Think you know your friend like the back of your hand? Think again! All of us tend to carefully omit the parts that we’re too embarrassed or shy to say out loud. But things don’t have to stay that way! Let’s be honest — nothing loosens one’s tongue more than being drunk. And that’s when you can ask all the questions you always wanted to ask your friends.
So, whether you’ve just made a new friend or are looking to forge a deeper bond with your best buds, these questions to ask drunk friends that are guaranteed to unearth secrets!
99 Questions to Ask Drunk Friends
#1. Have you ever had a one-night stand?
#2. What was the dumbest thing you’ve ever done?
#3. What is the grossest thing you’ve done that you would be grossed out by if someone else did?
#4. What’s the biggest age difference you’ve had between yourself and a sexual partner?
#5. Have you ever shoplifted?
#6. What’s the #1 thing you never want your parents to find out about you?
#7. What’s the riskiest thing you’ve ever done?
#8. What’s the most adventurous thing you’ve ever done?
#9. What’s something you’ve done while drunk that you would never do sober?
#10. What’s the least amount of time you’ve known someone before sleeping with them?
#11. What’s the worst date you’ve ever had?
#12. What’s the longest you’ve gone without showering?
#13. Have you ever sneaked out?
#14. When was the last time you wet your bed?
#15. What’s your biggest dating horror story?
#16. Have you ever done something naughty with a teacher?
#17. Have you ever told someone you wouldn’t be home just so they wouldn’t come over to yours?
#18. What’s something we’d be surprised to know about you?
#19. What’s the biggest secret you’ve spilled because you’ve gotten so drunk?
#20. What is the craziest thing that has happened to you in a public place?
#21. Have you ever bought something to wear to an event and then returned it to the store when the event was over?
#22. Ever had a “friends with benefits” situation?
#23. What is your guiltiest pleasure even your closest friend doesn’t know about you?
#24. Have you ever fancied a cartoon character? If so, who and why?
#25. What would you do if one of your friends started dating your ex?
#26. Have you ever bribed or flirted with a police officer to get out of a ticket?
#27. What’s the most illegal thing you’ve ever done?
#28. Have you intentionally sabotaged your relationship?
#29. Have you ever been skinny dipping?
#30. Have you ever roleplayed in bed?
#31. What do you like to be called in bed?
#32. What was the most embarrassing thing you ever did while on a date?
#33. Have you ever ghosted anyone? If so, why?
#34. What’s the most outrageous thing you’ve ever done for love?
#35. Did you ever blame someone else for your farts? How did that turn out?
#36. Who’s the most scandalous person you’ve had sex with?
#37. Have you ever accidentally sent an inappropriate text to a family member?
#38. What is the most broke thing you’ve ever done?
#39. What’s the closest you’ve ever come to cheating?
#40. Have you ever accidentally seen someone in their birthday suit?
#41. Have you ever been in a secret relationship?
#42. How adventurous are you in the bedroom on a scale of 1 to 10?
#43. How far have you gone in public?
#44. Ever sneaked someone into your house?
#45. What’s your most outrageous sexual fantasy?
#46. What’s the most embarrassing thing you’ve ever done to get back with an ex?
#47. What’s the most spontaneous thing you’ve done?
#48. Have you ever fallen asleep during sex?
#49. Has anyone ever caught you in the act?
#50. Have you ever sexted?
#51. What’s the kinkiest thing you’ve ever done?
#52. What’s the dirtiest text you’ve ever received?
#53. Have you ever hooked up with someone you shouldn’t have?
#54. Have you ever asked someone to take a dirty photo of themselves?
#55. Have you ever lied to your partner, saying you feel sick, to avoid an intimate moment?
#56. What’s the raunchiest dream you’ve ever had?
#57. Have you ever faked an orgasm with someone just to get it over with?
#58. Have you ever sent nudes to someone?
#59. Have you ever gone on a date with two people on the same day?
#60. What’s your biggest dating disaster?
#61. Have you ever hooked up with someone you didn’t know?
#62. What do you think is your hidden talent between the sheets?
#63. What was the most awkward thing that happened to you during sex?
#64. Have you ever thought of someone else while you were sleeping with someone?
#65. Have you ever had sex with someone of the same sex?
#66. What’s the first thing you would do if you woke up one day as the opposite sex?
#67. What secret conspiracy would you like to start?
#68. Have you ever paid for adult content?
#69. Would you ever date someone of the same gender?
#70. What’s the strangest thing someone would find in your search history?
#71. What’s the most disgusting habit you have?
#72. Do you ever talk on the phone while you’re taking a poop?
#73. What is a rumor/gossip you repeated about someone but found out was incorrect?
#74. What is a silly thing you are emotionally attached to?
#75. Have you ever slept with someone you met online?
#76. What was your most embarrassing sexual experience?
#77. What is your favorite compliment to receive?
#78. What’s the craziest dream you’ve ever had?
#79. What do you wear when you’re hoping to go home with someone?
#80. What is the strangest thing you have ever bought?
#81. Have you ever woken up somewhere you don’t recognize after a night out?
#82. Do you believe aliens are real?
#83. Have you ever slept with someone and then immediately regretted it?
#84. Have you ever danced on a table when you were drunk?
#85. What is the shallowest reason you used to get out of a second date?
#86. What’s the worst pickup line you’ve ever heard on a night out?
#87. Have you ever filmed yourself having sex?
#88. Have you ever ditched someone on the first date? Why?
#89. Have you ever purposely flirted with a friend to make their girlfriend/boyfriend jealous of your friendship?
#90. What’s the weirdest roleplay you’ve ever done?
#91. Have you ever been caught masturbating?
#92. Where is the worst place you’ve ever kissed a date?
#93. What was the most embarrassing time you got turned on?
#94. Have you ever hit on a barman/barmaid while drunk? Were you successful?
#95. Did you ever break up with someone just before a public holiday so that you didn’t have to buy them a gift?
#96. Have you ever walked in on your parents doing it?
#97. Have you ever farted while spooning with someone?
#98. What’s the worst thing you’ve ever done at work?
#99. What’s the wildest sex position you’ve ever tried?
