First date questions

Questions that get a first date past the interview stage

For two

First dates fail at the same place: work, city, weekend plans, and then a pause nobody knows how to fill. The fix is not being bolder, it is asking about something specific enough to answer. These cards do that. None of them require a confession, and all of them are hard to answer in one word.

How to play

  1. Take turns, one card each, and answer your own card too
  2. Ask one follow-up about a detail from the answer
  3. Skip anything that feels like too much, out loud and without apologising
  4. Stop while it is still going well, that is the whole trick

The cards

Warm-up

The first twenty minutes, before anything heavier

  1. What is the best thing that happened to you this week?
  2. Which place in this city never gets old for you?
  3. What are you good at and never mention?
  4. What can you talk about for an hour with no preparation?
  5. What do you cook best?
  6. What lives in your bag for no reason at all?
  7. Which film do you rewatch the most?
  8. What did you spend far too much time on last month?
  9. Which everyday thing do you enjoy more than you should?
  10. What is the last thing you looked up out of pure curiosity?
  11. Where do you go when you need twenty minutes to yourself?
  12. What do you order when you cannot decide?
  13. Which season suits you best, and why that one?
  14. What is the most useless thing you know a lot about?
  15. Which app do you open without meaning to?
  16. What did you plan for this week and quietly skip?
  17. Which sound do you find weirdly satisfying?
  18. What do you always keep in the fridge?
  19. Which city would you live in for a month, just to try?
  20. What is your idea of a well spent Sunday?

Deeper

Still safe, but they need a real answer

  1. What was your plan for life at sixteen?
  2. Which of your own decisions do you consider brave?
  3. What do people rarely ask you about, though you would happily talk about it?
  4. What is your favourite memory from childhood?
  5. What comes easily to you that others seem to struggle with?
  6. Which of your traits have you finally made peace with?
  7. What tells you an evening went well?
  8. What would you like to know about me?
  9. What are you working on that has nothing to do with money?
  10. Which advice did you ignore and later wish you had not?
  11. What changed your mind in the last few years?
  12. What do you want more of in the next year?
  13. Which risk turned out to be worth it?
  14. What do you find hard to say out loud, in general?
  15. Who taught you something you still use daily?
  16. What do you want people to notice about you first?
  17. Which habit are you actually proud of?
  18. What did you get wrong about adult life?
  19. What are you curious about right now?
  20. What would a good year look like for you?

Funny

To break a pause without making it heavier

  1. Which of your habits gives you away before you speak?
  2. What do you remember from childhood in suspicious detail?
  3. Where would you go tomorrow if no visa existed?
  4. What would a good second meeting look like?
  5. What is the worst haircut you have ever had?
  6. Which trend did you follow and now deny?
  7. What is the most ridiculous thing you own?
  8. Which fictional character would find you insufferable?
  9. What would your autobiography be called?
  10. What is the pettiest reason you have judged someone?
  11. Which skill do you fake convincingly?
  12. What would you be terrible at professionally?
  13. Which compliment do you never know how to take?
  14. What is the most useless purchase you defend?
  15. Which small thing annoys you far more than it should?
  16. What would people be surprised to learn you enjoy?
  17. Which lie do you tell to get out of plans?
  18. What is your most irrational fear?
  19. Which animal would you be, according to your friends?
  20. What would you take on stage if you had to perform tonight?

Advice

  1. Do not run the list, three cards across an evening is plenty, the rest of the time you are just talking
  2. Answer first yourself, a question you have already answered stops sounding like an interview
  3. Follow the detail, not the topic, the interesting part is usually the small thing they mentioned in passing

Questions about this set

Is this not too much for a first date?

None of these ask about exes, money or plans together. The heaviest one asks which of your own decisions you consider brave.

What if they refuse to answer?

Then you learned something and you move to the next card. A refusal is not a failed date, it is a boundary, and noticing it early is useful.

Can I use these over text before we meet?

You can, but they are built for a table. In writing the follow-up gets lost, and the follow-up is where the answer actually is.

Other question sets