Online Reporter
If you want to start off light and casual
1. What were you doing before this date?
2. What’s been the highlight of your week so far?
3. What’s your go-to order at a place like this?
4. How do you spend a typical week?
5. What do you usually do in your free time?
6. What are some hobbies you’ve been wanting to learn or get better at?
7. What’s your all-time favourite (book, movie, show, game, etc.)?
8. Do you like to travel? What has been your favourite place so far —or what’s on your wish list?
9. What type of music do you usually listen to?
10. How long have you lived in _____? Would you ever consider leaving?
11. If you could trade lives with anyone for a day, who would it be and why?
12. Who do you usually call when you’re having a bad day?
13. What’s the most random thing on your bucket list?
14. How do you feel about social media? Do you have a favourite app?
If you’re looking to learn more about them — without overstepping
15. Are you more of a texter or a caller?
16. How would your closest friends describe you?
17. Among your friends, what are you best known for?
18. Who is the person you look up to the most?
19. What’s something you wish more people knew about you?
20. Did you set any goals this year? What were they?
21. What’s one thing you hope to accomplish in the next five years?
22. What’s something you do every single day without fail?
23. How do you feel about your current job? If money weren’t a factor, would you pursue anything else?
24. What’s one topic you could make a whole TedTalk about?
25. What’s your biggest Pet Peeve?
26. Do you tend to be more of a planner or more spontaneous?
27. What’s one thing you really value in your friendships?
28. What are your hidden talents?
29. What are some accomplishments you’re really proud of?
30. If you could have any superpower, what would it be?
31. What wrong assumptions do people make about you?
32. Is there anything in your life that you feel like you’re missing—like a specific achievement or experience?
33. Who’s the person you talk to most in your life?
34. What’s one thing you’re always willing to splurge on?
If you’re ready to suss out your compatibility
35. What made you want to go on this date with me?
36. What was your first impression of me?
37. I really care about _____. What about you?
38. What’s one date idea you’ve always wanted to do?
39. What are some of your favourite romantic gestures?
40. What are you looking for right now? Something casual? Long-term?
41. What are some of your dealbreakers or pet peeves while dating?
42. How do you handle conflict? Are you usually more upfront or go-with-the-flow?
43. What’s your love language?
44. How long was your most Serious Relationship?
45. What are some non-negotiable things you’d like in an ideal partner?
46. What are the most attractive qualities to you in a partner?
47. How do you prefer to spend quality time together in a relationship?
48. In your opinion, what are the most important factors in a successful relationship?
49. What’s the best piece of relationship advice you’ve ever gotten?
50. What’s the biggest lesson you learned from your last relationship? —Glamour
derick.khumalo