Our Matchmakers Top 49 Ultimate Questions To Ask Someone in 2025 To Get To Know Them Quickly On A Date

1. If you're sitting next to someone on an airplane and they fall asleep but you have to pee do you wake them up or try to shimmy around them?
2. What has genuinely surprised you?
3. What's your favorite film?
4. Tell me about an adventure you went on recently.
5. One word to describe yourself
6. What have you made recently?
7. What music gives you goosebumps?
8. What are you obsessed about?
9. What do you irrationally hate?
10. Before making a phone call, do you ever rehearse what you're going to say? Why?
11. What would constitute a perfect day for you?
12. When did you last sing to yourself?
13. If you could change anything about the way you were raised, what would it be?
14. If you could wake up tomorrow having gained one quality or ability, what would it be?
15. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
16. Is there something that you've dreamt of doing for a long time? Why haven't you done it?
17. What do you value most in a friendship?
18. What is your most treasured memory?
19. When did you last cry in front of another person?
20. Which historical time period would you most like to visit?
21. Who do you think is the most inspirational person alive today?
22. What would you love to find at a yard sale?
23. What's on your bucket list that nobody would ever guess?
24. Would you rather meet your great-grandparents or your great great grandchild?
25. What do you think is the ideal age?
26. In which activity would you like a lesson from an expert?
27. Which of your personality traits would you like to change?
28. If you could have front-row seats at any concert, who would you like to see?
29. What fashion trend you followed was cool then, but now looks ridiculous!
30. Would you rather vacation in a big city or the countryside?
31. What's your dream job?
32. Favorite dessert?
33. What do you wish you were better at saying “no” to?
34. What would you most like to do for someone else if you had the money and time?
35. What would you do if you had no fear?
36. What was your favorite game to play as a child?
37. Where would you choose to live if you had to leave the country?
38. What makes a house a home?
39. What was your favorite childhood meal?
40. Have you ever had an experience that led you to believe in angels or ghosts?
41. If you lived to be 100, would you rather have a sharp mind or a fit body?
42. If you could be brilliant at one subject, which would you choose?
43. Do you have any superstitions?
44. What's the hardest thing you’ve ever done?
45. What obligation do you believe you have to your county?
46. How do you define success?
47. What would you miss most about your home if you moved?
48. What's one goal you hope to accomplish this year?
49. What's your proudest accomplishment?

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