The Match Lab

110 Funny Questions to Ask on a First Date


110 Funny First Date Questions (and why they work so well):

1. Would you rather have an angry cat or clingy dog?

In addition to being a funny first date conversation starter, hearing your date’s answer to this question can help you understand how they think about emotions and relationships in their life.

2. If you could pick one day in your life to relive over and over, what day would it be?

This question gives you a great way to get to know someone and relive a fond memory from their life with them.

3. How would your friends react if you quit your job and decided to travel the world?

See how adventurous they are and what their friends think of them vs. how they think of themselves.

4. What’s more likely to exist: ghosts or aliens?

This allows people to share funny stories about beliefs in things no one can prove.

5. If your pet was having a game night with their friends, what would your pet say about you?

Hear what they’re like when they’re being themselves with their pet. Plus, almost everyone with a pet loves talking about their pet.

6. What is your Hogwarts House?

Allows you to figure out their personality. And if they don’t know their house, then take out your phone and have them take the questionnaire online right then and there!

Read: 58 Harry Potter Pick Up Lines

7. Who would play you in a movie of your life?

It shows what they think of themselves. One of the classic best first date conversation starters.

8. If you could only eat one food for the rest of your life, what would it be?

It gives you an idea of their tastes.

9. What color would you describe yourself as and why?

See how they view themselves and what they feel toward certain colors. Everyone has their own perceptions of colors and the emotions tied to them, and it’s fun to get this glimpse into your date’s inner world.

10. Have you ever been pulled over for speeding?

To find out how risky or cautious they are, and maybe get a story out of them.

11. What is your go to karaoke song?

Gives you a sense of what type of music they like, and if they are more introverted or extroverted. This question can also set you up for a future karaoke date.

Read: 7 Best Photos for Your Dating Profile

12. How long could you survive without your phone?

Gives you a sense of how attached they are to their phone.

13. If you could have any superpower, what would it be and why?

Could spark a good discussion, and even a friendly debate, about which powers are better than others.

14. Do you think it’s ok to pee in the shower?

It catches them off guard and gets oddly intimate. Plus, if you’re both cool with it, disgusting things can be some of the most funny things to talk about on a date.

15. What is the most embarrassing thing you’ve ever done?

It gets them to open up and be vulnerable.

16. What is the worst career idea you had when you were a kid?

It shows how they may have changed throughout their life. One of the most fun questions to ask on a date to get to lighten the mood.

17. What is your favorite and least favorite ice cream flavor?

Get to know their likes and dislikes. Plus, ice cream is always fun.

18. What color is your toothbrush?

A fun way to learn about their preferences, habits, and how attentive they are to the smaller details in life.

19. Would you rather spend a week at the beach or the mountains?

Helps you learn about what they like to do and where they feel most at home and alive.

20. If you were an animal, what animal would you be?

Their response to this question can show their personality and how creative they are.

Read: 82 Funny Bumble Bios That’ll Spark Conversation

21. Do you have any real-life superpowers?

This makes people think about their skills and talents. It gets them talking about something they take pride in.

22. What’s the weirdest nickname someone has ever called you?

See their weird side and ask how they got that nickname.

23. If you had to step in dog poo, would you rather step in it with your right or left foot?

As silly as it seems, it makes them think. See how practical they are.

24. What’s the weirdest place you ever went on a date?

A good conversation starter and a way to make them appreciate that the date you’re on now is a lot less weird that it could be.

25. Have you ever peed your pants in public and if so, what’s the story behind how that happened?

See if they can be vulnerable and that we can talk about stuff that’s not conventionally considered “appropriate.” Be bold and embrace cringeworthy topics to discuss on first dates.

26. Would you rather be Superman or Spiderman?

A good way to see what kind of skillset and persona they value. Both heroes have different backstories and compose themselves in different manners. Plus, you could get into a fun Marvel vs. DC debate.

27. What is your biggest kitchen fail?

See how they are in the kitchen and also see if they can joke about themselves. Failures in the kitchen are something we can all relate to from time to time.

Read: 38 Funny Tinder Openers That Actually Get Responses

28. What are the top 5 things you would take with you in a zombie outbreak?

See if they would grab random items or if they would select things that would actually be necessary. It can tell a lot about a person.

29. Did you have a funny nickname in high school/college?

Could reveal some secret backstory about them. Memories from school usually make for good first date conversation topics.

30. If your life were the “expectations vs reality” meme, what would the two pictures in the meme be?

It’s relatable and gets people thinking. It can show you how people think about their life.

31. What’s a lie you were told as a kid that you believed for way too long?

Takes them back to simpler times and might bring out some fun resentment in them toward whoever told them that lie. One of the best questions to ask on a first date because it’s playful and wholesome.

32. Which animal do you think makes for the best exotic pet?

Good barometer of their personality and quirks, and can lead the conversation in interesting directions.

33. If you won the lottery, what are the first three things you would do?

See how they handle money and what they value in life. Get an idea of whether they’re impulsive or more thoughtful, whether they think about the short-term or long-term, whether they’d spend the money on themselves or on others.

34. What was the craziest thing to ever happen to you on a date?

It’s fun to hear the dating stories of the person you’re with, and you can learn a lot about people from their past experiences.

35. If a theme song had to play every time you entered the room, which theme song would you choose?

This question could help you to assess my date’s perception of themselves and how they like to present themselves to others.

36. If you could reincarnate into any living creature, which creature would you choose and why?

Their answer could provide insight into their personality, quirks, and worldview.

37. Do you think there should be an expiration date on sour cream? What about blue cheese?

This gets them thinking and could make for a lighthearted debate.

Read: 54 Funny Tinder Bios to Get More Likes & Start Conversation

38. What is your go-to karaoke song?

May bring them back to a funny memory and a time when they felt special.

39. Would you rather fight a horse-sized duck or 100 duck-sized horses?

It’s a classic internet question, and it would show whether they have a good sense of humor and whether they think more logically or with intuition.

40. Which would you rather have as a pet: a dinosaur or a dragon?

It’s a random question that’s pretty out there. See what they do with it.

41. If you could steal one thing and get away with it, what would it be?

You’ll find out what they want most for themselves.

42. Which is better: pirates or ninjas?

This one’s for the millennials out there, to take things back to your youth and stir some nostalgic feelings.

43. What is your favorite poptart flavor?

Because it’s important to know if they have standards for quality food.

44. If you could be any mythical creature, what creature would you be?

Gets them using their imagination and stepping out of themselves for a moment to lighten up the mood.

45. What is the cheesiest pickup line you’ve ever used?

They might not have a good answer, and if that’s the case, then it could be fun to come up with some cheesy lines together on the spot. Try using them on each other.

Read: 15 Best Questions to Ask on Hinge (And Why They Work)

46. If you had to choose, would you rather live around mosquitos or spiders all day?

See how they think this one through to learn their tolerance for discomfort.

47. If you were an astronaut, what flavor of freeze-dried juice would you ask for to help you mask the taste of the water in space?

It makes people think outside the box and could show some of their personal taste and personality in a unique way.

48. What’s been your best Halloween costume?

Shows their creative side and gets them talking about something they take pride in (or something they’re embarrassed about).

49. What would your reaction be if we move in together one day and I randomly bring home a puppy?

Get a sense how spontaneous they are and if they’re an animal person.

50. What is your opinion on the dangerous chemical dihydrogen monoxide?

If they don’t know what it is, then they would be easily fooled by most scams (if you’re confused, then just Google “dihydrogen monoxide”… it’s the chemical name for water, folks).

Read: 80 Rizz Questions to Ask Your Crush

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

Get a glimpse into the inner weirdness of their mind. Good first date conversations often need a healthy dose of weirdness.

52. If you could be any character from a book, movie, or TV show who would you be?

You’ll get an idea what the they like when it comes to books and entertainment.

53. If you could trade lives with one person for an entire day, who would it be and why?

You’ll get to see what their ideal life would be.

54. If you could only listen to one song for the rest of your life, what would it be?

Shows their taste in music and their tolerance for repetition.

55. What’s a time in your life when you laughed so hard your stomach got sore?

Brings up something to share that makes people laugh or smile.

Read: How Often to Text After a First Date

56. If your coworkers had to make a sign letting everyone else in the office know not to let you do something, what would that something be?

It gives insight into what they’re like at work and what sort of relationship they have with people they see regularly.

57. Pancakes or waffles?

Because the silliest of questions can bring out the most passionate of debates.

Read: 101 Questions to Ask a Girl Over Text to Rizz Her Up

58. What’s your most unbelievable roommate story?

Because we’ve all been there…

59. What’s your wildest stories about a friend or coworker?

Can tell you about what type of people they surround themselves with. Plus, the stories are likely to be very funny and entertaining.

60. Would you rather be half shark or half koala bear?

Both of these animals are actually aggressive and strong. It’s just that koalas appear cuddly while sharks appear vicious. It would be interesting to see how they would want to be perceived.

61. What is your stance on pineapple on pizza, and how passionate are you about it?

This is just a silly question that everyone seems to have a firm and very strong opinion on. Knowing the answer now will help avoid fighting over the pizza order later in the relationship.

62. What would you do if we were the only people left on earth and we were surrounded by tiny cows?

It’s very outlandish and would hopefully get a laugh out of them.

63. If I were a worm (yes, a worm that can talk), would you still be interested in going on a date with me?

A good way to gauge their genuine interest in who you are on the inside.

64. Would you rather be a great white shark or a grizzly bear?

Shows how they connect with their aggressive side.

65. Can you say your ABCs backwards?

It’s actually quite difficult. See which one of you is worse at it!

Read: 101 Best Flirty Questions to Ask a Girl

66. What is an embarrassing moment you experienced at school growing up?

A great conversation starter and helps lightens the mood on a first date.

67. Would you rather go bungee jumping or skydiving?

Lets you know how adventurous they are (and maybe they’ll have a cool story to tell!)

68. What was the worst first date you’ve ever had?

Dating is hard, and nearly everybody can think of a time when a date didn’t go quite as planned or hoped for. Some of these experiences can be very funny looking back on them, so it could bring some lightness to the conversation and help settle the nerves.

69. If you could pick three celebrities to be a part of your entourage, who would you pick?

It’s a fun way to learn about someone and what their interests are, especially in television, movies, music, and other forms of pop culture. It’s also a good way to see what you have in common with someone.

70. If you could transform into anything in the world, what would you want to be?

It’s creative, the possibilities are endless, and it gives you a look into their imagination.

Read: 101 Best Flirty Questions to Ask a Guy

71. What’s one thing I definitely don’t know about you?

You can get such a wide variety of answers, some serious and some funny. You’re likely to learn about anything from their past experiences to weird talents to future ambitions.

72. What is your most obscure hobby?

You may find that they share the same obscure hobby as you, or that they can introduce you to something new and fun!

73. What’s the worst haircut you’ve ever had?

We’ve all had bad haircuts. This question can be joyfully embarrassing and help you bond over something unpleasant you’ve both probably experienced in your own unique way.

74. What is the ugliest car in your opinion?

A goofy question that can give you a good sense of the other person’s likes/dislikes and how much they value aesthetics.

75. So, how many times have you been around the sun?

It is a great non-offensive way to ask how old a person is.

Read: 5 Signs of Chemistry on a First Date: How to Know It Went Well

76. If you had to fight penguins, how many do you think you could take on at once?

A fantastical scenario that can lead to a funny healthy debate about how you would go about fighting the penguins.

77. If you could travel to any planet without the threat of death, which planet would it be and why?

A nonsensical question that’s sure to catch your date’s attention if they’re into science or philosophy.

78. Would you rather dance naked in front of coworkers or in front of your parents?

Because some playful cringe is always healthy on a first date. And, obviously, anything that gets your date thinking about being naked is one of the best things to talk about on a first date.

79. If you had to be any living species that’s not an animal, which species would you pick and why?

Most people ask this question about animals but not about other living organisms like plants, bacteria, viruses, etc.

80. If you could play only one game for the rest of your life, what game would you pick?

Gives you a better understanding of how they like to spend their free time.

81. Would you rather be a cat or a dog, and why?

It tells you a lot about their personality and is a way to assess personality compatibility. If they choose dog then I know they have a kind heart typically and are probably playful. If they choose a cat, then things get more interesting…

Read: 10 Reasons Why You Keep Having Bad First Dates

82. What is the weirdest flavor of ice cream you’ve ever eaten?

Shows if they’re adventurous. And who doesn’t like talking and thinking about ice cream?!

83. What is the craziest thing you have ever done?

Their response will tell you how adventurous they are, and depending on how crazy their story is, you might just figure out whether this person is your soul mate or worst nightmare.

84. If you had to pick one, would you rather wear socks or gloves every time you shower for the rest of your life?

It can really get them thinking, and it’s just an odd question to ask. Plus, you can see how much of a practical thinker they are depending on their answer.

85. What is something you did as a kid that you wish you could add to your adult routine, such as nap time?

A cute, funny question that makes them reflect on their childhood and simpler times.

86. On our next date, would you be down to come to the park with me and run around making bird noises together?

It would be funny and a fun activity to do together, that would definitely make for good stories later. See how eccentric they are.

87. Have you ever had a crush on a cartoon character?

This can give you a sense of what kind of person they’re attracted to without them having to choose a real-life person. It’s also funny to see what kind of cartoons they used to watch and think about romantically/sexually.

Read: When to Ask for a Second Date: How Long Should You Wait?

88. If we were on a deserted island, do you think you would eat me first or I would eat you first?

Their response can reveal what they think of you based on their first impression of you.

89. Would you rather have hot dogs for fingers or snails for toes?

It’s just a really weird question that’ll take their brain off of autopilot.

90. Which do you prefer: mice or snakes?

It’s an unexpected question, so the initial reaction will tell you more about them than the actual answer will.

91. How long did you believe in Santa Claus?

It’s light and gives a glimpse into their childhood.

92. What do you hoard?

It’s funny and you find out what strange interest they might have.

93. If you could be any age, what age would you pick?

Helps you understand their personality, what they value most, and what perspective they bring to their life.

Read: Which is the Best First Date? Coffee vs Drinks vs Dinner

94. Would you rather be stuck with hiccups or burping?

It could start a friendly debate, and also makes you appreciate that you’re neither hiccupping nor burping right now.

95. If you could be one cartoon character, who would you be and why?

Their answer could tell you what kind of ideal personality they identify with and fictional world they wish they lived in, which could tell you about what they value most in life.

96. What was your weirdest phase as a kid?

See how they laugh at themselves and reflect on what they used to be like.

97. What is your opinion on curly pigeons?

It’s funny and ridiculous, and it’ll probably lead you both to start looking up photos of curly pigeons on Google images together.

98. If you were stranded on an island and could only have three items, what would they be?

Tells how resourceful they are and what they value most in life.

99. If you had to shave your head, would you wear a wig or be bald?

Tells how much they value their appearance.

100. What is the most average thing about you?

We’re all a little average. Talking about our averages will spice things up because it’s not something we usually do on a first date.

Read: Texting Between the First and Second Date: 5 Rules to Know

101. If you could go back to college, what degree would you get purely for fun?

Tells you about what kinds of topics they find intrinsically joyful.

102. Do you like dogs or cats better, and why?

A classic debate that can tell you about their personality and lifestyle.

103. Would you rather have bionic legs or bionic arms?

It makes them think about what they value being able to do in life.

104. If you were a pizza topping, what would you be and why?

It has many different possibilities and is a creative way to think about food as a kind of personality or identity.

105. What is your spirit animal?

A fun one to get to know them. And if they don’t know their spirit animal, it could be a fun activity to take out one of your phones and take the quiz online together right then and there!

106. What is your favorite smell in the world?

Because scent is a powerful way to any person’s heart.

Read: 12 Tips for Having a Great Coffee Date

107. Can you fold a fitted sheet?

It’s important to know what skillset you could be getting out of this person in a relationship.

108. On a scale of 1-10, how good are you at parallel parking?

Whether they brag about their skills or laugh about their fails, it’s a fun one. If they’re not a good parallel parker, then ask them for funny stories about times they’re failed.

109. Is a hot dog a sandwich?

This is one of those questions that causes a lot of debate, but it can help you can find out if they share your sense of humor. And perhaps you agree on the answer and can bond over that.

110. What superpower would you not want to have, and why?

A good way to change up the more common question of asking which superpower someone would want to have. This’ll get them thinking.

Related articles:

15 Best Questions to Ask on Hinge (And Why They Work)

5 Signs of Chemistry on a First Date: How to Know It Went Well

7 Best Photos for Your Dating Profile

Which is the Best First Date? Coffee vs Drinks vs Dinner

When to Ask for a Second Date: How Long Should You Wait?

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