60 Most Embarrassing Questions for Friends

Embarrassing questions for friends are an excellent way to have good laughs and engaging discussions. There are humiliating times in everyone’s past. 

It may be an embarrassing wardrobe malfunction, an incident at school, or a transgression our parents discovered and dealt with.

Make your friends suffer through the anguish of remembering their most shameful moments by asking probing questions. You may find the questions below shocking and risky, but they are guaranteed to create a lighthearted mood.

Photo by Duy Pham on Unsplash

Best Embarrassing Questions for Friends

These questions are crazy and unique enough that you should have no problem embarrassing your friends. 

  • What’s the worst thing you’ve ever said in front of a person you cared about? 
  • To be caught nose-picking or behind-the-back scratching? 
  • Can you think of a time when your boyfriend or girlfriend made you feel bad in front of a group of people? 
  • Have your parents ever caught you masturbating? 
  • When it comes to your parents, what is the biggest secret you’ve ever kept? 
  • Have you ever let one out in class that everyone could hear? 
  • Tell me about a mortifying item in your internet history. 
  • Have you ever accidentally sent a sexist or racist text? 
  • Tell me about a mortifying moment you experienced while attending school. 

Wild Embarrassing Questions to Explore With a Partner

Want to go dirty and nuts with a partner? Try these wild embarrassing questions for free.

  • Do you recall ever having a public wardrobe malfunction? 
  • Tell me about the time you did something idiotic in front of your crush. 
  • How about the most out-there thing that has ever gotten you horny? 
  • When did you stop using a teddy bear or other stuffed animal as a pillow? 
  • Have you ever waved at a person you thought you knew, only to find out later that you were mistaken? 
  • How about practicing your kisses in front of a mirror? 
  • What would you choose to forget if you had that option? 
  • Which animated film did you enjoy as a kid that you now hate watching with your kids? 
  • Can you think of the mortifying moment that occurred on a date? 
  • Would you say that you’ve never had a boyfriend before?

Embarrassing Questions That Would Make You Smile

These questions are pokey, engaging, and maybe even a bit embarrassing for those asking them and those answering. 

  • How often do you bump into things like walls and streetlights? 
  • Just one person you say you like but don’t. 
  • Whose partner would you pick if you had to sleep with someone in your friend group? 
  • How often do you find yourself singing in the bathroom or while you’re washing your hair?
  •  How long does it take the average person to realize they’ve dropped food on the floor before picking it up? 
  • When was the last time someone walked in on you while using the restroom? 
  •  Have you ever accidentally hit something with your car? 
  • Could you tell me how often you wash your underwear? 
  • When was the last time you were caught conducting a casual sexting session? 
  • Have you ever made a social media post that you regretted deeply?

Embarrassing Questions Related to Guys

As friends, partners, or family, it’s fun to pose embarrassing questions once in a while to get a good jolt of laughter. Let’s try out some awkward, uncomfortable questions to see how often they work!

  • Discuss the most repulsive odor you’ve ever encountered. 
  • What physical trait do you wish you could alter? 
  • Do you remember the first time you had a crush on a man? 
  • What’s the most original put-down you can think of? 
  • Does a beer belly bring you joy? 
  • Would you let me give you a new look? Are you STD-free? Tell the truth; when was the last time you lied to me? 
  • Is there a name by which people at work or in your social circle call you?
  • Tell me about the most socially awkward experience you’ve ever had.

Deep Embarrassing Questions for Adults

Embarrassing questions are a universal concept that many people get very uncomfortable with. It can be challenging to understand how someone could ask something so personal of you. But asking someone embarrassing questions is something that can bring people closer together.

  • When was the last time you took a hot photo of yourself? 
  • As a kid, did you have any unusual food preferences? 
  • You’ve had sex with how many females? 
  • How many points would you give me? 
  • Why would you want to hold a world record for whatever it is that you currently don’t? 
  • When you sleep, do you ramble on? 
  • Is there a particular type of first date that has always stood out in your mind as the ideal? 
  • Where have you gone to extremes for the one you love? 
  • How long, in weeks, could you go without your cell phone?
  •  Which video game do you despise the most?

Embarrassing Questions to Try for Fun

These questions are perfect for couples, friends, and family members. They will help everyone to explore the intimate aspects of their relationships and laugh about how awkward it can be to talk about them.

  • What is the worst fashion mistake you’ve ever made? 
  • Please describe the taste of ear wax if you’ve tasted it. 
  • For your survival, what joke would you tell? 
  • Give us an example of your most vile mental image. 
  • How about the one app you can’t seem to function without? 
  • Let us know about the most egregious financial misstep you’ve ever made. If you had to pick just one, what would it be? 
  • Where would you most like to go for a weekend excursion? 
  • What is it that you’re keeping from the world that you wish you weren’t? 
  • Do you snore or drool while you sleep?


Embarrassing questions for friends and partners set the tone for exciting conversations. Sometimes it could be to break the ice or to have a good laugh. Whatever the case, it’s always better to have laughter at your expense than at the expense of others. 

Abir is a data analyst and researcher. Among her interests are artificial intelligence, machine learning, and natural language processing. As a humanitarian and educator, she actively supports women in tech and promotes diversity.

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