First date questions

The hard part of a first date is not finding something to say, it is finding something to say that does not sound like a job interview. A question you both answer is different from a question one of you asks: it gives you somewhere to go next, and it lets either of you be the interesting one.

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Why a game beats a list of questions

A list makes one of you the interviewer. You ask, they answer, you think of the next one while they are still talking, and forty minutes later you know their job history and nothing about them.

A game removes the asymmetry. The phone asks, you both answer, and neither of you is responsible for keeping the conversation alive. That is a surprisingly large amount of pressure to take off a first date.

It also gives you a graceful exit. Putting the phone down is easy and needs no explanation, whereas abandoning a conversation you started yourself feels like a verdict on the person opposite you.

What to ask, and what to leave

The questions here are Would You Rather dilemmas rather than direct questions, which matters more than it sounds. Asking someone what they value invites a rehearsed answer. Asking them to choose between two specific inconveniences gets you a real one, and usually a reason attached to it.

Nothing here asks about exes, salary, family difficulty or anything you would not want to answer on a first meeting yourself. That is not squeamishness — those questions produce a careful answer rather than an honest one, so they fail on their own terms.

If a question does land somewhere interesting, abandon the game. The cards exist to start conversations, not to be completed. Getting through eight of them because you spent twenty minutes on the third is the best possible outcome.

Practical notes for a real date

It works across a table, and it works better than it sounds on a video call, where silences are more obvious and there is no shared environment to comment on.

Keep it to ten cards or fewer. This is a way into a conversation, not the evening itself, and a table where two people are still staring at a phone after an hour has gone wrong somewhere.

Set the intensity low. The gentle end is genuinely safe with someone you met an hour ago, and you can move it up on a second date if there is one. Nothing in the free set is explicit at any setting, but bold questions still land differently with a stranger than with a partner of four years.

20 Would You Rather questions

1.Would you rather always know what time it is without checking — or — always know exactly how long something will take
2.Would you rather never have to queue for anything again — or — never have to fill in a form again
3.Would you rather be able to cook any dish perfectly — or — never need to cook and always eat well
4.Would you rather have a photographic memory for names — or — have one for everything you have ever read
5.Would you rather live somewhere it is always slightly too warm — or — live somewhere it is always slightly too cold
6.Would you rather be excellent at one instrument — or — be passable at six of them
7.Would you rather always get the window seat — or — always get through security in one minute
8.Would you rather read every book you have been meaning to — or — watch every film you have been meaning to
9.Would you rather have an extra hour every morning — or — have an extra hour every evening
10.Would you rather never lose anything again — or — never be late for anything again
11.Would you rather understand every language but speak only one — or — speak three fluently and understand no others
12.Would you rather have a job with a long commute you enjoy — or — have one two minutes away that you tolerate
13.Would you rather live by the sea and rarely go in — or — live by mountains and rarely climb them
14.Would you rather always have the perfect thing to say afterwards — or — always have something adequate to say at the time
15.Would you rather be given a free flight anywhere once a year — or — be given a free week off whenever you ask
16.Would you rather sleep perfectly for six hours — or — sleep badly for nine
17.Would you rather have every meal out be excellent but expensive — or — have every meal in be cheap and pretty good
18.Would you rather be the funniest person in every room — or — be the one everyone finds easiest to talk to
19.Would you rather always know the right amount to tip — or — always know what a taxi should have cost
20.Would you rather fall asleep anywhere within five minutes — or — never feel tired before midnight

Play with the full set

These are a sample. The game has the rest — no signup needed.

Play Would You Rather

Common questions

Is playing a question game on a first date awkward?

Less awkward than the alternative, in practice. Both of you know the first twenty minutes are the difficult part, and a phone that supplies the questions is a shared prop rather than an admission that neither of you can think of anything. Introduce it as something to try for ten minutes and it lands fine.

What if we disagree on an answer?

That is the useful outcome. Would You Rather is built so both options cost something, so a disagreement tells you what each of you weighs more heavily. Agreeing on everything is pleasant and tells you almost nothing.

Can we use this before we meet, over text?

Yes. Share the link and you both get the same questions in the same order, which works over a call or a chat. It is a better opener than asking how their week was, and it gives you something to refer back to when you do meet.