32 date night questions

A date night does not need forty questions, it needs the right one at the right point in the evening. These are arranged in the order you would actually use them: light at the start, better in the middle, warmer at the end.

Questions for the start of the night

Light, quick, and designed to get you both talking before the food arrives.

1. What was the best part of your week that had nothing to do with work?
2. What have you been looking forward to?
3. What is something small that made you happy today?
4. What did you almost do this week and did not?
5. What have you been thinking about a lot lately?
6. What is the last thing that genuinely surprised you?
7. What would you do with tomorrow if it were free?
8. What is something you want to do again soon?
9. What is the best thing you have eaten recently?
10. What is something you are looking forward to that is months away?

Questions for the middle of the night

Once you have both relaxed, these get somewhere more interesting.

11. What do you think you are better at than you were a year ago?
12. What is something you have changed your mind about recently?
13. What do you wish you had more time for?
14. What is a thing you would try if you knew you would not be bad at it?
15. What do you think you will remember about this year?
16. What is a decision you are glad you made?
17. What is something you find harder than people realise?
18. What is a habit you would like to break?
19. What would you do with a completely free month?
20. What is something you want to be true in five years?
21. What is the best advice you have ever ignored?
22. What is a compliment you never forgot?

Questions for the end of the night

Warmer, and better once the plates are cleared.

23. When did you last feel really close to me?
24. What is something I do that you have never mentioned but like?
25. What do you need more of from me at the moment?
26. What is your favourite ordinary thing we do together?
27. What is a night out or in that you still think about?
28. What would make next week easier for you?
29. What is something you would like us to do more often?
30. What do you think we are best at as a pair?
31. What is something you would like to plan together?
32. What do you want tonight to be like?

Frequently asked questions

What should we talk about on date night?

Start with the present rather than the day. "What have you been looking forward to?" gets a better answer than "how was your day?", because the second one has been asked too many times to mean anything.

How do you avoid running out of things to say?

Usually you have not run out of topics, only new information, which happens when the week was ordinary. Ask about what changed their mind, what they almost did, or what they keep meaning to do.

What are good questions for a first date versus a long relationship?

On a first date, questions gather facts. After years together the facts are known, so the useful questions are about the present: what has changed, what they need more of, what they would like to stop doing.

How many questions should we ask on a date?

Three or four with real conversation between them. Working through a long list turns the evening into an interview, which is the opposite of the intent.

Keep going

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