47 Embarrassing Questions to Ask a Guy

Heather Long
Contributor: Michele Meleen
Embarrassed guy

Embarrassing questions to ask a guy are very subjective. What may embarrass one person may not embarrass another. However, deeply emotional or intimately probing questions can be embarrassing for both of you if you're not at the right relationship stage to discuss them.

Awkward Questions to Ask any Guy

While some questions are embarrassing for you to ask and some questions are embarrassing for the guy to answer, you may want to know the answers to these questions, particularly when they are about commitment, emotions, and the longevity of the relationship. However, asking them directly may not be the best plan.

  • When was the last time you cried?
  • Guess how many guys I've slept with?
  • Have you ever seen your mom/sister/grandma naked?
  • Are you sure you're not gay?
  • Do you like having a beer belly?
  • How long does it take you to get ready for a date?
  • How many girls' numbers are in your phone?
  • Can I give you a makeover?
  • How much debt do you have?
  • Have you ever considered plastic surgery?

Pushing the Envelope

The most embarrassing questions are those that push the envelope of taste and decorum. The more you press someone for an answer, particularly one he or she may not want to give, the more likely you are to embarrass one or both of you.

  • Have you ever killed or seriously injured anyone?
  • Have you ever been arrested?
  • Would you ever watch taboo pornography?
  • If you wanted to kill me, how would you do it?
  • Would you let me (fill in the blank with an explicit and weird request)?
  • Have you ever found a child attractive?
  • Do you think teen girls are hot?
  • Guess how old I am?
  • How much do you think I weigh?

Embarrassing First Date Questions

First dates and blind dates are awkward enough without adding unwanted tension from badly worded questions. If you want to make it to the second date, avoid these embarrassing questions and stick with safe topics.

  • Do you love me?
  • Do you think you can fall in love with me?
  • Does this make my butt look big?
  • Am I fat/ugly?
  • Do you have enough money to pay for the date?
  • How much money is in your bank account right now?
  • Why did you dump your last girlfriend?
  • How many people have you slept with?
  • Do you want to get married?
  • Do you want to have children?
  • What's the most embarrassing thing that's ever happened to you?
  • Do you have any STDs?

Awkward Questions to Ask Your Boyfriend

What's the fastest way to turn a boyfriend off? Asking him probing or embarrassing questions before your relationship is ready for it. Every relationship has a personal evolution that begins with the first date and may result in marriage and parenthood or breaking up two weeks later. This personal evolution goes through different stages for each couple based on their individual emotional baggage and chemistry.

Embarrassed man on bed with girlfriend
  • Am I a better kisser than your ex?
  • Why are you dating me?
  • Do you think about your ex while you're with me?
  • If you could change one thing about my body, what would it be?
  • How expensive of an engagement ring can you afford?
  • Am I more important than your mom?
  • Would you ditch all your friends to be with me?
  • Which one of my friends do you think is the hottest?

Weird Conversation Starter Questions That Work

Sometimes weird and potentially embarrassing questions can work as fun conversation starters. Although they sound slightly embarrassing coming out of your mouth, these questions can lighten the mood. Look for funky topics that don't make his delve deep into personal feelings or anecdotes.

  • If you held a world record, what would it likely be for?
  • If you could be any insect, what would you be?
  • What location in the world are you least likely to visit?
  • What's the one app you couldn't live without?
  • Could you survive without your cell phone?
  • If you could be inside any game, which would you pick?
  • In an ideal world, how many hours a day would you be awake?
  • If you could go back to school for one year, which grade would you choose?

Embarrassing Questions

Many of these questions are curiosities that may or may not come up during natural conversation. When in doubt about a question, think about how you would feel if someone asked you the same thing. If your face begins to flame and you get that jittery, butterfly feeling in your stomach - don't ask it.

47 Embarrassing Questions to Ask a Guy