75 Fun Icebreaker Questions For Dating

Maybe it’s your first date or third.

Whichever the case, you’re in the market for conversation starters to avoid awkward silences.

We understand!

Dead space is disconcerting during the early dating days.

So to help you get over the hump, we’ve curated a list of 75 fun and flirty icebreakers for dates.

What Are Some Unique Icebreaker Questions?

Once the normal questions — where do you work, where do you live, how old are you — are out of the way, then what?

If you’re lucky, there’s instantaneous chemistry, and the two of you gallop off into the conversational sunset like a pair of bonded thoroughbreds.

Sometimes, though, jump-starting a tête-à-tête takes a bit of effort. If you want to demonstrate that you’re not a normcore android, start by asking unique icebreaker questions.

But be careful because there’s a razor-thin difference between probing and problematic. Unique icebreaker questions should:

• Be endearingly quirky, but still within the realm of acceptable
• Demonstrate that you’re genuinely interested in getting to know the other person
• Create avenues for follow-up questions
• Be amiable and not purposefully contentious

75 of the Best Icebreaker Questions for Dating

We’ve discussed what not to say and the formula for fun dating conversations. Now it’s time to create a toolkit of dating icebreaker questions.

We’ve divided our list into four sections: general, first date, funny, and online.

All of them may not be appropriate for your situation, so take what works!

Good Icebreaker Questions for Dating

1. Do you miss your hometown, or are you glad to be gone?

2. Have you ever had a celebrity encounter?

3. Do you like to travel? If so, what’s the most [exotic/fun/fascinating/remote] place you’ve been?

4. Where is the one place you’ve never been that you’d like to go?

5. Do you have any hobbies?

6. Are you an animal person? Do you have any pets? What’s your stance on zoos?

7. Do you have a lot of pet peeves? Which one takes the prize?

8. What’s the last movie you saw in a theater? At home?

9. Do you have a preferred streaming platform? Are you more of an Amazon Prime, Netflix, or Hulu person?

10. Is there anything about yourself that you’re currently trying to change?

11. Were you an awkward or cool kid in elementary school?

12. Do you play any sports?

13. Are you a foodie, or do hot pockets and ramen noodles suit you just fine?

14. Can you cook? Do you enjoy it?

15. Do you drink alcohol? If so, are you more of a beer, wine, or hard liquor person? Follow-up question: When did you start drinking?

16. Are you pro- or anti-holiday? What are your thoughts on Halloween?

17. Who is your biggest celebrity crush?

18. Do you have a hero? Who is it, and why do you admire them?

19. What’s your go-to karaoke song?

20. Are there websites you check out daily? If so, which ones?

Icebreaker Questions for a First Date

21. Name one food you would absolutely never try even if someone offered you a hundred bucks to taste it.

22. As a child, what did you want to be when you grew up?

23. Are you a fan of surprises?

24. Do personal or professional achievements matter most to you at this point in your life? And no, you can’t say both!

25. Do you have an alter ego? When does it show up?

26. Would you continue working if you won $10 million in the lottery?

27. What is the first vacation you remember?

28. What’s the pillow situation like at your house? Are you a fan?

29. What kind of music do you like? I know it’s impossible to pick one favorite artist or group, so who are your top five?

30. What’s your favorite old-school television show?

31. In terms of comics, are you a Marvel or DC fan?

32. If, for some reason, you had to move out of [insert country], where would you choose to go?

33. What period of history would you most like to live in?

34. If you had to choose between living in the city or country, which would win out?

35. What’s the best piece of advice someone has ever given you?

36. Are you reading any good books?

37. If you could only keep three apps on your smartphone, what would they be?

38. How long have you known your best friend? Why do you get along so well?

39. If you could hire one person to help you live life, what would you have them do?

40. Do you have a work nemesis, or is your office fairly anodyne?

Funny Icebreaker Questions for Dating

41. So, am I your only date this evening, or did you double book?

42. Quick! Someone is offering you a million bucks to do a spontaneous TED Talk. What’s your topic?

43. Are you a self-help person or perfect just the way you are?

44. If you could hop in Doc Brown’s Delorean and travel back in time, what advice would you give a 13-year-old you?

45. ”Airplane” reference: “Do you like movies about gladiators? Have you ever been to a Turkish prison?”

46. What’s cleaner: your bathroom or car?

47. How do you feel about Joe Exotic, aka Tiger King?

48. What makes you curl up into the fetal position and tremble like a baby?

49. If you were a type of mustard, what type would you be? Regular? Dijon?

50. Are you an armchair athlete? If so, which team(s) do you coach?

51. With which emoji do you have an unhealthy relationship?

52. What motivates you to work hard — if anything? I mean, if you ask me, being lazy is an acceptable personality trait.

53. What reality show celebrity are you most like?

54. If you had to sacrifice one of your family members, who would it be and why? Note: This should be reserved for sardonic wits who appreciate humor’s darker side.

55. Zombies have arrived. What three people are you recruiting for your defense team?

56. Tell me about your style [10 / 20 / 30] years ago.

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Online Dating Icebreaker Questions

57. Are you a seasoned online dater, or is this your first time giving it a shot?

58. What are your favorite online dating apps?

59. Why did you decide to give online dating a shot? Note: This is mainly for mature daters who lived when online dating wasn’t the norm.

60. Do you have any wild online dating stories?

61. What was the biggest shock you’ve had while online dating? Has anyone completely misrepresented themselves to you?

62. What’s the most spontaneous thing you’ve ever done with someone you have never met in person?

63. Are you an early bird or a night owl?

64. How did you feel about the ending of “Lost”?

65. What is your sense of humor? Are you more slapstick or sarcastic?

66. Of which fictional family would you want to be a member?

67. What scientific phenomenon blows your mind?

68. Do you have children? What do they want to be when they grow up?

69. Who is your favorite YouTuber?

70. Do you check your horoscope daily? Do you know your Chinese zodiac sign?

71. Do you have any tattoos?

72. Have you ever gone a long time without sleep? If so, why? How did it make you feel?

73. If you could redesign Mount Rushmore, who would be on it?

74. Lenin or McCartney? Beyonce or Rhianna? Tim McGraw or Luke Bryan? Oasis or Blur? Britney v. Jamie Lynn?

75. What was the last thing you binge-watched?

If you keep things light and enjoy the exercise of meeting new people, dating can be a lot of fun!

Even if it’s not a romantic fit, having a repository of conversation starters in your proverbial back pocket will keep things pleasant, friendly, and upbeat.