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80+ Funny Questions to Ask on a First Date

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This post is all about funny first date questions and some useful tips to have a great time.

Dating can sometimes feel like an interview. You have to go through the tedious process of trying to summarize who you are in a way that feels honest but also interesting. You can’t just list the most basic facts. Your date also expects you to be entertaining.

When the chemistry is hot and the conversation is flowing, it’s not hard to inform and entertain. But how are you supposed to break the ice in the first place?

Here are over 80 funny first date conversation starters to help you elevate your date, get a laugh, and get to know each other better. 

Funny First Date Questions to Have a Great Time

A Few Ice Breakers 

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

2. What’s your absolute favorite meme?

3. What song would you sing at karaoke if you absolutely had to participate?

4. What’s the best (and worst) Halloween costume you’ve ever worn? 

5. If you had to give a TED Talk on any subject without preparation, what would it be?

6. What’s the most random and/or embarrassing thing you’re afraid of?

7. What was your worst or weirdest first date?

8. What’s the weirdest gift you’ve ever received or given?

9. What movie can you quote all the lines from?

10. Does pineapple belong on pizza?

Questions About Their Childhood

11. Who was your first celebrity crush?

12. What’s the worst fashion trend you’ve ever participated in?

13. Have you ever participated in a flash mob or other social media challenge?

14. How old were you when you stopped believing in Santa Claus and the Tooth Fairy?

15. Have you ever had a crush on a cartoon character, and who was it?

16. Who is the craziest member of your family?

17. What was your favorite show as a kid?

18. What was your favorite show as a teenager?

19. What was your first concert and your best concert?

20. What TV show best describes your family dynamic?

21. What three words would your parent/guardian use to describe you?

22. What posters were on your walls as a teenager?

23. What’s the most stereotypical trait of your Zodiac sign that’s actually true for you?

24. What is the weirdest thing you’re known for in your family?

25. If you had a hot tub time machine, what’s the one fashion trend you’d go back and tell yourself to skip?

Questions About Them at School or at Work

26. What job are you totally unqualified for that you think you would still be good at?

27. Which Breakfast Club character were you most like in high school?

28. What’s the worst and the best reasons you’ve ever called out of work for the day?

29. Would you still work if you won the lottery, or would you quit immediately?

30. What’s the most unnecessary lie you’ve ever included on your resume?

31. What do you actually do for a living vs what people think you actually do?

32. Who would be the best and worst coworkers to be stuck in an elevator with for a day?

33. What theme song should play when you walk into work or school?

34. What would be your job during an apocalypse?

35. What part of your work or school day is absolutely, weirdly sacred to you? 

Questions About Love and Dating

36. Who would you Marry, Kiss, and Kill from the cast of The Office?

37. What celebrity couple is your most favorite? Which one is your least favorite?

38. What emoji best describes you if you could only pick one?

39. What emoji do you irrationally hate and never use?

40. What’s the weirdest thing that’s ever happened to you on a date?

41. What’s the worst pickup line you’ve ever heard (or used)?

42. What pet names do you irrationally hate?

43. What is your most annoying habit? 

44. What is the craziest thing you’ve ever done for love?

45. If you had to live with one ex for the rest of your life, which one would it be? If it’s absolutely none of them, how would you fake your death and where would you go? 

Other Questions

46. What Taylor Swift era are you in if you had to pick one?

47. What is your favorite weird food combination?

48. What is the nerdiest thing about you?

49. What’s one thing about you that is totally basic?

50. If you could only have one social media app, which one are you choosing and why?

51. Which character on Schitt’s Creek speaks to you the most, spiritually?

52. What book do you say you’ve read but have never actually picked up?

53. What movie does everyone else love that you’ve either never seen or completely hate?

54. Which fandom do you think is the most ridiculous?

55. Do you prefer Team Peeta or Team Gale? 

56. What’s the weirdest recurring dream you’ve ever had?

57. Which celebrities would make your Hall Pass list?

58. Which Hogwarts House would you be sorted into?

59. Which super villain do you most vibe with if you had to choose?

60. What childhood cartoon would you most want to see a live action remake of now? 

61. Which celebrity should play you if your life was a movie?

62. What song would you want to play if you were being auctioned off for a date night for charity?

63. What movie quote do you use most often?

64. If you could eliminate one random band or artist from history, who would it be and why?

A Few More Questions

65. Which condiment do you irrationally and completely hate?

66. If your pet gave you a name, what would it be?

67. Which celebrity couple’s relationship are you overly invested in?

68. If there was a reality show about your life, what would it be called?

69. A friend calls and asks you to help them hide a body — which friend is on the phone, and would you help them out?

70. Would you rather have the Sunday scaries or a case of the Mondays?

71. If you could only read one author for the rest of your life, who would you choose?

72. What’s a television series you’ve binged countless times?

73. What is the weirdest thing you bought or learned during the pandemic?

74. Would you rather be a werewolf or a vampire?

75. What would your stripper name be if you had to choose right now?

76. Have you ever been told you look like a celebrity? Which one?

77. If your DJ name was a combination of your first pet’s name and your favorite snack, what would it be? 

78. What fact about your past automatically makes you sound ancient?

79. Would you rather fight dinosaurs or zombies in hand-to-hand combat?

80. Have you ever had an alien or UFO encounter?

81. Have you ever seen a ghost or been in a genuinely haunted house?

Don’t Make It (Too) Weird: Tips for Enjoying a First Date

Even these hilarious and weird inquiries can become tedious if you turn them into a question-by-question interview process. You’re certainly welcome to cover all those funny first date questions, but it’s also perfectly acceptable (and even better) just to keep a few of these questions in mind and then let the conversation flow naturally from there.

Read the Room

Be sure to read the room and don’t make it too weird. You might be genuinely curious to know what serial killer name they would choose from themselves, but that’s one of those questions likely to make a first date nervous — unless you met as a part of a True Crime fandom.

It’s cool to be weird, but don’t make it so weird that your date feels unsafe or uncomfortable.

If your date doesn’t have an answer for one of the questions, learn to let it go. Don’t keep asking or treat them like they’re crazy because they aren’t sure what job they would have in an apocalypse or what superhero name they would choose if they had to pick one.

Your date could be nervous, shy, or simply not into the question. It’s okay to move on if you notice the signs that they just aren’t enjoying your attempts to lighten the mood.

Recommended read: 12 Signs a Guy Enjoyed the First Date with You

Be Creative

If you want to make the first date seem less like pressure and more like fun, choose something other than drinks, dinner, or a movie. Think of a fun outing in your area that allows for conversation to flow in a relaxed environment.

If you abhor bowling shoes, look for a different activity that could appeal to you both. Shared interests are a good place to start.

Look for fun activities in your area. Think outside the box but apply some logic. An escape room can be fun if you already vibe with them, but it could get awkward fast if there’s no in-person chemistry or interest.

An axe throwing gym could offer a relaxed venue — unless your date has already informed you that they are clumsy and accident-prone. An indoor rock-climbing gym might appeal to the more athletically inclined, but it might not be the best pick for someone terrified of heights.

Painting a canvas might sound fun to you but be their idea of a boring night out. Talk it out. Figure out what you both might be interested in doing. 

Recommended read: 60+ Unique Fun Date Ideas for a Guaranteed Great Time (2022)

Leave Expectations at Home

Instead of showing up to your date looking for your next relationship, your soulmate, or an epic romance, leave your expectations at home and simply show up ready to get to know someone new and have a nice time.

Expectations could put unnecessary pressure on a first date. Simply get to know each other and decide if you feel like this is someone you’d like to continue to know better. 

A first date can help you decide if you want a second one, but it doesn’t necessarily decide your fate or the rest of your life. Calm down and just learn to take things as they come. 

Keep It Respectful and Kind

Dating is hard enough without rudeness. Even if your date doesn’t think your questions are hilarious, it’s no reason to be defensive or rude in return. Stay respectful and kind whenever possible. Even if it doesn’t work out, it doesn’t have to be the worst night ever. 

Going into that first date can be awkward. You have all the nerves, and you’re trying to figure out if that’s your lunch trying to make a reappearance or if you’ve just got butterflies in your stomach because you have a crush.

You can use these funny questions to break the ice and get to know the other person better. If you’re willing to give it a try, you just might elevate your dating game to the next level and have a fun night no matter how you feel about each other.

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Photo by Karsten Winegeart on Unsplash

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