31 Random Questions To Ask On A Date That Could Actually Lead To A Good Conversation

If you're anything like me and you loathe awkward silences, then the pressure to keep the conversation flowing on a first date can be a killer. I mean, how many times have you been on a date and the conversation just suddenly dries up? Total nightmare. To make things even worse, it’s not because there isn’t a vibe there. If anything, the more I've been into someone, the more likely my brain is to totally flatline. So, to avoid these excruciating moments, I've learned to have a few go-to questions to ask on a date that are guaranteed to turn an awkward silence into a good conversation.

Anyone who knows me would probably think my first date conversational paranoia is crazy, because normally I always have plenty to say. But there’s just something about small talk. It's my kryptonite. My brain, normally overflowing with too many words, is suddenly empty. What I've come to realize is that this happened because I’m just not interested in light chit chat. I want to talk about real stuff. I want to get deep right away. But that's not always great on the first date. It's all about finding that happy medium between dull small talk and going full-on Dr. Phil on your date. So here's some ideas of what is good to ask on a first date and when it's OK to dig a little deeper.

Questions To Break The Ice

1. What’s something people wouldn’t guess just by looking at you?

2. When you were growing up, what was your favorite TV show?

3. Where is somewhere you’ve always wanted to travel to all by yourself?

4. Where have you traveled to? And where do you want to go next?

5. What’s the most spontaneous thing you’ve ever done?

6. If you could have any talent in the world, what would it be?

7. What’s something you’re terrible at?

8. What's something "weird" you believe in that most people don't?

9. Which fictional character do you relate the most to?

10. What are some things that really make you laugh?

Questions To Dig A Little Deeper

11. What’s something that comes easier to you than it does for most?

12. What’s your favorite place in the world?

13. What's the most crazy thing you've ever done?

14. Did you have any weird or quirky habits as a kid?

15. Do you consider yourself an adventurous person? Provide receipts please.

16. What’s something you used to do as a kid that you really miss now?

17. If you could become anyone for a day, who would you be?

18. What is something you feel really passionate about?

19. What's the stupidest thing you’ve ever done for the sake of love?

20. What stereotype about men/women do you hate the most?

Questions To Get The Real Tea

21. Who in your life has been the most influential for you?

22. What are three things you want to have accomplished before you die?

23. What’s the best advice anyone has ever given you?

24. What in your life are you must grateful for?

25. What accomplishment are you most proud of?

26 Do you think you have a purpose in life?

27. What’s one fear you know is holding you back?

28. What makes you feel the most fulfilled?

29. What is the number one thing in your life that you are not doing that you wish you were?

30. What has been your bravest moment in life?

31. Have you ever been to arrested or gone to prison?

Whew, that last one is a biggie. While I stand by all of these questions as a great way to get a conversation going, I can personally attest to having been surprised by the answer I once received to that final one. I asked it jokingly and got a real response. Glad I asked it, and I followed it quickly with one more... to the waiter: Can I get the check please?

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