138 Funny Questions to Ask on a First Date

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So, you’ve finally got a first date with someone you’re interested in? Congrats!

But before you start imagining your future together, let’s be honest- first dates can be awkward and nerve-wracking. 

Fortunately, we’ve got just the thing to break the ice and have some laughs.

Forget about the boring, generic inquiries that everyone asks, and get ready for some playful banter that will have you and your date grinning from ear to ear. 

Our list of funny questions to ask on a first date will not only help you get to know your date better but will also keep the conversation flowing and light-hearted.

Who knows, you might even discover some surprising things about your special someone that you never would have expected. 

So, sit back, relax, and get ready to inject some fun and laughter into your first date!

You may also like our list of date night questions and romantic questions for couples.

Funny First Date Questions About Growing Up

Ready to share your funny experiences and memories from childhood on a date?

These hilarious first date questions about growing up are sure to get you both reminiscing and giggling in no time!

1. If you could go back in time and give your younger self some hilarious guidance, what would it be?

2. What was your favorite candy as a kid?

3. What was your favorite meal as a kid that you’d never eat as an adult?

4. What kind of games did you play with your friends?

5. What job did you want to have when you grew up as a kid that is laughable now?

6. Did you have a crush on a cartoon character growing up?

7. What is something weird that you did as a child?

8. Were you picked first for the team?

9. What was the first TV show you watched that you knew you weren’t allowed to?

10. Did you have an imaginary friend?

11. Have you secretly or overtly laughed at people from school’s grown up misfortunes?

12. Tell me a funny fact or story about where you grew up.

13. Did you have any embarrassing habits?

14. Did you ever perform in a talent show, if yes, what was your talent?

15. What traits from your parents do you now see in your or your siblings?

16. How did you spend your summer vacations and how did you want to spend your summer vacations?

17. Describe the wackiest fashion trends you followed.

18. What is a funny high school memory involving a teacher?

19. What is the weirdest thing you ate as a kid?

20. Have you recently learned that something you believed to be true as a child was not true at all?

21. What memes make you laugh?

22. What is the weirdest thing a grandparent ever said to you?

23. Which celebrity did you have hanging on your bedroom wall when you were a teenager?

24. What was an obsession of yours that you still secretly love?

25. Did you learn how to perform magic tricks? Show me!

26. Which TV show character did you want to be?

27. Do you still have any stuffed animals from your childhood?

28. Is there a food from your childhood that you ate so much that the thought of it makes you feel sick now?

Pair these funny things to talk about on a date with our list of this or that questions for adults.

Afternoon tea treats

Funny First Date Questions About Family and Friends

Let’s face it, talking about family and friends on a date can be a snooze-fest.

That’s why we’ve rounded up the following fun questions to ask on a first date to keep the conversation lively and entertaining!

29. Do you play pranks on your friends and family? If yes, what is the best prank you have pulled off?

30. Have your friends ever hired a clown for a party?

31. What have you blamed on a sibling or friend to avoid getting into trouble?

32. Where is somewhere you would like to go with your friends for a weekend of laughs?

33. What is an activity that you really want to try but you can’t get your friends to join you?

34. What is the dumbest dare you have ever done?

35. Do you share your streaming log-ins with your friends or family or do you stick to the rules?

36. Have your parents ever embarrassed you while you were on a date?

37. Have you gone on a blind date set up by a friend before?

38. How would your friends describe you in three words beginning with L?

39. If I were to meet your friends do I need to know anything funny that they might share beforehand?

40. Who is the last friend you screened and why?

41. Have you ever set up a friend who didn’t want set up?

42. Have you fallen and your friends have laughed so much they couldn’t help you?

43. Tell me an ‘in’ joke only your family laugh at.

44. What kind of memes do you share with friends?

45. Do you have any friends that don’t laugh at all?

46. What is a family tradition that your family has that you don’t like?

47. Do you have a family reunion every year? If so, share a funny story.

48. What is the wildest thing you and your friends have done?

49. Have you had a paranormal experience with your friends?

50. What word, slogan, or saying is guarteneed to make your friends laugh?

51. Has a dinner party ever gone wrong? Spill!

52. Do you and your friends still dress up for Halloween?

53. Do you prefer to host Super Bowl parties or attend Super Bowl parties?

54. Have you clogged a toilet at a friend’s house?

55. If you had to ditch one sibling or friend who would it be and why?

56. Do you friends prefer dark humor or splapstick laughs?

Prepare for your second date with our list of questions that will spark interesting conversations.

Two senior friends sitting at a cafe laughing and talking.

Funny Questions About Dating History

Forget the boring small talk and dive into some silly first date questions about each other’s dating history that will have you both rolling with laughter. 

You never know what kind of interesting stories you might uncover!

57. What is the worst date you’ve ever been on?

58. Have you been broken up with over a text message?

59. Do you have a deal breaker that others may find odd?

60. Have you bailed on a date before it was over?

61. Are you still friends with an ex but really shouldn’t be?

62. What is your idea of a fun date?

63. Has a date done anything disastrous?

64. Do you have any funny speed dating stories?

65. Have you lied on dating profiles before?

66. What about while messing a potential date?

67. Have you had a friend call you with an emergency to get out of a bad date?

68. Where is the scummiest place you have gone on a date?

69. What is a pickup line that someone used on you, and it worked?

70. Have you ever gone on a date out of pity?

71. Do you have a funny first date story?

72. Did you ever have a date canceled on you?

73. Where is the strangest place you have had a date?

74. Have you been out on a date with someone who showed up wearing something really bizarre?

75. Have you ever been on a date so horrible you would rather set yourself on fire than finish the date up?

76. Would you prefer to date someone much richer or less wealthy than you?

77. Have you been out on a date with someone significantly taller than you?

78. What is the weirdest thing someone you were on a date with ordered at a restaurant?

You may also like our list of open ended questions.

Happy couple having drinks together by the beach.

Funny First Date Questions About Work

Everyone has funny and cringe-worthy work stories that are just begging to be shared.

Get ready to laugh, learn, and maybe even fall in love over some hilarious work-related questions to ask on your first date.

79. What is the worst job you have ever had?

80. What animal represents your personality in your workplace?

81. What would you never wear to work and why?

82. Do you do a number two at work?

83. What is something funny that happened during a Zoom meeting and Zoom game?

84. If you could compare your job to a TV show which show would that be?

85. What is something you enjoy that you wish you could get paid for?

86. Have you gotten drunk while at work?

87. What is your fantasy job title?

88. Have you been in a physical fight while at work?

89. Have you ever quit out of anger?

90. Have you ever told your boss off?

91. Have you ever done something you regret in front of coworkers outside of the workplace?

92. What is the most clever Wi-Fi name you have seen?

93. What is the most outrageous thing you have done to make money?

94. Have you ever pretended to be doing something busily when your boss is watching?

95. If you could learn one useless skill within a few hours, what would it be?

96. If you could have any career in the world, what would it be? The catch? It has to make very little money.

97. What really grinds your gears about the office?

98. Has anyone stolen your lunch or have you ever helped yourself to someone’s?

Hands typing on a laptop.

Funny First Date Questions to Ask a Man

Landed a date with a guy who has the potential to be ‘’the one’’, and wondering how to get the conversation rolling?

We’ve got you covered with these funny date night questions to ask a man that will not only help you connect with your date but also ensure a good time! 

99. How clean is your house right now?

100. When did you last shower?

101. What is something that you’re afraid of that you are embarrassed about?

102. Have you ever been caught sneaking a midnight snack?

103. What is something that women wear that makes you cringe?

104. Tell me your best night out drinking story.

105. Have you ended up in the drunk tank for a night?

106. What is the longest amount of time you would leave food on the floor before picking it up and eating it?

107. Do you do impressions of anybody? Show me!

108. If we were to go to karaoke tonight, would you sing and what song? Here’s a list of duets for ideas.

109. Are you brave enough to put your hair on the line for a thousand bucks and let the worst-rated barber in town have their way with it?

110. What is the craziest thing you have done for a partner?

111. How many days do you wear a pair of jeans before you wash them?

112. How many cupcakes can you eat in one sitting?

113. Have you used an Ouija board, what happened if you have?

114. What is the most hilarious thing that has happened to you this week?

115. What do you dislike the most about first dates?

116. What do you keep in the trunk of your car?

117. If you were to give a TED-style talk, what would you talk about?

Male entertainer standing on stage.

Funny First Date Questions to Ask a Woman

Looking for funny first date conversation starters with your special lady? 

Let’s dive into some lighthearted chit-chat with the following questions and get ready to ignite some playful banter and maybe even spark a little romance!

118. Do you have any exotic pets?

119. Did you buy a bunch of plants during the pandemic?

120. For a thousand bucks, will you put on full-face makeup using mall testers?

121. If you could be invisible for the day, what would you do?

122. If you had your own daytime talk show who would your first guest be?

123. Do you talk to your pets?

124. What is the biggest word you know?

125. How often do you wash your hair?

126. How many salted crackers do you think you can fit in your mouth at once?

127. What is the craziest thing you have done for a friend?

128. How clean is your car right now?

129. Would you prefer to walk around a haunted house or ride a roller coaster?

130. How long do you believe you could go without your phone?

131. What is a subject you could talk about for hours and not get bored?

132. What is a funny cooking mishap you have had?

133. Have you clogged a toilet at work?

134. If you won a thousand dollars today, what would you buy that would make me laugh?

135. What is something stupid that you have done to impress someone?

136. Have you sent drunk texts? Tell me about them if so.

137. Have you sent a text to someone that you were complaining about by accident?

138. What is the lamest joke you have ever heard?

You may also like our list of questions for this or that, never have I ever, yes or no, and would you rather– all designed for girls.

Young woman covering her mouth while smiling with food on the table.

Final Thoughts

Well, there you have it- a list of funny and playful questions to liven up your first date! 

If any of these questions lead to a memorable moment on your date- let us know in the comments below.

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