20 Awkward Questions To Ask A Guy

By on August 30, 2013

1. Who is your least favorite friend? 

Why it’s awkward: Asking a guy to almost directly bash one of their best buddies isn’t a comfortable situation.

2. What are your exes like?

Why it’s awkward: No dude wants to talk about his exes, especially in detail about their personalities.

3. Which of my friends do you think is hot?

Why it’s awkward: He’s probably feeling pretty anxious when you ask this question. Why?  Because he doesn’t want to risk making you jealous or hurting your feelings by saying he finds someone else, especially one of your friends, attractive.

4. How much do you weigh?

Why it’s awkward: Contrary to popular belief, it’s not only girls who sometimes feel self-conscious about their weight. Guys can also feel awkward when asked to reveal their weight.

5. What one thing do you wish you could change about me?

Why it’s awkward: If he answers and says ‘nothing’ then he knows you will think he’s lying. Now, he’s frantically trying to thing of an answer that won’t upset you. Do you really think a dude wants to tell you that there is something he doesn’t like about you? Nope, he really doesn’t.

6. When did you last wet the bed?

Why it’s awkward: No one, and I mean both guys and girls, wants to admit they ever wet the bed. It’s especially tough for a guy because, usually, they are more prideful than girls and it’s harder for them to admit to anything embarrassing at all.

7. Why don’t you work out?

Why it’s awkward: Are you implying that it looks like he’s never been to a gym in the first place? Or if he does workout and you ask then you’re pretty much telling him he looks gross whether he works out or not.

8. Which girls do you know that are prettier than me?

Why it’s awkward: Once again we’re back to the whole thing about how he doesn’t want to admit anyone is prettier than you at all. Even if he does find other girls cuter (which may or may not be true) he’s not going to want to tell you.

9. Have you ever regretted a past relationship?

Why it’s awkward: Guys are not ones to talk about their past relationships. Unlike girls, most guys don’t want to talk badly about their exes, let alone talk about their exes at all. Period.

10. Have you ever cheated on someone?

Why it’s awkward: Their now thinking one or both of two things: 1.) Do I seem like the cheating type? 2.) I have… but I don’t want to tell you because it may ruin your view of me.

11. What do I do that annoys you?

Why it’s awkward: There is usually always some irritating quirk we don’t like that someone does, even if we love them with all our hearts. No one’s perfect, but does he really want to tell you that you aren’t perfect? That’s definitely an awkward situation right there.

12. Where do you see yourself in 5 years from now?

Why it’s awkward: They’ll not know how to answer this question. Well, most guys, anyways.Guys are more of the type that thinks in the now and rarely about the later.

13. Can I meet your parents, like, soon?

Why it’s awkward: It may not seem all that awkward, but if you are the one to ask first then the guy you’re asking may feel overwhelmed and awkward. He may not be ready for you to meet them, whether you’re a friend or a girlfriend.

14. What was your exact thought the moment you met me?

Why it’s awkward: Remember how we discussed that guys think in the now and not the later. Yeah, they don’t think about the then either. They probably didn’t hold onto that thought, so what are they supposed to tell you?

15. Have you ever tried peeing while sitting down? 

Why it’s awkward: Either they have and that’s embarrassing to admit or they haven’t and it’s weird that you even asked. Oh, the masculinity.

16. Are you a virgin? 

Why it’s awkward: Do you think he’s a virgin? If he isn’t, he’s probably wondering why you would think that he is one? And if he is a virgin,  he’s definitely going to feel awkward about truthfully answering that question.

17. How much money do you have/make?

Why it’s awkward: Finances are awkward to talk about. If he has no money, he may be embarrassed to tell you and if he has a lot, he may think you want to use him for his money.

18. Would you marry me someday?

Why it’s awkward: If it’s earlier in your relationship, he’s going to feel awkward about answering this. He may want to and then feel weird about telling you so. He may not want to even think about it right now. Or he may not actually ever see himself marrying you and he doesn’t want to let you know that.

19. Do you like our current President/Congressman/Governor/Etc?

Why it’s awkward: Watch out for any political questions. Especially if you haven’t known each other long or have known each other for awhile, but haven’t discussed this kind of stuff. He’s going to feel awkward about answering this because what if you like the mayor and he doesn’t? If he answers that he doesn’t then he knows he may risk upsetting you. He doesn’t want to drive a wedge  between the two of you because of political beliefs.

20.  Why do you do that?

Why it’s awkward: Pointing out something that he does that is weird is awkward. Asking him why he does it is even more uncomfortable because it’s just a habit he has and he doesn’t know how to explain why he does it. Now, he knows it bothers you and it’s going to be awkward every time he does it.


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