It can be hard to make conversation on first dates. You're trying to make a good impression and get to know the other person at the same time, and you have to think of interesting things to talk about to boot. In my experience, the best way to get a conversation going is to ask open-ended questions, so here are some ideas to get you started.
1. If you could write a letter to your thirteen year old self, what would say?
2. If you had a time machine and had to choose between going forward or backward in time, which would you pick?
3. What quality about your idols do you admire the most?
4. How far away would you be willing to move for a big promotion at work?
5. What's something that really scares you but you've always wanted to do anyway?
6. What's the craziest fashion trend you ever tried?
7. Do you follow celebrity news and if so, why? Do you consider it a guilty pleasure?
8. What are the best and worst movies you've ever seen?
9. If there was one skill you wish you could acquire instantly, what would it be?
10. If you could live anywhere in the world, money is no object, where would you go?
11. If you could be President for a month, and everything you did would remain in effect afterward, what would you do?
12. What would the title of your autobiography be?
13. What's your worst habit?
14. What accomplishment are you proudest of in your life?
15. If you could say anything at all to your boss, what would you say to him/her?
16. What's your most embarrassing moment, and do you think you'd still be as embarrassed by it if it happened now?
17. What decision in your life do you regret the most?
18. Who was your first fictional crush?
19. What was your favorite book growing up?
20. What character did you connect the most with growing up?
21. Did any of your teachers have a significant impact on you growing up? If so, how, and what was the impact?
22. What historical figure do you admire most?
23. Do you consider yourself to be impulsive or do you like to think things through?
24. Do you like to learn things or acquire new skills just for the sake of it or do you think it needs to have an immediate application?
25. What's your go-to karaoke song?
26. What do you think is your best quality?
27. What was your biggest insecurity when you were a teenager? Is it still the same now?
28. Do you like to travel? If so, where do you want to go next?
29. If you could have been born in another country, which one would you pick?
30. What's something in pop culture that everyone seems to like that you hate?
