17 Personal Questions to Ask a Guy to Get the Inside Scoop


Men are mysterious creatures. Since they don’t divulge much, to find out what you want to know, you have to ask guys the right personal questions.

There are plenty of differences between men and women, but one of the biggest is how we communicate. Women are all about snuggling in with friends and talking, talking, talking. Men are more about snuggling in with beer, a koozie, and not saying anything. So if you’re going to ask a guy personal questions, you had better make them count.

Women are inquisitive creatures, and as hard as we sometimes try to let things “roll,” sometimes we just can’t. If you’re perplexed by his maleness, what he does on his own time, or how he feels, he is likely not going to open up when you ask him questions that may be embarrassing or too deep. The key is to keep it light, somewhat funny, and definitely non-threatening.

These are the 17 best questions to figure out what’s going on inside his head

The best way to know what makes a guy tick is to just ask. These are some personal questions that will get you the answers you want without offending, having him clam up, or embarrassing him.

#1 Why do guys masturbate? One of the biggest conundrums to women is why men spend so much time pleasuring themselves, especially when in a relationship. He may not even know the answer to this himself, but it is a question worth asking. [Read: Going solo: The 15 sexy benefits of masturbation]

#2 Why do guys pee outside? Now, you probably think this might only happen when they are camping or when no bathroom is available. But the truth is that a guy will pee outside even when he is two feet from the door. Is this something like marking their territory? Ask him to find out!

#3 What does it feel like when you fondle their balls? Lots of guys say that they wish their ladies wouldn’t neglect the balls when performing oral sex or even engaged in intercourse. We may have a pretty good idea about what sex feels like while stroking the penis, but what is the sensation when it comes to the testicular region? [Read: Blue balls facts every girl’s gotta know!]

#4 Why do guys pat each other on the butt during sports? Some guys barely like to hold a girl’s hand, but they have no problem running around patting each other on the backside. If a man can explain this to you, we’d all like you to share it with the rest of us.

#5 What do you really think about during sex? What is it that guys are thinking about when having sex? If it isn’t good, do they tell us? If they aren’t into us, do they just envision another woman? Do they think about their hot coworker? Likely, you won’t get the truth, the whole truth, and nothing but the truth, but it’s worth a try.

#6 Have you ever felt bad about a one night stand? You know how the walk of shame can feel to you, but have you ever wondered if the guy you were with felt any guilt when he had a one night stand? Men are different when it comes to sex—there is no shame for them. Do they think less of us, feel badly for using us, or do they just put it behind them like another notch in their bedpost? [Read: The 10 most common one night stand mistakes]

#7 Would you ever sleep with a hooker? Girls like to believe that the only man who would sleep with a prostitute is either one who is creepy and ugly, or who is a “has been” like Charlie Sheen. The whole idea of being with someone who would charge to have sex with you sounds awful to a girl. How does it make a guy feel?

#8 At what age did you have your first sexual experience? Most girls would be shocked to find out when their boyfriends lost their virginity. If you want to know a little about how he grew up, whether he was on the fast track or a late bloomer, this question will likely not yield the answer you expect… or maybe it will.

#9 What feels better: sexual intercourse or oral sex? The answer to this question will probably differ from guy to guy, but not all girls are willing to give oral at will. If a man could choose to have sex with you or to have you go down on him, do you know which he would likely pick? [Read: How to master the art of the perfect blowjob]

#10 If you could have sex with multiple girls at the same time while married, would you? Is he having a serious relationship because he wants to, or because there are benefits that outweigh playing the field? There is a difference between choosing happily-ever-after and knowing that you will have to settle down at some point, so you may as well do it now.

#11 Is the phrase “happy wife, happy life” true to you? Many guys insist that they are only happy when they can make the woman in their life happy. Are they altruistic in their need to make the one they love fulfilled in life, or is it for some self-servicing purpose? [Read: The 25 sweetest romantic gestures for everyday life]

#12 Do guys want a good girl or a freak in the sheets? It’s likely that every guy wants a girl who is a freak in the sheets, but only for him. Are guys attracted to bad girls, or do they just want their good girls to act bad for them?

#13 How often do you think about sex? Some statistics say that men think about sex as many as 20 times a day. Does it happen in response to something visual that reminds them of lady parts, a hot girl, or is it just a general thing that comes to mind?

#14 Why do guys like anal sex? Anal sex is a mystery to women. We have a hole that is supposed to be used for enjoyment, so why would you want to try one that is used for something else and designed as a one-way street? What is the allure of anal sex for men? Not every guy is into it, but statistics show that more often than not, if given the option, they would go for it. [Read: Why do guys like anal sex and should I give it a try?]

#15 Why do men like to watch lesbians having sex? It’s confusing to women why men want to be a spectator to something they are not invited to. You would think the fact that women are choosing to substitute men for toys, other sexual experiences, and another woman would be a turn off, but it isn’t. It would be nice to know what it is about lesbians that makes the male gender so hot.

#16 Why do guys sleep with unattractive girls? Is sex that awesome that guys are okay with sleeping with girls whom they don’t find attractive? Is it something that guys do to gain experience? Do they dream that the girls are other women?

#17 Do guys like strong women? Women who are strong and confident in the workplace have a harder time being seen as feminine and finding a mate. Men seem to be intimidated by a female who is independent, knows what she wants, can take care of herself, and is very strong. It would be interesting to know what it is about a strong woman that can be such a turn-off to a guy. Maybe your guy can explain it to you. [Read: What men want in a woman to be drawn to her]

If you have ever wanted to know the answers to some of these questions, what do you have to lose by asking? Just keep in mind that if you’re going to ask your guy personal questions, make them worthwhile.

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Julie Keating
Julie Keating

A writer isn’t born, but created out of experiences. No lack of subject matter, my life reads more like fiction than anything that could have been imagined...

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