Questions to Ask Speed Dating
Twenty questions for a speed dating night, written for the point where you have said the same three things eleven times and want a round worth remembering. Each one is quick to answer and hard to answer blandly, ordered from an easy opener to the end of the round.
The questions
Open any question for the note
What made you say yes to tonight instead of another evening at home?
Why ask it
Reasons for turning up vary wildly: a birthday, a bet, a break-up, a deliberate plan to meet someone. It is a gentler version of asking what they want, and it opens the round on something concrete.
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'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'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.
Who's the most interesting person you've met this year?
Why ask it
You learn who they notice and admire, and whether they meet anybody new at all. A blank here often points to a very closed week-to-week life, which is worth knowing early.
What do you spend money on that other people think is a waste?
Why ask it
This is a plain window onto priorities without asking about salary or savings. Answers range from books to horses to always taking a taxi home, and each one describes a different life.
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 last thing you learned to do badly?
Why ask it
Willingness to be bad at something new says a lot about how they handle discomfort. If they cannot name anything, they may only be doing what they already do well.
What have you quit that you're glad you quit?
Why ask it
Quitting well is underrated, whether it was a job, a course, a habit, or a relationship. Notice whether they can describe the decision without needing you to confirm it was the right one.
What's the nicest thing a stranger has ever done for you?
Why ask it
The answer shows what registers with them as kindness and how much they expect from other people. Small stories, a held door, a paid fare, tend to reveal more than a dramatic one.
What's the last thing you cancelled plans for?
Why ask it
Whatever outranks an existing commitment is a direct statement of priorities, whether that is a sibling, a deadline, or a nap. If everything gets cancelled for work, you have your answer about the next few months.
What does an ideal Friday night look like for you at this point in your life?
Why ask it
The last clause is doing the work. Most people's honest answer shifts over the decades, and naming the present tense gets you a realistic picture rather than an aspirational one.
Would you rather always be twenty minutes early or twenty minutes late?
Why ask it
A trivial question that governs a surprising amount of shared logistics. Two people who answer differently will negotiate it every week for as long as they know each other.
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.
What would your last flatmate say about you?
Why ask it
Third-person questions get past self-presentation, because repeating someone else's complaint is easier than volunteering a fault. Whether the answer comes out affectionate or defensive is the part to notice.
What's a compliment you get that you don't quite believe?
Why ask it
The compliment someone cannot accept usually marks something tender, and asking it lightly is more disarming than asking about insecurities. Total deflection tells you how much they let people in.
What are you better at than you were a year ago?
Why ask it
A modest, checkable question that rewards anyone actually working at something. Broad self-improvement language with no specific example is a mild warning sign.
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.
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.
Getting through a whole speed dating night
Practical guidance for the conversation itself
Before you go
- Check the format: number of rounds, minutes per round, whether it is seated rotation or a mingling event. It changes how much you can say and how much you should plan.
- Find out how matches work. Some events use paper cards, some an app, and some only pass on details when both people tick each other.
- Eat first. Three hours of talking on an empty stomach is the real reason people run out of energy by round eight.
- Pick three questions you actually want the answers to, and leave the rest of the night unscripted.
- Decide in advance what you will say when someone asks what you are looking for. Improvising that answer at speed rarely goes well.
Pacing yourself across the rounds
The first two rounds are always the worst, and the people you meet in them get an unfairly bad version of you. Assume that, and do not write anyone off on the basis of round one either, since they are warming up as well. By the middle of the evening you will notice yourself running a script, at which point deliberately ask something you have not asked all night. The last rounds suffer from fatigue rather than nerves: keep them shorter in your own head, ask one question, listen properly, and stop trying to be impressive.
Keeping track
- 1Write on the card while they are still walking away, not at the end of the night.
- 2Note one distinguishing detail and one feeling: "climbs, easy to talk to" is enough.
- 3Mark a maybe as a maybe rather than a yes. Cards filled in generously produce matches you cannot remember agreeing to.
- 4Add a question you wish you had asked. If you match, it is your first message.
- 5Look at your cards the next morning before you confirm anything, not at midnight.
Etiquette that makes the night better
- Ask their name again if you lose it. Everyone loses several, and pretending is more awkward than asking.
- Give roughly half the airtime away. Rounds where one person talks throughout are remembered as bad conversations regardless of content.
- Do not rank the other guests out loud. It travels, and small rooms are smaller than they look.
- End on a clear note. "That was fun, I hope you get a good match" is a kind way to close a round that is not going anywhere.
- If you are enjoying it, say so before the bell rather than hoping they infer it from your card.
Afterward
Following up
Message within a day or two and refer to something specific from your conversation. Anything generic reads as a copy sent to several people, which at a speed dating event it often is.
Suggesting the second meeting
Propose something short and specific: a coffee or a drink with a natural end. It matches the pace of how you met and lowers the cost for both of you.
No matches
A blank night is common and says little. The pool at any one event is a few dozen people on one evening, which is too small a sample to conclude anything about yourself.
Staying safe
Meet in public, tell a friend where you are going, and arrange your own way home. Organisers are used to being asked how they handle guests who behave badly, and a good one will answer plainly.