Questions to Ask During Speed Dating
Short questions built for a four or five minute round, when you have time for two of them and one follow-up. Chosen to hear how someone talks rather than to collect facts you could read on a profile. The groups run from openers through funny questions to ask at speed dating when a round needs a laugh, and on to closers for the last half minute. One group is for seniors: speed dating questions to ask a woman or a man at an over-fifties night, where there is more life behind every answer.
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The questions
Each question, and why to ask it
Openers
What made you come tonight?
Why ask it
Answers run from being dragged along by a friend to deciding to stop waiting for something to happen. Either is fine, and what you actually learn is whether they can be candid with a stranger in the first thirty seconds.
How is it going so far, honestly?
Why ask it
The word honestly gives permission to say something other than "great". People who can laugh about an awkward format are usually easier company than people determined to perform.
What do you do with your Saturdays?
Why ask it
Better than asking about hobbies, which invites a list. This gets the actual shape of a free day, and whether it is spent alone, outdoors, or with the same four people every week.
What is the last thing you got completely absorbed in?
Why ask it
You are looking for the change in how they talk when they hit something they care about. The subject matters far less than whether that shift happens at all.
Are you a planner, or a decide-at-the-door person?
Why ask it
A small compatibility question that predicts a lot of low-level friction later. Most people know their answer instantly, and the ones who claim to be both are usually the planner.
What is your read on this format?
Why ask it
Turns the two of you into observers of the same odd situation, which is the fastest way to feel like allies. It also shows how they handle talking about the thing everyone is politely ignoring.
Is this your first one of these?
Why ask it
Small piece of information, large payoff. Veterans have a script and will run it; first-timers are nervous and usually relieved if you go first, so the answer tells you how much of the round you should carry.
What would you be doing tonight if you were not here?
Why ask it
A pleasant way to find out what their default evening is, which is more informative than what their ideal evening would be. It also has a natural warmth to it, since you are both here rather than there.
Are you from here, or did you choose to live here?
Why ask it
Two very different stories and both are easy to tell. People who chose a city will tell you why, which is more revealing in four minutes than a list of hobbies, and people who grew up there usually have opinions about it.
About them
What do your friends come to you for?
Why ask it
It gets a description of their role in a group without asking them to describe their personality. Nobody has ever answered this with something they are not at least a bit proud of.
What is the best thing within walking distance of your place?
Why ask it
Concrete, easy, and it tells you where they live and how they use it. It also surfaces whether they know their neighbourhood or just sleep there.
What is taking up most of your attention at the moment?
Why ask it
A gentler route into work, family or study than asking what they do. What they name first is a fair indication of what a relationship would be competing with.
What do you wish people asked you instead of what you do for work?
Why ask it
Hands them the chance to steer, which is a relief for anyone whose job is dull to explain. Watch whether they use the opening or hand it straight back.
What is something you tried recently for the first time?
Why ask it
Recency is what makes this work: everyone has a story from years ago. Nothing in the last year usually means life is full of obligations, which is worth knowing without judging.
Are you close to your family?
Why ask it
Heavier than the rest, so it needs a warm tone and an easy exit. Both a yes and a no can be perfectly healthy answers; what tells you something is how comfortable they are giving one.
What is something people get wrong about you at first?
Why ask it
Invites self-knowledge without inviting a confession. Answers that are secretly compliments, being told they seem intimidating, tell you as much as the sincere ones.
What do you do for a living, and is it what you expected to end up doing?
Why ask it
Most people answer the first half in four words and skip the second. The ones who engage with the second half tell you how they handle detours, which is far more useful than a job title.
What could you talk about for an hour without preparing?
Why ask it
Invites enthusiasm without demanding a passion, which is a word that makes people freeze. If they name something, ask a follow-up immediately, because watching someone light up is the actual information you came for.
What have you been doing too much of lately?
Why ask it
A sideways route into how someone spends their time, and it gets past the curated hobby answer. Expect something small and true, such as too much work or one specific television series, and notice whether they can laugh about it.
What's a place you've been that you'd go back to tomorrow?
Why ask it
A specific place with a reason attached shows how they travel: for the food, for the quiet, for the people. "Anywhere warm" usually means they have not thought about it, which is fine to know in four minutes.
What's the most spontaneous thing you've done, and did it work out?
Why ask it
The second half carries the weight. Anyone can tell a story about a last-minute trip. How they describe the part that went wrong shows whether they take responsibility or hand it to circumstances.
Do you cook? What do you actually make on a normal Tuesday?
Why ask it
The follow-up is the point: everyone says they cook, and the honest answers are pasta, eggs, or nothing. It is also the first question of the night with a chance of turning into an actual plan.
Big group person or two friends and a quiet pub?
Why ask it
A two-option question fits the clock and produces a fast, honest answer about social energy. Mismatches on this rarely resolve later, so it is worth knowing in minute two rather than on date three.
What are you bad at and no longer trying to fix?
Why ask it
Self-deprecation with a limit on it, which is why it works better than asking about weaknesses. An answer with real acceptance in it is a good sign; a humblebrag about working too hard is a fairly reliable bad one.
What is the most recent thing you changed your mind about?
Why ask it
Reveals whether someone updates. A concrete answer, however small, suggests they can be argued with pleasantly, and being unable to think of anything at all is worth noticing in someone you might disagree with later.
Who's the first person you call when something good happens?
Why ask it
One sentence maps their inner circle: a sibling, a school friend, a parent. Someone who says they do not really call anyone is also answering, and it is worth hearing how they say it.
What's a small thing that reliably makes your day better?
Why ask it
Small and concrete is the requirement. A specific walk, decent coffee, ten minutes with the door shut. The answer shows whether they can look after themselves without needing a vacation to do it.
What are you working towards at the moment?
Why ask it
Deliberately broad so it covers a qualification, a house, a marathon, or nothing in particular. The scale of the answer, and whether they seem to enjoy the pursuit, says more than the goal itself.
Funny
Is there a food you would defend in an argument?
Why ask it
Deliberately light, and it works because it gives permission to have a strong opinion about nothing. People who cannot commit to a view here often will not commit to one on anything in five minutes.
What is the last thing that made you laugh out loud?
Why ask it
You learn their sense of humour by example rather than by adjective. A specific answer beats "lots of things", which is what people say when they cannot remember the last time.
What's the strangest thing you know a lot about?
Why ask it
Odd expertise is where a person stops sounding like a profile: canal locks, the offside rule, one family recipe nobody else can make. Answers here are memorable, which matters when they are comparing a dozen conversations at the end of the night.
What's your most-played song at the moment, and are you embarrassed by it?
Why ask it
Naming a current favourite is instant and specific, and the embarrassment half shows how much they curate their taste for an audience. It also leaves you something to send afterward if there is an afterward.
What did you want to be when you were ten?
Why ask it
Light, fast, and almost impossible to answer in a boring way. It also lets someone talk about work obliquely if they want to, which is a relief for anyone whose job is hard to explain or who would rather not lead with it.
What are you weirdly good at?
Why ask it
Invites a specific story instead of a resume, and it rewards self-awareness. People who deflect entirely here often deflect elsewhere too, while people who overclaim tend to keep talking past the point where you stopped asking.
What do you and your friends argue about?
Why ask it
Unusual enough to get a genuine laugh, and it shows you how they handle disagreement in the telling. Someone who says they never argue with anyone is describing either a very calm life or a habit of avoidance.
What's something everyone else seems to enjoy that you can't stand?
Why ask it
An unpopular opinion is more informative than a popular one, and offering it to a stranger takes a little nerve. How they disagree with the room is a preview of how they will disagree with you.
What's a hill you'd die on that doesn't matter at all?
Why ask it
Trivial fierceness is funny and safe, and it shows their arguing style, playful or genuinely rigid, in under a minute. How they defend the position tells you more than the position does.
What's the worst date story you're willing to tell a stranger?
Why ask it
Almost everyone in the room has one, and inviting it sets a tone of candour without asking anything private. Listen for whether the story is about a ridiculous situation or entirely about how badly the other person behaved.
What is the worst opening line you have heard tonight?
Why ask it
Best from the third round on, when there is material. It moves you from one more candidate to the person they are comparing notes with, and if the answer turns out to be yours, laugh first.
What would your friends bet on you saying in the first minute of every round?
Why ask it
Asks for their own catchphrase, which people usually know and rather enjoy admitting. If it then slips out before the bell, you both get the joke for free.
What is the least impressive fact about you?
Why ask it
Everyone has spent the evening leading with their best material, so asking for the opposite gets a laugh and a truer picture. Trade one of your own straight afterwards, or it lands as a test.
What is the oddest thing in your bag or pockets right now?
Why ask it
The evidence is on the table within seconds, and a bit of show and tell breaks up a night of nothing but talking. A loyalty card for a café that shut years ago counts as a strong answer.
If tonight were a film, what would it be called?
Why ask it
Summing up the evening as a joke is easier than summing it up sincerely, and you hear the honest verdict anyway. A disaster movie and a romantic comedy are both good signs, since either means they are enjoying the absurdity.
What they want
What does a good first date look like to you?
Why ask it
Practical, and it doubles as an invitation without being one. A specific answer means they have thought about what they enjoy; "anything, really" often means they are used to going along with whatever is suggested.
What is a green flag you notice early?
Why ask it
People describe what they value more clearly through what reassures them than through a list of qualities they want. The answer often turns out to be something they do themselves.
What are you definitely not looking for?
Why ask it
The polite way to reach dealbreakers in a few minutes, and most people answer it directly. If the whole answer is a description of one ex, they may still be in that story.
Where do you want to be living in a few years?
Why ask it
One of the few genuine compatibility facts you can establish in four minutes. Answers about another country or moving back home are worth hearing before you get attached to the evening.
Do you usually know within five minutes whether you like someone?
Why ask it
Asking about snap judgements is fair in a format built entirely on them, and it invites honesty about how the evening is going. It also opens the door to saying you would like to see them again.
What makes you want to see someone again after a few minutes?
Why ask it
Slightly meta and works well near the end of a round, when you have both relaxed. The answer tends to be about manner rather than looks, and it tells you what they are paying attention to during these conversations.
What are you hoping to find here that you are not finding on the apps?
Why ask it
Invites a genuinely candid answer because everyone in the room has the same complaint. Listen for whether they describe what they want or only what they resent, since the second answer tends to follow people into relationships.
What is something you would want someone to know early rather than late?
Why ask it
Direct, and most people appreciate being asked. Answers range from practical facts about children or relocation to how much time alone they need. Any of those would take three dates to surface otherwise.
How long do you usually text someone before you suggest actually meeting up?
Why ask it
This gives you their pace outright: some people message for weeks, others want a date by Friday. Mismatched pace ends more promising starts than any lack of chemistry.
Seniors
What does a good week look like for you these days?
Why ask it
Kinder than asking whether someone has retired, since plenty of people at a seniors' night still work, volunteer or mind grandchildren three days a week. You hear how full the calendar already is, and where a new person might fit.
What music was playing when you were twenty?
Why ask it
One song title brings back a whole decade, and within seconds the two of you know whether you shared a dance floor era. Keep it for a round where the talk has been polite and flat.
What do you do now that you would never have done at forty?
Why ask it
It makes age the interesting part of the conversation instead of the thing everyone steps around. Travelling alone, or saying no without an excuse, are the kinds of answer that show how someone has changed.
Who do you spend most of your time with these days?
Why ask it
Family, old friends, a dog and nobody much are all honest answers, and children or grandchildren can come into it as much or as little as the person likes. It is a gentler route to hearing whether they live alone than asking outright.
Are you hoping for company, a travel partner, or something more?
Why ask it
At a seniors' event the range is wide, from someone to go to the theatre with to a second marriage, and nobody enjoys guessing. Three options make it easy for a woman or a man you met two minutes ago to answer plainly.
Is there a trip or a project you have been saving for the right company?
Why ask it
This one looks forward, which matters in a room where much of the small talk looks back. A named place or plan tells you what they still want, and whether you would enjoy being the company.
What do you know about a good partnership now that you did not know at thirty?
Why ask it
Many people at seniors' speed dating have a long relationship behind them, ended by divorce or by a death, and this lets them draw on it without telling the story. Take a short answer as a complete one and do not press.
Closers
If we run out of time, what should I write down so I remember you?
Why ask it
A closer that ends the round warmly and solves the real problem of twelve near-identical conversations. What they choose is often the thing they most want to be known for.
Of everyone you've talked to tonight, what's the best question you've been asked?
Why ask it
Late in the evening this is more welcome than another fresh topic, and it produces a real answer plus a laugh about the format. Whichever question they name is usually the one they were hoping to be asked.
Is there anything you want to ask me before the bell goes?
Why ask it
The most efficient question in speed dating, because whether they have one ready tells you if they were curious or just answering. The question they choose also tells you what they were quietly wondering the whole time.
If we swapped numbers, what would you suggest doing?
Why ask it
Turns vague interest into something concrete while you are still sitting there, and it separates people who want to see you again from people who are being polite. A specific plan is a yes, drinks sometime is usually a no.
Making a four-minute round work
Practical guidance for the conversation itself
Inside the round
Two questions, one follow-up
Four minutes fits roughly two exchanges done properly. Rattling through six questions turns the table into an interview and neither of you remembers any of it afterwards.
Answer your own question first if they stall
Going first takes the pressure off and shows what depth of answer you were hoping for. Keep your version to about fifteen seconds.
Let the follow-up be specific
Repeat one detail they gave and ask about that. It is the clearest signal that you were listening rather than waiting for your turn.
One funny question, then a straight one
A funny question buys a laugh and half a minute of ease, but two in a row starts to sound like a routine. Follow the laugh with something from the About them group while you are both relaxed.
At a seniors' speed dating night
Ask about now and next more than about the past. A divorce, or a late husband or wife, is theirs to raise, and a woman who has been asked about her grandchildren at every table may be glad of a question about herself.
Between rounds
- Write one specific line per person right after the bell, not at the end of the night
- Note what you would want to ask them next, which is a better yes-or-no test than a rating
- Rotate your opening question rather than repeating the same one twelve times, or your delivery goes flat
- Drink water between rounds; most people talk far more than they expect to
- Expect two or three rounds to be genuinely awkward, and do not read that as your night going badly
What tends to go wrong
Interviewing instead of talking
Firing off questions without offering anything back makes people close up. Aim for something close to an even split of talking.
Going straight to the heavy questions
Past relationships, money and family history in the first minute mostly produce polite deflection. Save them for a longer conversation later.
Rehearsing the same answers all night
By round eight your own answers stop sounding like you. Change which story you tell to keep the conversation live for yourself.
Deciding in the first thirty seconds
Nervousness reads as coldness, and quiet rooms suit some people badly. Reserve judgement until after the second question.