57 First Date Questions That Spark Real Conversation

Questions do not make people fall in love, whatever the headline on the famous study said. What they produce is closeness, and the mechanism is a ramp, so a question one step above where the conversation has got to gets answered, while a question four steps above gets a polite deflection. These 57 are grouped by purpose, and no one should lean on more than half a dozen in an evening, which most lists never mention.

The Case Against Working Through a List

The strongest objection comes from the people who see the most first dates. Matchmakers report that the complaint they hear most the day after is that the evening felt like a job interview, question after question, with no room left for anything to develop between the questions.

Skipping straight to the deep material is off-putting in a way unrelated to the questions themselves. Announce that you have no interest in small talk and start in on the serious ones, and the person across the table registers not bad questions but a missing step, because the two of you have not got there yet, and what has been skipped is ceremony.

There is something real behind that objection. Small talk has a job. It is a low-risk way for two people to find out if there is anything worth climbing toward, and either one can leave having lost nothing. Delete it, and you have removed the search while keeping the expectation of finding something.

So the honest position on skipping small talk is narrower than the phrase suggests. What is worth skipping is the stalling kind, the weather and the weekend plans, which are what a conversation reaches for once it has run out of material. The warm-up itself stays.

Two things follow from that. A bank of 57 questions is something to draw from and never something to work through, and volume is not the variable in any case.

The second is that the fear of going deeper is calibrated wrong, and that has been measured. Strangers put into a deep conversation, asked to describe a time they had cried in front of another person or what they were most grateful for, expected it to be far more awkward than it turned out to be. People given both a shallow and a deep conversation predicted they would prefer the shallow one and afterward preferred the deep one. What gets underestimated is how interested the other person is in going there.

The Tests of a Good Question

An interview prompt asks for a fact that is already stored. Where did you grow up retrieves an answer somebody has given 200 times. What did your street sound like on a summer night makes them go and look, and the pause before that answer is what you are asking for.

A good question also leaves an obvious next question hanging, because the benefit of asking questions lies almost entirely in follow-ups. Across hundreds of conversations with strangers, asking more opening questions changed nothing measurable. Asking more follow-ups changed the outcome. Among speed daters, those who asked more follow-up questions were more likely to get a yes to a second date. So the value of any entry in a bank like this is the number of good follow-ups it makes available.

The remaining tests are about symmetry. A question whose answer you are silently scoring stops the disclosure it was meant to start. A question you would not answer yourself in the next 30 seconds is an interrogation. And a question a single notch above where the conversation stands will be answered, while one that leaps several notches ahead comes across as a stunt.

The ramp is the mechanism. In the original research, pairs of strangers worked through increasingly personal questions in three timed sets. They reported measurably greater closeness than a control group that made ordinary small talk for the same 45 minutes. The effect, from the inside, is not noticing you have entered intimate territory until you are already there. What that procedure produced was a felt sense of connection. It did not produce love, and the headline that made it famous belongs to a journalist who tried it.

Questions for the First Half of the Evening

The four groups here work in the first hour, when neither of you has earned anything yet. They are personal without being heavy, which is the combination people miss when they try to jump ahead. Each one can be answered in a sentence by somebody who does not want to go further, and opened up for ten minutes by somebody who does.

Openers Beyond Small Talk

Use these in the first 15 minutes, in place of what do you do and how was the traffic. Each asks about the present, which keeps the answer current and brief, and each gives you an obvious next step. If one comes back flat, nothing has been lost.

• What has been taking up more of your head than it deserves lately?
• What part of your week do you look forward to?
• What did you almost do tonight instead of this?
• What is the last thing that made you laugh out loud on your own?
• What do people usually get wrong about you when they first meet you?
• What is the last thing you looked up out of pure curiosity?
• What have you changed your mind about in the last year?
• What is a topic you could talk about for an hour with no warning?

Enthusiasms and Passions

This is the fastest route to somebody becoming animated, and animation is portable. You do not need to share the interest at all. Asking how something is done gets you the enthusiasm attached to it, which is the part you are there for.

• What is something you love that you rarely get to talk about?
• What is the nerdiest thing you know a lot about?
• What is the last thing you learned that made you want to tell someone?
• What kind of problem do you enjoy solving?
• What is a song, book, or film you keep returning to, and what does it do for you?
• What were you obsessed with growing up and have never let go of?
• What is the best thing anyone has recommended to you in the last year?

Questions for a Scene

These ask for a scene with a beginning and an end, something a person has to build in the moment. They work best in the second half of the first hour, once there is enough comfort for somebody to take 3 minutes instead of 3 sentences. Answer with one of your own afterward, and the evening starts trading stories.

• What is the most out-of-character thing you have ever done?
• Tell me about a time you got lost, and it turned out fine.
• What is the strangest place you have ever fallen asleep?
• What is a story your friends make you tell?
• What is the closest you have come to giving up on something you then finished?
• What is the best evening you have had in the last year, start to finish?
• What is the most nervous you have ever been before something that turned out fine?

Opinions With Low Stakes

Mild disagreement is one of the more enjoyable things two people can do on a first evening, provided nothing depends on the outcome. These invite a position without requiring agreement, and they reveal a surprising amount, since what someone finds overrated can be revealing. Keep them playful.

• What is a popular thing you have never understood the appeal of?
• What is something everyone seems to hate that you secretly like?
• What is an opinion of yours that most of your friends disagree with?
• What is the most overrated piece of advice people give?
• What would you make compulsory if you could?
• What is a hill you will die on that does not matter at all?
• Would you rather be excellent at one thing or decent at 10?

Questions for Later, Once the Evening Is Going Well

Nothing in this half belongs in the first 30 minutes. Use these once the conversation has already gone somewhere on its own, one at a time, with your own answer alongside. Disclosure runs both ways, or it does not run, and somebody who only asks never triggers the half of the effect where opening up makes you like the person you opened up to.

Growing Up and Formative Years

The first genuinely personal group, and the safest of the later ones, because childhood is far enough away to be discussed without much exposure. It also explains a great deal about the adult across the table. Ask one, answer it yourself, and let the follow-ups do the work.

• What did you want to be when you were eight?
• What is something from your childhood you would want to give a kid today?
• Who was the adult who took an interest in you?
• What is something you believed as a kid that took you far too long to unlearn?
• What is a piece of advice you were given early that turned out to be wrong?
• What did you have to teach yourself because nobody taught you?
• What is something about where you grew up that outsiders never understand?

Values and Priorities

Asking what somebody makes of their own life is the move in this group. The are-you-glad-you-did-it kind of question gets you a long way in a single answer, and none of these require anybody to be impressive to answer them well.

• What do you value most in a friendship?
• When you have a hard decision to make, who do you talk to first?
• Are you glad you took the path you took, or do you wonder about the other one?
• What have you become less tolerant of as you have matured?
• How do you know when you trust someone?
• What does a good week look like for you, honestly?
• What is a mistake you are glad you made?

Closeness and Connection

This group asks about closeness in general terms, which is why it can be brought up on the first evening without putting anything about the two of you on the table. Two of them come almost word-for-word from the closeness procedure. They sound like ordinary curiosity, and they are doing considerably more than that.

• What does friendship mean to you?
• What role do love and affection play in your life?
• How do you know when someone is looking after you?
• What is the kindest thing anyone has done for you that they probably do not remember?
• Who knows you best, and what do they know that other people miss?
• How do you like to be disagreed with?
• What is something you need after a bad day?

Deeper Questions for a Good Evening

Use one of these at a time, and only where the evening has earned it. Every one produces a real answer, which is exactly why a run of them turns into an interrogation. Keep the last one in your pocket, since asking what has surprised somebody about tonight puts the two of you in the same evening rather than in separate histories.

• What is your most treasured memory?
• Is there something you have dreamed of doing for years, and what has stopped you?
• What in your life are you most grateful for?
• What is something you would want someone to know about you early instead of late?
• What, if anything, is too serious to be joked about?
• What is something you are still working out about yourself? - What has surprised you about tonight?

How to Follow Up on Any of These

A question is worth roughly what you do with the answer, and the follow-ups are the technique. None of them require preparation.

• What made you pick that one?
• When did that start?
• What was that like at the time, as opposed to now?
• Who else knows that about you?
• Say more about that part.
• Is that still true?
• What part of that story do people usually get wrong?

Then answer it yourself before you ask anything else. Most people skip that half, and it is what makes them good company.

Two failure modes deserve watching. The first is asking a question, listening to the answer, then immediately turning the conversation back to yourself, which announces that the answer was never the point. The second is bouncing the identical question straight back. It is the easiest thing to reach for when you do not know what to say next, which is why people keep doing it right through a conversation, and it moves nothing forward for either of you.

A short skip list, since not every question earns its place. Nothing that scores somebody’s circumstances, because that turns an evening into an assessment. Nothing built like a complaint, since worst-date and dating-app questions are complaints wearing a question mark. Nothing about why the last relationship ended. And nothing you would not answer yourself inside 30 seconds, which is the test that catches everything the other three miss.

57 questions are a supply. An evening needs at most six of them, and the six that work will be the ones you did not plan.