36 Questions to Fall in Love: An Original Date-Night Guide

Start with the meal you’d eat every week; end with something you’ve been meaning to ask each other. These 36 original date-night questions move from everyday tastes to trust, affection, and the two of you. They’re an alternative to the familiar “36 questions to fall in love,” not a reproduction of the original questionnaire. No list can promise romantic feelings.

Take turns, with both of you answering each question. Either person can pass without explaining. Follow an interesting answer instead of racing to finish; stop after any round. On a new date, try the first round before deciding together whether to continue.

Start with the everyday stuff

1. Which meal could you happily eat every week?
2. What’s your most useless talent?
3. Think of the last time you laughed so hard you couldn’t finish a sentence. What set you off?
4. If we had a free afternoon and a $20 budget, how would you want to spend it?
5. What completely unimportant opinion would you defend for twenty minutes?
6. Is there a place you’ve visited only once but still think about? What do you remember most clearly?
7. Pick a song that takes you back to a particular year. What scene from your life comes to mind when you hear it?
8. On a trip, which part do you like planning, and which part would you rather leave open?
9. What’s one thing at home you’d miss if it disappeared tomorrow, even though a guest might never notice it?
10. Who taught you a skill you still use, and what do you hear them saying when you do it?
11. Describe a day off that would leave you glad you stayed home.
12. As a kid, what grown-up privilege were you most excited to get—and does it live up to the hype?

The people and choices that shaped you

13. Which compliment has stayed with you?
14. What did your family do that you assumed every family did, until you found out otherwise?
15. When you’re stressed, would you rather have company, practical help, or space—and how could I tell which you want?
16. Is there a choice you’re proud of even though it didn’t work out the way you hoped?
17. Who gets a side of you that most people don’t see? What are you like around them?
18. What’s something you’re a beginner at right now, or would like to be?
19. Think of a routine you’ve kept for years, like a Sunday phone call or a walk after dinner. What makes you keep showing up for it?
20. What have you changed your mind about in the last few years?
21. If you’d taken a different path at one turning point in your life, where do you imagine you’d be now?
22. Do you keep an old ticket, recipe card, or other object that wouldn’t mean much to anyone else? What’s its story?
23. How do you recognize someone you can trust?
24. Which part of your life feels most like a choice you made for yourself, rather than something you were expected to do?

A little more personal

25. What takes people a while to notice about you?
26. When you picture feeling at home with someone, what are the two of you doing on an ordinary Tuesday evening?
27. Finish this thought: “I tend to show I care by…” Is that also how you like someone to show care for you?
28. Which kind of help is hardest to ask for?
29. During a disagreement, how could either of us ask for a break without leaving the other person wondering where things stand?
30. Is there a place you’d like to show me—a hometown diner, a favorite trail, or somewhere else that tells me something about you?
31. What’s your first memory of us?
32. Which answer of mine tonight would you like to hear more about?
33. What’s something about me you’d brag about to a friend?
34. Where do you think we’re alike in a way that isn’t obvious at first?
35. Suppose we both had a busy week and hardly talked. What’s a way we could reconnect that you’d actually look forward to?
36. What would you like to ask me that you haven’t found a chance to ask?