Embarrassing Yes or No Questions to Ask Anyone

In search of some exciting topics to discuss with loved ones? Start a conversation starter game by asking embarrassing yes or no questions.

Use silly, unusual questions as conversation starters, and challenge or pry into your partner’s space. As with other tried-and-true question games like “Truth or Dare,” there is no “wrong” answer to a well-crafted Yes/No question.

This article has you covered on the best embarrassing questions you could want to ask anyone. Read on!

Photo by Towfiqu barbhuiya on Unsplash

Hilarious Yes/No Questions

Try posing these humorous Yes/No questions for some laugh-out-loud moments with loved ones. 

  • Are you capable of pulling off complex practical jokes?
  • How well can you drive?
  • Do you remember ever sleepwalking?
  • Does your eyebrows wiggle?
  • Have any experience with eating competitions?
  • Can you open your eyes while sneezing?
  • Do you recall a time when exhaustion rendered you delirious?
  • Have you ever tried to fly?
  • Do you have a best friend?
  • Do you ever over eat?

Interesting Yes/No Questions

These are some embarrassing questions you might hear from your date, co-workers, or friend. Using these questions can start up some fun conversations with people!

  • To what extent does one’s sense of humor limit one’s bladder?
  • Have you found that people never fail to laugh at your jokes?
  • What about inanimate objects: Have any of those ever given you a fright?
  • Could you force a burp out of yourself?
  • Can you ever be friends with a friend’s enemy?
  • When last did you do something for fun?

Random Embarrassing Yes or No Questions

Strange or seemingly irrelevant inquiries can often stimulate conversation. You can use these as a jumping-off point to create unique and interesting questions to test your pals.

  • Is your pet privy to all of your secrets?
  • In what circumstances might you seek out fame
  • Any swimming skills?
  • How well versed are you in the game of poker?
  • Can you recall any times when you were featured on television?
  • How often do you floss?
  • How did you get to know how to drive?

Great Yes/No Questions

Everyone enjoys being able to ask a personalized question that they can relate to. At the end of the day, no one can resist learning more about someone and this guessing game is one way to do that.

  • How about skiing?
  • Do you know the names of any constellations?
  • Are you a runner?
  • What’s it like to go viral?
  • Does anyone here know how to moonwalk?
  • Do you know the capital of each of the 50 states in the United States?

Juicy Yes/No Questions to Explore

Everyone likes having a little bit of sweet gossip with their conversation. These are great to have on hand for sleepovers and lengthy car rides.

  • Is there someone you’re crushing on?
  • How about if I offered you $100 to dance in public for 10 minutes without music?
  • Could you describe a time when you “ghosted” someone?
  • How often do you spread false information?
  • When was the first time you were caught lying?
  • How often do you get asked out on dates?

Excellent Ice Breaker Yes/No Questions

Asking someone simple yes/no questions is an excellent way to ease the tension when getting to know someone. Even if they aren’t ready to open up about their lives, you can learn more about them by asking them lighthearted trivia questions. Here are some questions to ask:

  • On a scale of 1-10, how much of an introvert are you?
  • Does watching scary flicks make you happy?
  • To what extent do you enjoy dining out?
  • Are you an international traveler? If so, how often?
  • Are you an early bird?
  • Is city life something you’re interested in?
  • Is pizza with pineapple a favorite of yours?

Easy Yes/No Questions to Explore

The questions to ask someone might be so basic and simple, but you will get a lot of surprising answers from them. Be careful not to judge someone based on their answer because they are just being honest. Allow them to share their opinions. Some answers may be no, and that’s okay. 

  • Does music help you fall asleep?
  • Any musical abilities?
  • What recent movies have you seen that you enjoyed?
  • Are you a sports fan?
  • Where did your ancestors come from?
  • How about famous people?
  • Does coffee play a regular role in your daily routine?
  • How about skydiving?
  • Have you discovered any of your hidden abilities?


If you need a way to connect with people, you should ask questions that quickly bring to light your shared interests. Embarrassing yes or no questions could be particularly effective as they’re universally amusing.

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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