that people’s fears before talking to a stranger were larger than the experience turned out to be (Sandstrom & Boothby, 2021). Afterward, people underestimate how much the other person liked them, which researchers call the liking gap (Boothby et al., 2018). If that holds on a first date, the date probably went better than the walk home suggests. Our first date tips page covers how to read a date afterward.

50 questions to ask on a first date

Five groups of ten, numbered straight through. Each group comes with one line on why that kind of question works, and where that comes from. Three or four questions from different groups is plenty for one evening.

Easy openers that leave a thread

Why this works: an opener only matters if the answer gives you something to follow up on, and follow-ups are the part the research ties to being liked (Huang et al., 2017).

1. How did you end up living in your neighborhood?
2. What did you do today before this?
3. Have you been here before, or is this new for you too?
4. What’s taking up most of your week right now?
5. What’s something around here you’ve been meaning to try?
6. What’s the last thing you got way too into for a few weeks?
7. Who do you text the most, and is it mostly memes?
8. What’s the last thing you recommended to someone?
9. What did you think was a real job when you were ten?
10. What’s the part of your week you’d never give up?

Specific stories

Why this works: a story comes with details, and every detail is a follow-up waiting to happen (Huang et al., 2017). Our reasoning from there: concrete first, abstract later.

11. What’s the last thing that made you laugh somewhere you really shouldn’t have?
12. What’s the best meal you’ve had this year, and where was it?
13. What’s the worst trip you’ve ever been on?
14. When was the last time you changed your mind about something?
15. What’s the nicest thing a stranger has ever done for you?
16. What’s a skill you picked up that surprised people?
17. What’s the last thing you were proud of that nobody else noticed?
18. What’s the strangest job you’ve ever had?
19. What’s the last thing you bought that turned out to be completely worth it?
20. What’s a family tradition that sounds odd when you explain it out loud?

Funny and hypothetical

Why this works: in one study of first meetings, using humor went with more liking and closeness (Treger et al., 2013). We read the abstract only, so treat that as a pointer rather than a measured effect.

21. What’s a hill you’d die on that doesn’t matter at all?
22. If you could be instantly great at one useless skill, what would it be?
23. Which fictional place would you actually move to?
24. What’s your most controversial food opinion?
25. If your friends wrote your dating profile, what would they get wrong?
26. What’s the dumbest way you’ve ever hurt yourself?
27. If you had to compete in the Olympics tomorrow, which event gives you the best shot?
28. What would your walk-up song be?
29. What’s a trend you were completely wrong about?
30. If you had to swap lives with someone in this room for a day, who’s your pick?

What matters to you, with a little depth

Why this works: in a series of experiments, strangers who had deeper conversations felt less awkward and more connected than they had expected, and underestimated how much the other person cared about what they shared (Kardas et al., 2022). The participants were strangers, and a first date is not far off that.

31. What’s something you believe now that you didn’t five years ago?
32. Who’s had the biggest say in how you spend your time?
33. What’s something you work on that nobody pays you for?
34. What does a really good Sunday look like for you?
35. What’s a small thing that makes you trust someone?
36. What did your family get right?
37. What’s something you’re bad at and have no plans to fix?
38. When did you last lose track of time?
39. What’s a hard decision you’re glad you made?
40. What do your closest friends come to you for?

Questions you answer too

Why this works: a meta-analysis found that people who disclose more are liked more, that people disclose more to those they like, and that people like others more after disclosing to them (Collins & Miller, 1994). We read the abstract, not the full paper. A 2013 study title says what its authors found: reciprocal self-disclosure, taking turns, promoted liking (Sprecher et al., 2013).

Our answers are placeholders. Swap in your own, or the question gets strange.

41. I’d say brunch is the most overrated meal there is. What would you pick?
42. For me, a cabin with no Wi-Fi beats a beach resort. Which one are you?
43. My worst habit is sending voice memos nobody asked for. What’s yours?
44. I’m a morning person who pretends not to be. Which are you?
45. Nineteen is the age I’d go back to, for one summer only. Which would you pick?
46. The best advice I ever got was “just send the email.” What’s yours?
47. I’m on time for everything except things I’m excited about. How about you?
48. My free Saturdays go to flea markets. Where do yours go?
49. The thing I’m weirdly good at is parallel parking. What’s yours?
50. The best show I’ve ever seen was in a room smaller than this one. What’s yours?

What to talk about on a first date

Whatever the other person gives you a thread on. The five groups above are starting points, and the research on this page points at what happens after the opener: in the speed-dating data, follow-up questions were weakly linked to a yes for a second date, while the total number of questions was at best weakly related (Huang et al., 2017). So the topic that works is the one they just raised.

If you want a shortlist anyway, ours: how their week actually went, one thing they are looking forward to, a place they keep going back to, and whatever they said in the app that made you reply. Our view: skip the interview topics (job title, apartment, exes) until they come up on their own, and let silence sit for a breath before you reach for the next question. A date is not a quiz, and the person who asks nothing back is telling you something too.

Four questions to skip

These are the questions that show up on most avoid-lists we looked at. We agree with three of them outright and have a view on the fourth.

Anything that sounds like a job interview. “Where do you see yourself in five years?” and “What do you do for fun?” are the classics. They are not rude. They ask for a summary, and summaries are hard to follow up on.

Questions about exes. “Why did your last relationship end?” asks for a story that is sad, long or unflattering to somebody, often all three. It also hands the evening to a person who is not there.

“Why are you single?” There is no good answer to it, only defensive ones.

“What are you looking for?” before the second date. Our view: on a first date the question tends to get a rehearsed answer, and the honest one is often “I’ll know after tonight.” Not everyone agrees. One widely read list, by Alyssa Mancao for Wondermind, puts intentions and intimacy on the first date (Mancao, 2025). If you need the answer early, asking is reasonable.

What the 36 questions actually were

The “36 questions to fall in love” come from a 1997 paper by Arthur Aron and colleagues. It was a 45-minute lab procedure. Assigned pairs took turns with questions that moved from light to personal, so the self-disclosure escalated as they went. Afterward, those pairs reported more closeness than pairs given small-talk tasks (Aron et al., 1997).

That is what it measured: closeness, not attraction and not love. In follow-up studies, whether the pair had matching attitudes, or expected to be liked, made no measurable difference (Aron et al., 1997). Aron himself has said the long-term effects are unknown, and the often-repeated story of a couple from the study who married, he told triple j, involved research assistants who piloted the questions, not participants (triple j, 2017).

Nothing stops you from borrowing a few. The early ones sit fine on a first date. The later ones were built for a lab with 45 minutes on the clock, and some read heavy across a small table. Spread over several dates, they suit slow dating, the habit of taking longer at each step on purpose.

How to use this

1. A follow-up before the next question. “Wait, why Ohio?” counts. Follow-ups are the part the research ties to being liked (Huang et al., 2017). Jumping straight to a new topic is what gives a date the interview feel.
2. Your own answer to your own question. The disclosure research runs both ways: people like those who share and share more with those they like (Collins & Miller, 1994). If you ask about the worst trip, yours is probably coming up next.
3. A pause that sits. After a deeper answer, a few seconds of quiet is not a failure. People expect deeper conversations with strangers to feel more awkward than they turn out to (Kardas et al., 2022). We would guess the same holds for a pause.
4. A gloomier read than theirs. After a conversation, people tend to underestimate how much the other person liked them (Boothby et al., 2018). Both of you are probably underrating how it went.
5. A list that gets put away. It is for the opening stretch. Once you are both talking without it, it has done its job. If the date goes well, what comes next has a name: the talking stage.