97 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 fun and flirty icebreakers for dates.

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Tips on Asking 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

97 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?

couple laughing outside icebreaker questions for dating

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?

couple having cocktail at bar icebreaker questions for dating

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?

Icebreaker Questions for Dating Apps 

76. How many dating profiles do you currently have active?

77. What’s the most number of people you’ve talked to at once on a dating app?

78. What’s the quickest you’ve ever slept with someone you met on a dating app?

79. Do you only date “online?” When’s the last time you went out with someone you met “in person?”

80. What’s your favorite dating app?

81. Have you ever met someone through a dating app, and the relationship blossomed into something serious that lasted over a year?

81. Did you write your profile all by yourself, or did you have friends help?

83. How long did it take you to pick your profile picture?

84. How much airbrushing and filtering did you use on your pic?

85. Have you ever lied about yourself on a dating profile? What did you embellish or leave out?

86. At what age did you make your first online dating profile? Did it take you a while to find matches?

Random and Fun Icebreaker Dating Questions

87. Were you ever attracted to someone that all your friends thought was a terrible person? What about someone who your friends didn’t find the least bit attractive?

88. If you could confront one of your teachers from the past, who would it be and why? 

89. What board game did you hate to play as a kid (or now) just because you’re not good at it?

90. A breaking news alert interrupts and says nuclear weapons have been deployed. What do you do? Who would you call first? Do you think you’d be calm or flip out?

91. If you could only watch Netflix, Hulu, Amazon prime, or Apple TV for the rest of your life, which streaming service would you pick and why?

92. Have you ever gotten into an ongoing row with a neighbor to the point where they became a nemesis? 

93. If a study could prove there was one vice (alcohol, tobacco, cannabis, et cetera) found not to be damaging, which would you hope it was?

94. With whom would you rather be stuck on a deserted island: Jackie Chan, the Rock, or Russell Crowe? 

95. Do you see yourself more as an alpha, beta, gamma, delta, omega, or sigma personality type? How do you think others see you?

96. What is the dumbest or silliest thing you’ve ever said or done on a first date?

97. Would you rather spend an evening at the ballet, opera, or symphony? You have to pick one.

Best Icebreaker Questions for Dating That Are Unique and Memorable 

Still in search of icebreaker questions for a date? Here’s another batch of unique and memorable inquiries to get the conversation flowing.

1. Were you an ugly baby?

Hey, it’s memorable! 

This is the kind of question that could catch someone off-guard (in a good way) and make them howl with laughter. Moreover, your date’s answer could reveal a lot about their personality. 

For example, if you think it’s a funny inquiry, and your date is appalled you could ever ask such a thing, you’re probably not compatible on the humor front, and that can be an insurmountable difference. Similarly, if your date is offended, they may fall on the insecure end of the personality scale. 

What makes it memorable is that people usually fawn over infants, and suggesting otherwise is intriguingly subversive. 

Follow-up questions could revolve around whether or not they’ve seen a lot of pictures of their parents as babies and what they thought of their appearances. 

2. Have you ever done a no-spend or low-spend year?

Financial times are tough, and many people are challenging themselves to no-spend or low-spend years — i.e., 12 months of not buying things you don’t need. 

For example, someone on the no-spend track may only shell out dollars for food, shelter, hygiene, transportation, and utilities. People on low-spend years may also allow for a clothes budget, dinners out, or allotments for hobbies and light travel. 

3. What is the next big purchase you want to make?

The answer to this question will reveal a lot about your date’s passions, priorities, and resource management skills.

Not saving for anything may indicate that they don’t have disposable income, hobbies, or interests — and that’s fine. If they have a nest egg and explain what it’s for, the conversation can go in many different directions. 

For example, “saving up for a vacation” leads to many follow-up questions, including: Why did you choose to go to [insert place]? How long have you been planning the trip? What was the last big vacation you took? What was the first vacation you ever took? 

4. What would your dream job be if money wasn’t an issue?

Let’s face it: Most people don’t earn a living doing what they love. Is it ideal? Absolutely. But life’s realities can be a lot more limiting.

This question provides insight into what your date values and is passionate about, which will reveal a lot about who they are and how they see the world. Note if their interests align with yours and use similarities to keep the conversation going.

5. Do you have a bucket list? What’s at the top of it?

A bucket list is a roster of things someone wants to do, see, try, or eat before kicking the proverbial bucket. Ask your date if they have one. How long have they had one? Do they realistically think they’ll check off each one?

This is another question that opens the window to your date’s hobbies, interests, and sometimes even their worldview. 

Consider whether you find their answers intriguing or disturbing. Are your interests compatible or disparate? 

While you needn’t have the exact interests as a potential romantic partner, people who are complete opposites have less chance of making it work. While opposites attract in some ways, relationships based on shared desires and goals are typically more satisfying and last longer. 

6. Who was the worst boss you ever had, and why?

Some folks argue that you haven’t lived until you’ve had a terrible boss. If you’re in your teens or early twenties, this question may not work. Otherwise, most people have horror stories about impolite, narcissistic, overly demanding, mercurial, greedy bosses. 

Workplace stories can be a lot of fun; plus, it gives the person telling the tale an opportunity to vent — which is almost always appreciated.  

7. What would you say is your worst habit? What about your best?

In some ways, habits define us. So probe a bit. 

Offer up your own faults and strong suits, too. After all, you don’t want to come across as a know-it-all goody-two-shoes. We all have flaws; share appropriate ones.

What do we mean by appropriate? If it’s your first date, there’s no need to tell your date about bathroom habits or other equally personal things. Keep things light and fluffy. If it works out, there will be plenty of time to reveal more. 

8. If your parents, siblings, or best friends didn’t like who you were dating, would you break up with them?

Have you ever broken up with someone because your friends and family didn’t like them? Find out if your date has done the same. 

Not only is it a fun question, but their answer will unveil how close they are to the people in their lives. Will you need to earn approval from a gaggle of folks, or is this person more of a loner? Or perhaps they are close to their loved ones but don’t follow everything they say.

9. What part of your daily routine do you wish you could eliminate?

Many people feel like there aren’t enough hours in the day. Uncover your date’s practical peccadilloes by throwing out this question. 

Before you ask, make sure you also have an answer. It’s okay to prep for dates, so give it some thought. We won’t tell you planned your witticisms.  

10. Have you ever pretended to be interested in something to impress a crush or someone you were dating? How long did you keep up your fake interest?

Being authentic should always be the goal. But we’re humans, and everyone puts on airs and graces occasionally — or pretends to be interested in something they’re not in an effort to impress.

Asking something along these lines will give you an idea of your date’s level of self-assurance. If they can admit to “putting on a front” and laugh about it now, they’re probably emotionally mature and don’t take themselves too seriously.

They may have a tad more growing to do if they insist they’ve never been anything but themselves. 

11. If it could only be one season year-round, which would you choose?

Is your date a winter, spring, summer, or fall person? Find out by popping this question. But don’t let them pick multiple seasons. The idea is to choose a winner.  

While this is a relatively innocuous inquiry, it reveals your date’s preferences when it comes to Mother Nature’s moods. Moreover, if you are a dedicated ski bum, for example, and they loathe coldness, it could be a sign of incompatibility. 

Of course you shouldn’t discount someone if they’re more of a summer person than yourself or vice versa. But it’s something to think about. After all, what if things do get serious? Will you constantly fight about where to spend vacations?

12. Which one of your friends is the most like you? The least?

Try to get a smidge of insight into their friendships with this question. It’s not prying but will also give you an idea about the types of people in their crew.

Furthermore, it provides several avenues for follow-up questions, like how they met their buddies, how long they’ve known them, and how much time they spend together.

Is your date one of those people who can’t go two days without seeing their pals, or have they adopted a once- or twice-a-month hangout schedule? 

Fair warning: Age will play a massive factor. Younger people tend to see their friends more than older ones.

13. What was your first computer? How old were you?

If you’re in your twenties or thirties, move on to the next question because you’ve likely had a computer since you can remember. But if you’re about 42 or older, you likely have fond memories of getting your first “magic machine.” 

Expand the conversation by asking what they did on their PCs or how quickly they became a “Mac person.” Inquire about video games they played and if they got into coding early on.  

14. What group, if any, did you hang out with in your teenage years?

Most high schools are segregated by group: the jocks and cheerleaders, band folks, academic clubs, theater people, et cetera. Find out what crew they stuck to. 

But remember that many people had terrible high school experiences that they don’t necessarily want to talk about on a first date. Be mindful and pay attention to their reaction. Let it rest if they don’t seem like they want to delve into this line of questioning. 

15. Have you ever had a moment when you realized you weren’t nearly as intelligent, sophisticated, or right-thinking as you thought you were?

This is another question that has the power to reveal how your date sees themselves and whether they’re sufficiently humble. Not being able to think of a single time they came up short may signal a wildly inflated ego. 

We’re not suggesting you grill your date about their insecurities or shortcomings. That’s awkward and uncomfortable. But mature adults should have the self-awareness to pinpoint a time or ten when they made the wrong call. This type of vulnerability reveals a lot about a person’s character.

16. If you could only stream movies, go to museums, or exercise for one year as your sole source of entertainment, which would you choose?

Is your date more of an academic, sports enthusiast, or cinephile? This question will reveal all. Again, weigh their answer as a compatibility marker. 

For instance, if they would rather spend a year joining teams, running, and hiking, and that sounds like hell on Earth to you, maybe you’re not the right match.

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.

Sometimes, it's awkward between you and your date. Learn these icebreaker questions for dating and have a fun conversation with them.