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New Study Reveals 110 Best Funny First Date Questions to Ask

It can be challenging to know what to talk about on a first date.

First dates can be awkward, and most first date tips out there don’t seem to help that much. We’ve all been there, on a boring first date that feels like an interview—or worse, a first date where neither of you can even think of any questions to ask each other.


Good conversation makes for a good first date. No matter what over-the-top extravaganza or what low-key first date ideas you’re thinking of going with, it’s important to ask the right questions on your date so you can get the conversation flowing. And if you want to make sure you spark connection and create chemistry, it’s even more important to share a few laughs.

Asking funny questions on the first date can ensure that you both have a good time, get to know each other, and have a second date lined up ahead.

What funny questions are best to ask on a first date?

We at The Match Lab conducted a new study to discover the best funny first date questions. We surveyed 50 people from across the United States and asked them what they think are the best first date questions that’ll get a laugh. All in all, our study revealed 110 questions.

Get ready to fill up on good first date questions. With this list in your back pocket, you’ll never run out things to talk about on a first date again.


Without further ado, here are the 110 best 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!

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.

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.

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.

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.

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.

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).

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.

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.

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.