37 Questions to Ask on a First Date


Living in the DC area I have been asked “what do you do?” numerous times, and every time I was annoyed. A city with some of the country’s brightest people could come up with something more creative to ask. I will explain later why this is a terrible question but for now, here are 37 other questions you can ask to start a conversation.

1. What are you passionate about?
2. What is your biggest fear?
3. What was your most embarrassing moment?
4. Who do you look up to? Fictional or real.
5. If you could have one superpower what would it be?
6. Who do think are the top 5 best rappers of all time? (If they aren’t into hip hop skip this one)
7. What is the best dish you have ever ate?
8. Where in the world would you live if not here?
9. What was the best vacation you’ve ever taken?
10. What was the last thing you watched on Netflix?
11. What is your earliest memory?
12. What would you do if the zombie apocalypse happened tomorrow?
13. What does your dream home look like?
14. What is your favorite song?
15. If you could witness any historical event what would it be?
16. Chicago style pizza or New York style pizza?
17. Did you play sports as a child?
18. Batman or Superman?
19. Fresh Prince or Martin?
20. What is your favorite museum in DC? (Replace DC with your respective city)
21. Mac or PC?
22. What is your favorite type of cookie?
23. What is your favorite childhood book?
24. What is the best concert you attended?
25. What toppings does your ultimate pizza have? (Note: if they don’t like pizza block their number)
26. What is your guilty pleasure?
27. Do you have a hidden talent?
28. Did you grow up here?
29. Which artist would you bring back from the dead to attend one of their concerts?
30. What movie can you watch over and over and never get tired of seeing?
31. What did you study in school?
32. Are you still friends with your childhood best friend?
33. What do you like to do in your spare time?
34. Do you like sports? Who are your teams?
35. What is something you recently accomplished that you are proud of?
36. Trader Joe’s or Whole Foods?
37. What is the last book you read?

As you can see these questions are not personal, don’t touch on controversial topics (sex, politics, religion), and allow you to get to know someone on a more personal level. Personally, I don’t see what knowing what someone’s job is has to do with making a connection and building a relationship. We are not our jobs and they should not play a huge role in our social lives. Also, why are we talking about work in the first place? If work comes up, it should happen organically.

That said, try out some of these questions. You will be amazed how much better conversations can be when you take “what do you do?” out of it.

What are some questions you ask during dates? Share them below!


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