Questions to Ask on Speed Dating
Speed dating gives you roughly four minutes per person. These twenty questions are short enough to ask and answer in that time, and pointed enough to tell you whether you want a longer conversation later.
The questions
Open any question for the note
What made you decide to try speed dating?
Why ask it
Honest answers run from "a friend dragged me here" to "I gave up on the apps." Either is fine. What you are watching is whether they can field a slightly awkward question without getting defensive or over-explaining.
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.
Where did you grow up, and does it still feel like home?
Why ask it
The second half is what makes it worth asking. People who left somewhere deliberately usually say why in one sentence, and people who still drive back every month are telling you where their weekends and holidays already go.
What's the last thing that made you laugh out loud?
Why ask it
Asking for the last thing rather than the funniest thing blocks the rehearsed anecdote. If nothing from the past week comes to mind, that gap is itself worth noticing.
What's something you could talk about for an hour without getting bored?
Why ask it
This finds enthusiasm without asking anyone to label it. The answer is usually unglamorous: fantasy leagues, tiling, medieval sieges. Watch how long they stay on it before checking whether you are still interested.
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.
Are you a planner, or do you decide things at the last minute?
Why ask it
The answer predicts how a first date with them would actually run: who picks the place, how far ahead it gets booked, how they react when the booking falls through.
What are you better at than most people you know?
Why ask it
Phrased this way it gives permission to brag without it feeling like bragging, and the skill is often oddly specific: parallel parking, remembering names, staying calm on hold with an insurance company.
What have you picked up recently, a hobby, a class, something you got hooked on?
Why ask it
Recent beats favorite. What someone took up in the last few months shows what they currently have time and energy for, which reads their life more accurately than a hobby they list out of habit.
What does a good weekend look like for you?
Why ask it
Listen for the shape rather than the activities: how much is solo, how much is booked in advance, how much is spent recovering from the week. Two people can both say "quiet weekend" and mean opposite things.
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.
Do you see yourself staying in this city?
Why ask it
Worth asking before the bell rings because it can settle compatibility fast. A person with a plan to move across the country in eighteen months and a person closing on a house here are describing different next chapters.
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 do people get wrong about you when they first meet you?
Why ask it
You get their self-awareness and a preview of how they think they land. People who answer "that I'm standoffish" or "that I'm agreeable" almost always keep going, and the explanation is the useful part.
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.
What's something you've changed your mind about in the last few years?
Why ask it
This separates people who hold opinions from people who examine them. "Nothing really" is a real answer. Anything counts, from a political position to how they handle a difficult relative.
What would you like to be doing more of a year from now?
Why ask it
Softer than asking about goals, and it gets a straighter answer because it asks for a direction rather than a plan. Notice whether anyone else features in the picture they describe.
What are you actually hoping to find at one of these events?
Why ask it
Late in a round this cuts through the pleasantries. Some people want a relationship, some want an evening out of the house, some genuinely have not decided. Knowing which spares you both the guessing afterward.
What's the best advice you've taken, not just heard?
Why ask it
The words "not just heard" filter out the fridge-magnet answers. What comes back instead is usually a moment when someone changed course because of something another person said to them.
What's a question you wish people asked you instead of "what do you do?"
Why ask it
A good closer, because it hands them the wheel and lets them raise whatever they wanted to talk about for the last four minutes. It also shows what they are tired of being reduced to.
How to use these questions in a four-minute round
Practical guidance for the conversation itself
Before the first bell
- Pick three questions you will ask everyone, so you have a baseline to compare answers against, then improvise from there.
- Decide in advance what would rule someone out for you. Location, wanting kids, and how they treat staff are the three that most often decide it and the three people forget to check.
- Eat something first. Most events run two hours with a bar and no food, and hunger reads as boredom.
- Write the name down the moment you sit, along with one word you would not otherwise remember. By round eight everyone blurs.
How to spend the four minutes
- 1First thirty seconds: names, and something about the room or the event. This is not wasted time, it settles both of you.
- 2Next ninety seconds: one open question and a genuine follow-up to their answer. One question well followed beats three asked coldly.
- 3Next ninety seconds: let them ask you something, and answer it properly rather than deflecting back immediately.
- 4Last thirty seconds: one thing you would want to pick up again later. That is what you will write on the card, and what you will mention if you match.
Between rounds
- Score on curiosity, not performance. Some of the best matches are quiet in a loud room with a stranger and a timer.
- Note one concrete detail per person, "restoring a motorbike", "moving to Denver in spring". Ratings without details are useless the next morning.
- Do not adjust your notes to match how attractive you found someone. Write what happened, decide later.
What goes wrong
Interviewing instead of talking
Firing off six questions in four minutes feels productive and lands as an interrogation. Two questions and two follow-ups will give you more, and will leave them feeling like they were listened to rather than screened.
Saving the real questions for later
There is no later. If whether they want to stay in the city matters to you, ask in round one, not on a second date three weeks in.
Filling every silence
A two-second pause after their answer often produces the most honest sentence of the round. Speed dating trains people to talk over the gap. Resist it.
Heavy topics in a loud room
Bereavement, divorce settlements, and health scares are not off-limits for life, but a shouted four-minute version does neither of you any favors. If someone raises one, acknowledge it plainly and let them decide how far to go.