Questions to Ask in Speed Dating
Questions built for four-minute speed dating rounds, short enough to say out loud and specific enough to get an answer that is not the one they have already given six times.
The questions
Open any question for the note
What made you decide to come tonight?
Why ask it
Better than the weather and better than asking what they do, because everyone has an answer and the answers differ. A friend dragged them, they moved here recently, they decided to stop using apps: each one gives you somewhere to go next.
How has your day been, honestly?
Why ask it
The word honestly does the work. It gives permission to skip the automatic 'fine' and say the train was awful or that they nearly cancelled, which is the first genuine exchange of the evening for both of you.
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.
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 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 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 is the last thing you got completely absorbed in?
Why ask it
Asks for a recent, specific instance rather than a general interest, so you get a book, a repair project, or a rabbit hole from last Tuesday. Answers that reach back ten years usually mean life is currently full of obligations.
What does a good Saturday look like for you?
Why ask it
This is a compatibility question disguised as small talk, because it exposes energy levels rather than tastes. Someone whose good Saturday starts at six in the morning and someone whose good Saturday starts at two are describing different lives.
Are you a planner, or do you decide on the day?
Why ask it
Quick to answer and genuinely predictive of how a first date would feel. Watch whether they say it with amusement or apology, since the second suggests they have been criticised for it and it may be a sore point.
Who did you last properly laugh with, and what was it about?
Why ask it
The second half is what makes this work. You learn who is close to them and what their humour actually is, which no amount of asking about a sense of humour will ever produce.
What do your friends come to you for?
Why ask it
People describe themselves generously, but they describe their role among friends accurately, because it is based on evidence. Help with moving, advice about work, or being the one who organises everything are three very different people.
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.
What does your week look like when nothing is going wrong?
Why ask it
A practical question about rhythm rather than ambition. Shift work, constant travel, or three evenings of commitments are the things that quietly determine whether dating someone is workable, and they rarely come up until date three.
What have you stopped doing that you used to love?
Why ask it
Slightly wistful and often the most memorable exchange of the round. The answer is usually a casualty of time or money rather than lost interest, and how they talk about it tells you how they handle compromise.
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.
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.
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.
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.
Is there anything you wish people asked you at these things?
Why ask it
Hands them the last thirty seconds and often produces the line you remember afterwards. It also implicitly acknowledges the format, which almost always gets a laugh and lowers the temperature.
Working Within Four-Minute Rounds
Practical guidance for the conversation itself
How to Spend the Time
Two questions per round, not eight
Four minutes holds roughly two questions with real follow-ups, or eight with none. The rounds people remember are the ones that went somewhere, so ask, listen, and follow the thread rather than working through a list.
Skip the job question, at least at first
Everyone will have asked it, the answer is rehearsed by round three, and for many people it is the least interesting fact about them. If it matters to you, it will come out anyway once they are talking about their week.
Take notes between rounds, not during
After twelve conversations, faces and answers detach from each other completely. One or two words on the card the moment they walk away, ideally something they said rather than how they looked, is what makes your later choices deliberate.
Answer your own question too
Asking without offering anything turns the round into an interview and people close up. Give a short version of your own answer first or immediately after, and keep it short, because the round belongs to both of you.
What Kills a Round
Asking about past relationships
Four minutes is nowhere near enough context for this, and it puts the other person in an unwinnable position: guarded sounds evasive, candid sounds bitter. Whatever you learn will be misleading anyway.
Running an interrogation
A rapid sequence of questions with no reaction in between feels like a screening call. If you notice yourself asking the next one before they have finished the last answer, slow down and respond to what they said instead.
Recycling the same script all night
By the eighth round your delivery flattens and people can hear it. Vary which questions you open with, partly to stay interested yourself, partly because the fourth person can tell they are getting a routine.
Deciding in the first thirty seconds
Nerves make people seem duller than they are, and confidence makes them seem better matched than they are. Give each round its full length before you write anything on the card.