Skip to Content

150 Embarrassing Questions To Ask Friends For Awkward Conversations

A photo of Tom who is the Co-Founder of Questions About Everything

To learn how this content was created please read our Editorial Guidelines.

If you want to make your friends squirm, these embarrassing questions to ask are perfect.

We all have moments in our lives that made us cringe. It could be a wardrobe malfunction, something that happened at school, or something our parents caught us doing.

These most awkward questions will make you relive those moments, and make for some funny and interesting conversations!

Ask these uncomfortable questions and watch your friend’s faces contort with agony as they relive some of their most embarrassing truths!

Affiliate Disclosure: Thank you for supporting us. When you purchase through links on this site, we may earn an affiliate commission. Please see our Advertising Disclosure for more details.

Best Embarrassing Questions

1. What’s the most embarrassing thing in your search history?

2. What’s the most embarrassing thing your parents have caught you doing?

3. What’s the most embarrassing thing you’ve said in front of someone you liked?

4. Would you rather be caught picking your nose or scratching your bum?

5. Has your girlfriend/boyfriend ever embarrassed you in front of all your friends?

6. Have you ever been caught masturbating by your parents?

7. Have you ever farted so loud in class everyone heard?

8. Have you ever sent a dirty text message to the wrong person?

9. What was the most embarrassing thing to happen to you at school?

10. What’s the biggest secret you’ve ever kept from your parents?

11. Have you ever had a wardrobe malfunction in public?

12. What’s the most embarrassing experience you’ve had with a crush?

13. What’s the weirdest thing that’s turned you on?

14. How old were you when you stopped sleeping with stuffed animals?

15. Have you ever waved at someone thinking they were someone you knew, only to realize you didn’t know them?

16. Have you ever practiced kissing in front of the mirror?

17. If you could erase one past experience, what would it be?

18. What children’s movie do you secretly love?

Make It A Night With Friends To Remember With One Of These Awesome Games (Available on Amazon

Games To Play With Friends You Might Love (Available On Amazon):

You might also like: Interesting Conversation Topics

19. What was the most embarrassing thing to happen while you were on a date?

20. Are you a virgin?

21. Have you ever walked into a wall or a streetlight?

22. Who’s one person you pretend to like but actually don’t?

23. If you had to hook up with one of your friend’s partners, who would you choose?

24. Do you sing in the shower?

25. What’s the longest amount of time between you dropping something on the floor and picking it up to eat?

26. Have you ever had someone walk in on you when you were on the toilet?

27. Have you ever accidentally hit something while driving?

28. How often do you wash your underwear?

29. Have you ever been caught checking someone out?

30. Have you ever posted something on social media you later regretted?

You might also like:

Embarrassing Questions To Ask A Guy

31. What’s the worst smell you’ve ever smelt?

32. What part of your body do you wish you could change?

33. Have you ever had a man crush?

34. What’s the most creative insult you can come up with?

35. Do you enjoy having a beer belly?

36. Can I give you a makeover?

embarrassing questions makeover

Next: Random Questions to Ask a Guy

37. Have you ever had an STD?

38. Have you ever lied to me?

39. Do your work colleagues/friends have any nicknames for you?

40. What’s the most embarrassing moment to happen to you in public?

41. Have you ever taken a sexy picture of yourself?

42. What was the strangest thing you liked to eat as a child?

43. How many girls have you had sex with?

44. What score would you give me out of 10?

45. If you held a world record for something, what would it be for and why?

46. Do you talk in your sleep?

47. What’s your idea of the perfect first date?

48. What’s the worst thing you’ve done for love?

49. How many weeks could you last without your cell phone?

50. What video game would you most like to be transported into?

51. What’s your biggest fashion faux pas?

52. Have you ever tasted ear wax?

53. If you had to tell one joke to save your life, what joke would it be?

54. What’s the dirtiest thought you’ve ever had?

You Might Also Like: Open-ended questions or Topics to talk about

embarrassing questions dirty thoughts

You might also like: Juicy questions

55. What’s one app you couldn’t live with?

56. What has been the biggest waste of money you’ve spent?

57. What’s your favorite rom-com movie?

58. What would be your best weekend getaway?

59. What’s your worst secret?

60. Have you ever drooled in your sleep?

Are You Hanging Out With Friends? Check out this collection of fun things to do with friends from Cosmopolitan!

Embarrassing Questions To Ask A Girl

61. Have you ever fancied a waiter?

62. Do you have smelly feet?

63. What is the most embarrassing chat-up line you’ve heard?

64. Have you stalked a crush on social media?

65. Who’s your favorite out of your mom and dad?

66. What’s the most embarrassing thing your friends have done while you’ve been there?

67. What’s the largest amount of money you’ve spent on online shopping?

68. Have you ever farted during a sports class?

69. Have you ever been to the toilet in nature?

70. When did you last shave?

71. Have you ever visited a strip club?

72. Have you ever flirted with your boyfriend’s friends?

embarrassing questions flirted with a friend of your boyfriend

You might also like: Flirty questions to ask a girl

73. Have you ever tried or been tempted to try a drug?

74. What’s your most embarrassing drunken moment?

75. Have you ever lied about your age?

76. Have you ever pretended to be someone famous in front of the mirror?

77. Have you ever pretended you liked someone’s outfit when you really didn’t?

78. Have you ever had a crush on a teacher?

79. Have you ever sent a nude picture of yourself to someone you didn’t mean to?

80. What’s the most embarrassing work moment you’ve had?

Funny Embarrassing Questions

81. Describe your perfect boy/girl to me?

82. Who’s the sexiest person in the room right now?

83. Have you ever been caught checking out someone else?

84. Have you ever peed in the bath?

85. What’s the most amount of burgers have you eaten in one sitting?

86. What would your porn star name be?

87. Do you ever dance when you’re in the house alone?

88. Have you ever pretended to be on the phone when you don’t want to speak to a charity worker?

89. What do your favorite pyjamas look like?

90. Have you ever been tempted to buy something useless off the shopping channel?

embarrassing questions tv shopping

You might also like: Have you ever questions

91. Do you have a favorite cuddly toy?

92. Have you ever picked food up off the floor and put it on someone’s plate?

93. Have you ever used a tan enhancer?

94. Have you ever pooped your pants?

95. What has been the most embarrassing injury you’ve had?

96. Do you write a diary?

97. Have you ever had lice in your hair?

98. What’s the most embarrassing piercing you have?

99. Do you speak to your pet as if they were human?

100. What’s the best way to hold your farts in public?

101. How often do you change your sheets?

102. Have you ever wanted more than one boyfriend/girlfriend at a time?

103. Have you ever cheated while playing a game with your friends?

104. Have you ever seen your grandparents naked?

105. Have you ever accidentally injured someone?

106. Have you been in trouble with the law before?

107. What age do you think I am?

108. How did you break up with your last partner?

embarrassing questions how did you dump your ex

Next: Random questions to ask

109. Am I the best lover you’ve been with?

110. Have you ever called me your ex’s name?

111. Who’s more important, your Mom or me?

112. Would you ditch all of your friends to be with me?

113. What’s the worst meal anyone has ever made for you?

114. What would be your karaoke song? Can you give me a sample now?

115. Has a loved one ever missed a special occasion of yours?

116. Have you recently gained weight?

117. Would you ever talk about me behind my back?

118. Do you always wash your hands after you’ve been to the bathroom?

119. If you had to make out with any Disney character, who would it be?

120. Have you ever had terrible breath?

121. Why do you chew so loudly?

123. Do you still watch cartoons?

124. Have you cried at a Disney film?

125. Have you ever drunk texted someone?

126. Have you ever told someone you loved them but didn’t really mean it?

embarrassing questions told someone you loved them but didn't mean it

You might also like: Deep conversation starters

127. How much money does your job pay?

128. What are you most self-conscious about?

129. Have you ever dressed as the opposite sex?

130. Have you ever starred in an amateur adult movie?

131. What random piece of home furniture could you not live without?

132. Do you still take bubble baths?

133. Who would you say are more attractive, people from the USA or people from Europe?

134. If you had to describe your positives and negatives, what would they be?

135. What game do you always get competitive playing?

136. What’s the most expensive thing you’ve ever broken?

137. If your life was a movie, what part would the audience cringe at?

138. Would you ever consider sleeping with your brother/sister’s exes?

139. Have you ever walked out of a film at the cinema?

140. If you ran your own country, what would you call it and what title would you give yourself?

141. If you had to pick a celebrity hairstyle to copy, who would you choose?

142. Have you ever said something no one else found funny? If so what was it?

143. What’s the craziest idea you’ve ever had?

144. Do you ever find yourself counting your steps? If so, what’s the most you’ve ever done?

145. What’s something that I would never guess about you?

146. What’s your strangest bug-related story?

147. What piece of clothing do people think makes them look super cool, but it actually looks terrible?

148. What’s the cheesiest thing you’ve said to someone?

149. What’s your worst roommate/housemate story?

150. Have ever ripped clothing in an awkward place while you’ve been out in public?

Looking For More Questions?

Never have I ever questions – Another list of questions that will lead to some embarrassing conversations.

Yes or no questions – Quick questions with an even quicker answer. This will lead to a fun conversation no matter who you ask them to.

Disclosure: Thank you for supporting Questions About Everything. Some of the links in this article may be affiliate links, meaning I may earn a commission if you make a purchase Please note this is at no additional cost to you.

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.