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60 Funny Questions To Ask On A Date (LAUGHTER GUARANTEED!)

Humor is a great and daunting way of breaking the ice on a date. If you’re not naturally funny but want to tickle your date’s funny bone, here are funny questions to ask on a date. 

These funny questions to ask on a date are thoughtfully compiled to help kickstart some amusing conversations. The question is when is it appropriate to ask these funny questions? 

I’ve included several questions that are suitable to ask on a first date when you’re just getting to know each other. However, I also have a list of funny questions to ask on a date when you’ve already built rapport. You’ve already gotten to know your date and want to uncover a different side to them. 

Alternatively, there are questions on this list that you may consider if you’re feeling bold and your date is comfortable around you. So without further ado, here are 60 funny questions to ask on a date. 

Summary

  • Funny questions to ask on a first date 
  • Funny questions to ask on a date – Dating edition 
  • Funny questions to ask on a date – Growing up edition 
  • Funny questions to ask on a date – Perception and Getting to Know Them edition 
  • Funny questions to ask on a date – Experience edition 
  • Funny questions to ask on a date – Opinions edition 
  • Funny questions to ask on a date – Hypothetical situations edition 
  • Frequently asked questions 
    • How can I be extremely flirty? 
    • What is the 3-date rule? 
    • How to innocently make him blush? 
  • Conclusion 

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DISCLOSURE

Some of the links on here are affiliate links and I may earn if you click on them, AT NO EXTRA cost to you. Hope you find the information here useful! Thanks.

Funny questions to ask on a first date 

These funny questions to ask on a date are suitable when you’re just getting to know each other. These ice-breaker questions don’t invite your date to reveal too much but just enough to get an idea of them. 

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1. What’s the worst gift you’ve ever received but had to pretend you loved it? 

2. What’s the worst gift you’ve given? 

3. What’s the most outrageous thing you’ve ever bought? 

4. What’s the most embarrassing song on your playlist? 

5. What’s a movie you frequently watch? 

6. Who would you cast to play you in a movie about your life? 

7. Your go-to karaoke song? 

8. Name an overrated singer, TV show, and movie. 

9. Name an underrated singer, TV show, and movie. 

Funny questions to ask on a date – Dating edition 

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Credit: Pexels 

Dating is hard and sometimes laborious. However, it’s good to inject humor when reflecting on the experience. Hopefully, these fun questions to ask on a date will do just that!

10. Describe your worst date. 

11. How would you leave a bad date without being rude? 

12. What is the worst thing someone can put on their dating app bio? 

13. What’s the cheesiest pick-up line you’ve heard or used? 

14. What’s the craziest thing you’ve done for a crush? 

15. Have you ever lied or exaggerated the truth to impress a date or crush? 

Funny questions to ask on a date – Growing up edition 

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Credit: HuyNgan 

16. If you bring someone new to meet your extended family, who would you warn them about? 

17. What’s a common fact you only realized later in life? 

18. What’s a lie you were told as a kid and believed for too long? 

19. Who amongst your friends and/or family makes you laugh the hardest? 

20. What’s a fashion trend you followed that looking back, made you look ridiculous? 

Funny questions to ask on a date – Perception and Getting to Know Them edition

21. What’s an assumption people have of you? 

22. Do you have any quirks? 

23. What’s a weird thing you do when you’re alone? 

24. Do you pee in the shower? 

25. Do you think it’s okay to fart in your bathwater? 

26. Do you have an embarrassing secret talent? 

27. Which meme best represents your life? 

28. Name a noise that irritates you. 

29. What do you think I do for a living? 

30. What was your first impression of me? 

31. Show me something you read or seen online that made you laugh 

Funny questions to ask on a date – Experience edition 

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Credit: sasint 

32. What have you done that you weren’t proud of? 

33. What’s something embarrassing you’ve done that you’re ashamed to admit? 

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

35. Have you done anything crazy on a night out? 

36. Have you ever stolen anything? 

37. Where was the most embarrassing place you’ve ever farted? 

38. What’s an awkward memory that still haunts you? 

39. Have you ever had a sex dream with someone you know? 

40. When was the last time you laughed hysterically? 

41. What’s one thing you’ll never do again? 

42. What’s a lie you’ve told that you’re embarrassed to admit? 

Funny questions to ask on a date – Opinions edition 

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43. What’s something you’ve thought about but never said out loud? 

44. What do you think of astrology? 

45. What do you think should be banned? 

46. How late is too late to cancel on someone? 

47. What’s your most unpopular opinion?

Funny questions to ask on a date – Hypothetical Situations edition 

48. What would you do if you won the lottery? 

49. What do you think you’d be arrested for? 

50. What’s the first thing you’d do if you became the opposite gender for a day? 

51. Your house is on fire, what’s one item you’d take with you? 

52. How would you fare in a zombie apocalypse? 

53. Name one item you’d use as your weapon during a zombie apocalypse. 

54. If you were the last person on earth, what is the first thing you’d do? 

55. What sport would be the funniest to add a mandatory amount of alcohol to? 

56. If you could be a fly on the wall, where would it be? 

57. Who would you like to switch lives with? 

58. Would you rather have feet for hands or hands for feet? 

59. Would you rather never wear shoes or wear shoes all the time for the rest of your life? 

60. Would you rather never wear shoes or wear shoes all the time for the rest of your life? 

Frequently Asked Questions 

How can I be extremely flirty?

Keep your body language open and approachable. When flirting, research reveals that how something is communicated is as important as what is communicated. A 2021 study suggests that eye contact, a slight smile, and a tilted head can indicate flirtation. 

What is the 3-date rule?

According to the three-date rule, it is best to wait three dates before becoming physical with a potential partner. This rule helps daters navigate the dating landscape, specifically when to be intimate. 

How to innocently make him blush?

Give him an unusual compliment. If you know him well, compliment him on a bold, positive personality trait. Share how kind, confident, and funny he is. Compliments are great in making him feel self-aware and can positively lead to blushing. 

Conclusion 

I hope this list of funny questions will generate excitement for your next date. These funny questions to ask on a date might reveal some outrageous answers so make sure you’re also ready to answer these questions as well. 

Most importantly, don’t forget to listen tentatively, respond authentically, and have fun! All the best!