First date questions

Twenty cards that get 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

  1. What brought you here tonight, besides the app?
  2. Which place in this city do you show people you like?
  3. What are you good at and never mention?
  4. Which of your habits gives you away before you speak?
  5. What can you talk about for an hour with no preparation?
  6. What was your plan for life at sixteen?
  7. What do you choose when you are tired and nobody is watching?
  8. Which of your own decisions do you consider brave?
  9. What puts you off a person quickly?
  10. Which question are you tired of hearing on dates?
  11. Where would you go tomorrow if no visa existed?
  12. What do you remember from childhood in suspicious detail?
  13. What do you cook when you want to impress someone?
  14. What lives in your bag for no reason at all?
  15. Which film do you rewatch and not admit to?
  16. What comes easily to you that others seem to struggle with?
  17. Which of your traits have you finally made peace with?
  18. What tells you an evening went well?
  19. What would you ask me if it did not feel too early?
  20. What would a good second meeting look like?

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