The best dates aren’t about the restaurant or the wine. They’re about the conversation. And the best conversations start with the right question — one that makes the other person pause, think, and say something they didn’t plan to say.
Whether you’re on a first date trying to skip the small talk, or you’ve been together for years and the dinner conversation has become a logistics meeting — these questions will change the evening.
First date energy
These are designed to be interesting without being intense. Light enough to feel fun, specific enough to reveal something real.
1. What’s something people always get wrong about you on first impression?
2. What’s the most spontaneous decision you’ve ever made?
3. What’s a compliment someone gave you that stuck?
4. If you could live anywhere for one year, no strings attached, where would it be?
5. What’s the best meal you’ve had this year and what made it special?
6. What were you obsessed with as a kid?
7. What’s a talent you have that nobody would guess?
8. If your life had a theme song, what would it be right now?
9. What’s the last thing that genuinely made you laugh?
10. What’s your favourite way to spend a Sunday?
Getting warmer
For when the conversation is flowing and you want to take it a level deeper. Second or third date territory, or any couple that’s ready to go past the surface.
11. What’s something you’ve changed your mind about in the last year?
12. What does your ideal day look like — not vacation, just a regular Tuesday?
13. What’s a relationship lesson you had to learn the hard way?
14. What quality do you value most in a partner?
15. What’s something you wish people asked you about more?
16. What were you like as a teenager?
17. When do you feel most like yourself?
18. What’s something you’re quietly proud of?
19. What does “home” feel like to you?
20. What’s the kindest thing anyone has ever done for you?
Long-term couples: break the routine
These are for partners who know each other well — or think they do. The goal is to find the corners of the other person that routine has covered up.
21. What’s something about our relationship that you think we should talk about more?
22. What’s a dream you’ve quietly shelved since we got together?
23. When do I make you feel most loved?
24. What’s something I do that you’ve never told me you appreciate?
25. If we met for the first time today, what would you notice about me?
26. What’s a memory of us that you replay when you’re having a bad day?
27. What’s something you miss about the early days?
28. How have I changed since we met?
29. What’s something you need from me that you haven’t asked for?
30. If we could do one thing differently from the start, what would it be?
Bold and spicy
For couples who are past the point of filter. Honest, direct, and guaranteed to shift the energy.
31. What’s a fantasy you’ve never told me about?
32. When are you most attracted to me?
33. What’s the biggest misconception about our relationship from the outside?
34. What’s something you’d do differently if you were single for a month?
35. What part of our relationship would you rate 10/10?
36. What’s something you thought would bother you about a relationship but doesn’t?
37. What’s a question you’re afraid to ask me?
38. When was the last time I surprised you?
39. What’s a secret you’ve been meaning to tell me?
40. If you could change one thing about how we communicate, what would it be?
How to use these
Don’t use them as a checklist. Pick one or two. Let the conversation go where it goes. One good question can carry an entire evening.
Answer first. Don’t just fire a question across the table. Say “I was thinking about this — here’s my answer” before asking theirs. It sets the tone and makes the other person feel safe being honest.
Put the phone away. These questions deserve eye contact. The screen can wait.
Don’t judge the answer. The whole point is to learn something new. If they say something that surprises you, lean in with curiosity, not correction.
The best date nights don’t cost money. They cost honesty. And the return on that investment is a relationship that keeps getting deeper instead of settling into comfortable autopilot.
Want these on-the-go? Ohh has decks built for exactly these moments — Love Languages, Deep Dive, Bedroom Confessions, and more. Pull out the app at dinner, pick a card, and let it do the work. Or send your partner a Spark before date night so you both arrive with something real to talk about.
Tonight, skip the “what should we eat?” conversation. Ask something that matters instead. Your next great date night is one question away.