Embarrassing Questions to Ask a Guy

Heather Long
Don't ask an embarrassing question again!

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 in the first stages of a relationship can be embarrassing for both of you.

Don'ts: Embarrassing Questions to Ask a Guy

What's the fastest way to turn a guy 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.

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. The following are some examples of embarrassing questions to ask a guy:

  • Why did you dump your last girlfriend?
  • Am I a better kisser than she is?
  • Why are you dating me?
  • Do you love me?
  • Do you think you can fall in love with me?
  • Does this make my butt look big?
  • Am I ugly?
  • Do you think about your ex while you're with me?

Pushing the Envelope

Most questions that embarrass 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.

Some Examples:

  • How many other girlfriends have you had?

Your partner may not want to answer this question for any number of reasons. He may not have kept count. He may be embarrassed by the high or low number himself. He may not think it's any of your business.

  • Do you want to get married?

Questions like this suggest you want to get married. This is not a question you ask on a first, second or even third date. This discussion comes up when the relationship has evolved and is ready for the next stage.

  • Do you want children?

The children question is another no-no for early relationships. Children are a serious commitment and should be the product of a long-term relationship, not the reason for one. It's a difficult question that can lead to an even more embarrassing discussion.

  • Do you think I'm fat/ugly?

What is a man supposed to say to that? Is he supposed to say yes, thereby hurting your feelings and creating tension or is he supposed to say no and try to help you overcome your own feelings of insecurity. This question leaves no winners behind no matter what the answer is.

Embarrassing Questions

Asking your boyfriend questions about his sexuality, sexual experiences, or sexual history beyond the reasonable discussion of birth control and venereal disease prevention can open a can of worms for both of you. The most embarrassing questions you can ask a guy are those that broadcast your insecurities.


Many of these questions are curiosities that may or may not come up during the course of natural conversation. Some are inappropriate unless your boyfriend volunteers to share. Some are just plain embarrassing for you as much as for him. 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.

Embarrassing Questions to Ask a Guy