Questions to Ask When Speed Dating
Twenty questions built for a four to seven minute round, ordered from easy openers to the ones that tell you whether you want a second conversation. Each one is short enough to ask across a noisy table and open enough that the answer is not one word.
The questions
Open any question for the note
Is this your first time doing one of these?
Why ask it
A throwaway opener that does real work: it settles nerves and tells you whether they are treating tonight as an experiment or as a search. Veterans usually have an opinion about the format, and that opinion is often the first honest thing they say.
What made you decide to come tonight?
Why ask it
Answers land in three piles: curiosity, a friend dragged them, or they actually want to meet someone. Only the third group is planning a second date. Someone who cannot name a reason has usually not decided they want to be dating yet.
What do you do with your time when you are not working?
Why ask it
Better than asking what they do, because it skips the job title recital and gets to how their week is actually spent. Listen for whether they name anything at all, since people who go blank here often have very little unstructured life to share with someone.
What is something you did recently that you would happily do again this weekend?
Why ask it
This is a compatibility question disguised as small talk, because the answer is effectively a date suggestion. If everything they name requires no one else present, that is worth noticing early rather than in month three.
What is the last thing you got properly obsessed with?
Why ask it
You are looking for the change in energy, not the topic. Someone who lights up about tide charts or a video game is showing you what enthusiasm looks like on them, and whether it is something you would enjoy sitting next to.
Are you more of a plan-it-out person or a decide-at-the-door person?
Why ask it
One of the most reliable sources of friction between couples, and people answer it honestly because neither answer sounds bad. The revealing part is how they describe the other type, which tells you how they handle someone unlike them.
What is your neighborhood like, and would you stay?
Why ask it
Doubles as a logistics check without asking where they live. Someone planning to move cities in six months will often mention it here, which is information you would rather have now than after you are attached.
What is a small thing that reliably ruins your day?
Why ask it
The scale of the answer tells you more than the content. Loud chewing is a quirk, being kept waiting four minutes is a temperament, and a five minute account of a grievance with a coworker is a preview.
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 did you want to be when you were ten?
Why ask it
Nearly everyone has an answer and it makes people laugh, which is worth a lot in minute three. The follow-up worth listening for is whether they say anything about how that turned into what they do now.
Who do you call first when something good happens?
Why ask it
A quiet way to see the shape of their close relationships: a parent, a sibling, a best friend of fifteen years, or nobody in particular. Hesitation is not a red flag on its own, but it usually means the honest answer is complicated.
What is the best thing you have eaten in this city?
Why ask it
Low stakes, high specificity, and it gives you a concrete second-date idea if the round goes well. It also surfaces whether they go out at all, and whether they are the sort of person who has opinions or defers to yours.
What kind of trip do you actually enjoy: a full itinerary, a beach, or a city you have never seen?
Why ask it
More useful than asking where they would go, because it is about how they like to spend unstructured time with another person. Anyone who answers all three has not traveled with someone whose preference differs from theirs.
What are you working on outside of your job?
Why ask it
Reveals what they do without being paid or watched, which is usually closer to who they are. A blank answer is not disqualifying, but paired with a job they dislike it often means their whole week is spent waiting for the weekend.
What have you changed your mind about in the last couple of years?
Why ask it
The searching question of the set, and worth saving for the back half. You are testing whether their views can move at all. Answers about small tastes are pleasant, answers about how they treat people are the ones that matter.
How do you usually spend a Sunday?
Why ask it
The most honest question about daily rhythm, because Sunday is unclaimed time. Early riser and slow starter is a real friction point, and so is a Sunday that is entirely booked with other people you would be joining.
What is something you would want a date to know about you early rather than late?
Why ask it
Gives permission to volunteer the thing that usually comes out on date four: a demanding job, kids, a recent breakup, a plan to relocate. How gracefully they handle the invitation matters as much as the disclosure.
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.
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.
Working a Speed Dating Round
Practical guidance for the conversation itself
How to Spend Four Minutes
Spend the first thirty seconds on nothing
Names, how the night is going, whether the room is too loud. Trying to be interesting immediately reads as a pitch, and the person opposite is nervous too. The point of the first half minute is to sound like a person, not to gather information.
Ask two questions, not twelve
A round that covers two topics properly is remembered; a round that covers ten feels like an intake form. Pick one light question and one from the back half of this list, then follow the answers wherever they go.
Answer your own question before they ask
Give a short version of your own answer after theirs. It turns an interview into a conversation and it gives them something to grab onto, which is what makes people tick your name on the card.
Write one word on the card between rounds
By round eight everyone blurs. One concrete detail, tide charts, sourdough, moving to Lisbon, is worth more than a rating out of ten, and it gives you an opening line if you match.
What to Notice While They Talk
- Whether they ask you anything unprompted, which is the single strongest signal in the format
- Whether their stories have other people in them, or only themselves
- How they talk about an ex, a boss, or a friend when the topic arrives uninvited
- Whether they answer the question you asked or the one they had prepared
- How they handle being interrupted by the bell, which is a small test of grace
- Whether you were performing the whole time, because that usually means you were not enjoying it
Questions to Leave Alone
- Why their last relationship ended, which cannot be answered well in four minutes
- What they earn, what their rent is, or anything that sounds like screening
- Marriage and children timelines, which are worth discussing later and read as an ultimatum now
- Anything that requires them to defend a political or religious position to a stranger
- The riddle or brain teaser you like, which makes the round about you
- A question you would not answer yourself if they asked it back
After the Bell
Decide on the conversation, not the resume
Whether four minutes went quickly is better data than whether their job, height, or interests match your list. People routinely tick the impressive stranger they were bored by and skip the one they laughed with.
Message with a detail, not a greeting
Referring to the specific thing they said proves you were listening and gets a reply far more often than a hello. This is why the one word on the card matters.
Expect a low match rate and do not read into it
Mutual matches are usually a small fraction of the people you sat with, because both sides have to tick the same name. That is the shape of the format rather than a verdict on how the night went for you.