Embarrassing Questions To Ask A Guy

When in a romantic relationship, there are many embarrassing questions to ask a guy that might arise. If you’re concerned about annoying or abashing your boyfriend, you might want to avoid these questions.

They could cause an awkward situation for both of you. Just because a question seems harmless to you, doesn’t mean he’ll see things the same way.

Remember that men are sensitive creatures, despite their masculine bravado. Although they may seem aloof, they are most likely just masking their real feelings with indifference.

Some of these questions might hurt his feelings or at the very least, make him squirm under your scrutiny. They may cause discomfort, tension or send him running for the hills. However, if you’re willing to take that chance, ask away! Here are the top ten most embarrassing questions to ask a guy.

Note: You can also see our original post Questions To Ask Your Boyfriend

Embarrassing questions to ask a guy

Do you love me?
How many other girlfriends/partners have you had?
Do you want to get married?
Do you want children?
Do you think I’m fat/ugly?
What don’t you like about me?
Are you a virgin?
What’s your IQ?
What is your best-kept intimate secret?
Am I better than your last girlfriend/partner?

These questions are most embarrassing when the relationship is still new. If your boyfriend has never told you he loves you and you ask out of the blue, that can lead to a very uncomfortable situation. Plus, he might not answer the way you’d like. Asking how many partners he’s had before you can also cause embarrassment, particularly if he hasn’t had that many.

Asking questions about the future, marriage, and children is also off limits for new relationships, unless you’re trying to create an awkward silence. This could make things seem too serious and make him feel like the relationship is moving too quickly. Avoid these embarrassing questions until you know each other better.

The classic question, “Do I look fat?” can also make a man’s cheeks redden. If you haven’t been dating long, he’ll feel obligated to tell you no, even if it isn’t true. This can make him very uncomfortable and you might not like the reaction you get. It will also make you seem insecure and this isn’t something most guys are looking for in a girlfriend.

Virginity is another topic that can be very personal. Perhaps your boyfriend is saving himself for someone special, or maybe he’s been around the block. Either way, asking him about it before he chooses to confide in you himself can cause problems. He may feel pressured to answer untruthfully, especially if you’re in mixed company.

Intelligence can also be a touchy subject for many men. He may feel like you’re trying to assert your superiority if you ask him about his IQ, grades, etc. This can lead to feelings of inferiority and resentment. It’s best to let him talk to you about this only if he chooses. Plus, you can probably figure out how smart he is from a few minutes of conversation anyway.

Asking about previous relationships is also a no-no if you want to avoid embarrassment. It’s possible that he might not be completely over his last flame. This could be awkward for both of you.

If you want to stay out of these mortifying situations, avoid these embarrassing questions. Some shouldn’t be asked at all and others breached very carefully. When the relationship is fresh, any one of these questions could ruin the fun in an instant.

For more questions to ask a guy, feel free to download your copy of the free 100 Questions Before Marriage sample eBook or 1000 Questions For Couples today!


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7 Responses to “Embarrassing Questions To Ask A Guy”

  1. reena Says:


  2. bianca Says:

    My husband thinks I’m silly asking him silly questions ,but they help ,so thankx

  3. bianca Says:

    Its kool

  4. Michael Says:

    Personally I don’t see why these questions are considered embarrassing. I do appreciate your explanation of why you believe they might be for some people. I think the What don’t you like about me? to be the most uncomfortable question to answer but embarrassing…?

  5. brakk Says:

    girls never ever ask a guy any of these

  6. Cheryl Says:

    These questions arent embarrassing -_-

  7. IeatCcomputersandtheytastesupergood Says:

    LOL i asked one of these xD

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