#31 Genuinely Interesting Questions For You To Ask Your Next Date

I have a complaint and I am so ready for the internet hate I’m going to get for it. BRING IT ON. As an extrovert I am really good at starting conversations and keeping them going. That being said, I’m really tired of going on dates and not feeling like there’s no give and take. I’m tired of asking all the fun questions! And I’m so sick of the standard “date” questions. It’s really, REALLY attractive when people ask well thought out questions that at least give the illusion that they want to know me better. And I mean REALLY know me. Not just know where I went to college and what my worst OkCupid story is. Good questions are sexy. Hint hint, nudge nudge, fellas.

So here ya go. 30 questions you can bust out on your next date that will make the person sucking their last bit of their vodka soda stop and say, “Wow, what a great question.” My gift to you.

1. Who inspires you? Who do you aspire to be like?

2. What was the last book you read without skipping through anything?

3. What is the weirdest scar you have and how did you get it?

4. What is the most random thing you’ve ever watched all the way through on Netflix?

5. If you could trade lives with one person for an entire day who would it be and why?

6. Do you believe in ghosts?

7. Shark diving, bungee jumping, or sky diving?

8. Which would be harder for you to give up: coffee or alcohol?

9. How did you meet your best friend?

10. Do you have a sweet tooth or a savory tooth?

11. What is something you’ve always wanted to try but have been too scared to?

12. What accomplishments are you most proud of?

13. If you were going to go to the movies alone, what would be the perfect film for you to watch by yourself?

14. What is your favorite Wikipedia article? (Shuddup. Everyone has one.)

15. What is your favorite physical attribute about yourself?

16. Tell me about the best vacation you’ve ever taken.

17. Where is your favorite place to go on a weekday afternoon when you have no plans or obligations?

18. What is one of the weirdest things you used to do as a teenager?

19. Gin, vodka, or tequila?

20. What drives you to do what you do? What motivates you?

21. In your opinion, what is the best Disney movie to come out since Disney s Golden Age?

22. What kind of phone was your first cell phone?

23. What did you love most about the place you grew up? What about it did you love the least?

24. What trajectory are you hoping to push yourself onto? Where do you want to head?

25. What is your most bizarre talent?

26. Is there a documentary or book that really changed the way you thought about something?

27. What are three albums (soundtracks or compilations don’t count) that really define you or have shaped you as a person?

28. Who was someone you really looked up to when you were little someone you considered to be a mentor?

29. What’s your favorite cheesy pick-up line? Have you ever used it for real?

30. Who is a character from a TV show or a book that you ve always resonated with?

31. Can I get you another drink?