28 Awkward Questions To Ask a Guy & A Few Embarrassing Ones Not To

Want to get to know a guy really well and embarrass him just a bit? Here are the best awkward questions to ask a guy and a few that are better left unasked!

Women are, admittedly, quite the inquisitive bunch. We always want to know things, especially if it’s about the guy we’re dating. And sometimes, using the right kind of awkward questions to ask a guy can reveal a lot more about him, because it puts him in a spot and he wouldn’t know what to say!

Sure, we don’t want to ask a guy embarrassing questions, but sometimes it is just needed.

Whether we snoop, spy, or simply outright ask, there are always ways to know what you really want to know! He may blush, he may laugh, but all said and done, you will have the answers that will reveal a lot about him!

[Read: 20 good questions to ask a guy and find out who he is]

Why ask these awkward questions?

What makes a question awkward? One of two things, you find it inappropriate to ask him, or he may have a difficult time answering it because he’d have an inappropriate answer.

But truth be told, awkward questions are something all of us have on our minds. You may not ask something, but you are thinking it!

And if you’re thinking it, and it’s something you’re itching to ask, why not just give it a go? It’ll be funny, and what’s the worst that could happen? He asks you the same questions back in return!

So if you do want to use any of these awkward questions to ask a guy, keep your own answers ready because he WILL ask you something similar as well. But the best part of all this, the big secrets and awkward questions will be out of the way, and you both can have a laugh at the same time as well!

[Read: 15 weird and silly questions guys wish they could ask girls]

The best awkward questions to ask a guy and get to know him

We all want to know things about the guy we like, especially if we want to date him. But, sometimes, the questions to ask a guy are embarrassing. They can be embarrassing for him or us.

It can be awkward to ask a guy something personal or sexual, but when you need the answer, you need the answer. Sometimes you just have to ask a guy those awkward and embarrassing questions.

Although it can feel silly at the moment, there is an art and necessity to asking awkward questions. You need to be sensitive with your queries and nonjudgmental when it comes to the answers.

The answers could give you so much insight into him, your future, and even how comfortable you are with him. Give this list of awkward questions a try, and work your way down the list.

1. What are you most scared of?

If you are dating someone, this is an essential yet awkward question to ask a guy. Whether his answer is the dark or losing you, it is good to know where his head is for the sake of your future together or separately.

2. What makes you feel insecure?

This might seem like something that is none of your business. You surely don’t want to share your insecurities with him, but you know how important it is.

By sharing this information, you know exactly what topics to keep positive or to avoid. If he is insecure about his abilities sexually, jealousy, his work, or he just feels weird about his hairline, knowing this can help him gain confidence. [Read: 13 signs of insecurity in a man that can ruin a perfect relationship]

3. Have you ever cheated on someone?

This is totally something you deserve to know the answer to when you are seeing a guy. Sure, he might lie, but it is a good sign if he is honest and explains his situation and what he learned from it.

The phrase, ‘once a cheater, always a cheater,’ holds some water, so you deserve to know what you’re dealing with.

4. What have you learned from your past relationships?

This is always an awkward question for a guy if it is about an ex, but it is also vital. You want to make sure he is over his ex. You also want to make sure he has learned from past relationships. If he goes on and on about how crazy his ex was, odds are he blames her for things he did wrong and will do the same to you.

5. Have you been tested for STIs?

If you are planning on having sex, you have to talk about it. It isn’t about trust or intrusiveness but about protecting yourself.

In the same way, you need to discuss birth control and not just assume the other person has it taken care of. This is a vital topic to talk about with a guy, no matter how awkward or embarrassing. [Read: How to have safe sex in every way it is possible to]

6. What are you sexual fantasies?

Sex isn’t all about touching and kissing. When it comes to sex, the golden rule is that you shouldn’t be having it if you can’t talk about it. That goes for safe sex and sexual desires.

It can be weird to share something that feels so intimate and personal, but you want to please each other when dating a guy. Offering up this vulnerable topic can bring you a lot closer and make your sex off the charts amazing. [Read: The top 50 kinky sex ideas worth trying at least once in your lifetime]

7. How experienced are you?

You don’t need to ask how many partners he has had because it is over the line. But an embarrassing question you can ask a guy is how far he has gone.

Whether he is a virgin, has been pretty wild, or what have you is crucial. You want to know what he is comfortable with and share your comfort level.

8. Do you regret anything?

Whether he lives with regret or regrets something minor, it is essential either way. It is awkward to ask a guy a question like this because he probably doesn’t want to admit to a mistake, but you know you have a keeper if he can. When a guy can own up to his shit, he is not full of ego.

9. What do you want between us?

Don’t be embarrassed and ask a guy about getting married, but you can and should ask what he wants, no matter how awkward. The ‘what are we?’ talk is always uncomfortable, but it is necessary to clarify your situation. [Read: How to get an answer to the ‘what are we?’ question]

10. What makes you feel the most awkward?

Is he awkward in social situations? Does he hate interviews or first dates? What makes him feel uncomfortable? Asking this can help him open up to you.

Just be prepared to answer yourself. Maybe you can help each other break down those walls.

11. What is the first thing you noticed about me?

This is always an awkward question to ask a guy because his answer could come out of left field. But, if you want to know what he first saw when he looked at you, ask. It could be very eye-opening. Was it love at first sight? Did he see a stain on your shirt? Or was he entranced by your beauty?

12. What is your most embarrassing moment?

This is a great first-date question to ask a guy. Yes, it is embarrassing, but that is the whole point. Showing that you and he can be humble and honest is a great way to know each other better.

13. When was the last time you cried and why?

Society has imprinted the idea into men that boys don’t cry. Of course, that’s rubbish! But what does he have to say about it? Did he cry while watching a movie? Or was it when something bad happened in his life?

14. What are your biggest goals in life, personal and professional?

This awkward question to ask a guy can help you take a peek into his dreams and desires. Does he want to be a millionare? Is he working towards it? Is he looking for true love? Is he content with his life? And most importantly, is he grateful for what he has already?

15. What is something you want to know but are embarrased to ask me?

Find out what he wants to know about you. Let him be the awkward and embarrassing one for a change.

[Read: 20 revealing questions to get to know someone better]

Awkward questions not to ask a guy

The problem with asking a guy embarrassing questions is that they aren’t always embarrassing for him. You could be embarrassing yourself with these questions. Not only are some questions awkward, but they show your insecurity, lack of trust and are way over the privacy line.

Of course, you can go right ahead and ask the guy you’re dating any embarrassing question you’d like. But then again, some awkward questions to ask a guy are better left unanswered. Due to our insistence on knowing anything and everything, we may sometimes turn a guy off.

If you’re the type of woman who refuses to give up without getting an answer from your guy, then this trait of yours can easily irk him. That’s why we’ve compiled a list of awkward questions that some women love to ask but really aren’t any of your business.

1. How big is it?

You know what we’re talking about. If you don’t know how big it is, then we assume you haven’t seen it. So why would you ask a guy how big his package is if you’re not even intimate yet? Is this some sort of qualifying question? If he answers with anything less than seven inches, would you dump him? What if he asked you your bra size?

Really, don’t ask. Just find out when you’re at that stage in your relationship. This is a super embarrassing question to ask a guy for a lot of reasons.[Read: How to know if a guy has a big dick – 18 clues to instantly know from afar!]

2. How many women have you slept with?

When it comes to awkward questions to ask a guy, this might just be #1. The problem with this question is that you may not always get an honest answer. Plus, it really isn’t any of your business. Would it be cool if he asked you this? Would you want to be judged for this?

A guy may give you a number based on two things. One, he doesn’t want to give too big a number for fear that you’ll think he’s some sort of womanizer. And two, he wouldn’t want to give too small a number for fear that you’ll start to wonder why he wasn’t able to sleep with more women.

3. Do you always have women over at your place?

Not only does this sound accusing, but again, it’s hard for him to be honest with this question. If you ask a guy this question, he’ll start to wonder why you asked.

Is it because his place is so testosterone-filled? Is it because it looks like the kind of pad a womanizing bachelor would keep? Even if you’re just asking it innocently, it might already trigger alarm bells in your guy’s mind. [Read: 24 sexy bedroom ideas that’ll arouse a girl when she comes over]

4. What are you thinking?

This is a pet peeve among many guys, especially when it’s asked right after sex. What do you want him to say? He just had sex with you, sure, but his mind is bound to wander away to other non-you-related things. This isn’t just an awkward question to ask a guy, but it is also pointless.

He might have to make something up off the bat so that you won’t get disappointed when he says anything less than how much he loves you or how good that session was! [Read: 10 things girls should never say to guys ever!]

5. Anything about his masturbatory habits

Let’s face it, guys jack off. Even if they have a girlfriend, they may, sometimes or a lot of the time, feel the need to adjust the antenna for their own satisfaction. With that said, they’re not always too proud of this for fear that you might think your sexual prowess isn’t enough.

This isn’t any of your business anyway. Asking about it is just going to make him uncomfortable! [Read: 15 things you do that turn him off while having sex]

6. Have you ever been attracted to another guy?

It’s okay if your guy is attracted to the male form. Have you ever been attracted to a woman? Whether it was sexual or not, it isn’t something he needs to know about you, and you, him. This wouldn’t make him any less decent or masculine.

But the thing is, if he wanted to talk about it, it should be of his own volition and not because you asked. This is more than an awkward question to ask a guy, but an inappropriate one to boot.

7. Do you think [name of your female friend] is hot?

If you think your friend is hot, chances are, he would think she’s attractive as well. When you ask this, you’re just putting him on the spot, and you’re not going to like the answer, whatever he says.

On the one hand, he wouldn’t want to make it seem like he has the hots for one of your friends. On the other hand, he wouldn’t want to say no for fear that it might come off as insulting to your friend. There’s really no winning with this question. This is a test and a mean one at that.

8. Which of your friends do you like the least?

Now you’re just asking him to tell you which of his friends he doesn’t like. Just making him think about it would make him feel like he’s about to betray a guy friend simply to satisfy your curiosity.

If you’re insisting on finding out which one of his guy friends he’s not that close to, say, “Which one of your friends do you hang out with the least?” That should take the edge off asking a guy this awkward question. [Read: How to get your boyfriend’s friends to like you]

9. What are your exes like?

For guys, when something is over, it’s over. It won’t merit another thought unless absolutely necessary. When you ask this question, you’re making the little clerk in his brain go to a dusty old cabinet in the back of his mind, pick out the files for his exes, and divulge whatever he can retrieve.

You may just be looking to find out if any of them are potential threats, but he’ll probably tell you in his own time. Just be patient. Plus, you should be more concerned with his experiences and what he has taken from them than what his ex is like.

10. How much money do you make?

You may probably already be able to deduce if he’s well off based on where he lives, how he carries himself, and what kind of job he has. But do you still need a specific number? Ask a guy about his finances when you’re engaged or living together, not now.

11. When do you think we’ll get married?

If you ever want a guy to run the other way, this is the question that’s going to do it. A seemingly innocent question like this not only puts him on the spot, it’s practically forcing him to promise when he’ll walk down the aisle with you. He may not even be entirely sure it’s you he wants to see walking down the aisle yet.

The only time this is an acceptable question to ask a guy is if you’re engaged or living together. It is an embarrassing and awkward question to ask a guy in the first six months to a year of dating. [Read: 16 ways to read your man’s mind and get him to propose]

12. What do you want to change about me?

Are you just begging your guy to start criticizing you? If he says that he doesn’t want to change anything, it may not be completely true.

However, whatever he wants to change about you, he probably won’t say what it is if you ask for fear that it will hurt you. He’s more likely to find a subtle way of helping you change that habit that drives him mad, and it’s not by telling you outright. [Read: 12 bad girl traits every guy wants to see in his girl!]

13. Me or [hobby]?

Whether your guy’s hobby is sports, online gaming, cars, or comic books, it won’t be fair to him to make him choose. This is an ultimatum even if you don’t feel that way, and it isn’t right or fair. How would you feel if he asked you ‘him or makeup’?

We know you’d only ask this if you feel that his hobby is why you’re not having enough quality time. But making him choose just like that will lead to him justifying how much he loves his hobby and you berating him for choosing his hobby over you. It’s a lose-lose situation that can only end in an argument.

[Read: 20 secret things guys really wish girls knew about guys!]

It’s fun to ask each other a few funny awkward questions and have a laugh about it. But don’t go asking something that’ll just leave one or both of you annoyed and upset. There’s always a thin line you need to remember, and once you cross that, it’s hard coming back from there.

There are tons of awkward and embarrassing questions to ask a guy. Some of those are important, while you should forget the others for good.