20 Awkward Questions To Ask A Guy

Awkward Questions To Ask A Guy


20 Awkward Questions To Ask A Guy

We have all had that moment where we have said something without fully thinking about it first. You know, that foot in the mouth type of thing.  It sounded so good in your head but as soon as it comes out you realize you just want to crawl into a hole and hide.  A lot of times this happens when us girls try to talk to a member of the opposite sex.  Guys are strange creatures; the men are from mars and women from Venus kinda strange.  So something that seems totally fine and normal to us emotional and vocal females may come across as a bit… well, awkward to a guy.  I’ve asked around and found out some of the most uncomfortable, awkward and sometimed interesting questions that guys have been asked and why we should avoid asking them.  I hate to say it, but after hearing these answers I’ve probably have asked a third of these questions and embarrassed myself.  So do yourself a favor and find out what NOT to ask a guy and avoid the awkward conversations.

1“How much do you make?”

Ok, this one I absolutely would never do. I keep my finances (the little money I have) to myself. When you’re dating around and you’re trying to know more about a guy and his career just simply ask what he does for a living and leave it at that. If you’re that desperate to know what he makes there are always sites that will give you a ballpark estimate of different careers in various cities that will hopefully give you an idea.

2“How much money do you have in savings?”

Just like asking how much money he makes, asking how much money he has in savings is really none of your concern.  If things are serious and talks of having joint bank accounts are brought on the table then it is much more understandable to ask but otherwise just avoid it.

3“How much debt do you have?”

This question is awkward and will be a very uncomfortable topic of conversation and should be avoided if you are casually dating but, if things are getting serious and you could possibly see yourself with him in the future you should know what you’re getting yourself into. To be fair, if you’re asking him about his debt make sure you come clean about yours.

4“When’s the last time you talked to your ex?”

I have been very guilty of this one…it’s a legit question! If I’m dating you, married to you, whatever we are to each other, I want to know when the last time you talked to your ex was.  In the beginning of a relationship it’s a bit more understanding since you are learning about him and well, who he hangs out with. After you’ve been with the person for a while if you’re asking it shows that there is lack of trust and maybe it’s your gut telling you something.

5“Are you still in love with your ex?”

This is a very uncomfortable question since you may think you know about his past relationship but the only people that know the truth is him and his ex.  It’s okay for him to still have love towards her since they obviously had something at one point but don’t take it personally.  If you trust your guy you shouldn’t worry about his past or his exes, he chose you; remember that.

6“Was your ex better than me?”

First off, are you prepared for this answer? Do you really want him to be truthful with you or are you looking for him to compliment on how amazing you are? If you want the truth, can you handle the truth? Will you get upset and use it against him? Rather than needing to hear the answer to the question, think to yourself is knowing this information going to help me or make things better or am I going to be crying as I stuff my face in icecream. You can decide that one.

7“Do you think your ex was prettier than me?”

Just like asking if their ex was better than you, asking if she was prettier than you can only lead to no good.  You are beautiful, you know that but even if you feel like she was prettier and you just want to hear it from him, do you REALLY want to hear the truth?  He’s not an idiot; no matter if she was smoking hot and put you to shame he will NEVER tell you that she was prettier. Even if she was, he’s interested in you and all your amazingness. She has nothing on you!

8“Who is the girl that liked your photo?”

Well, thanks to social media it has brought stalking exes and ‘competition’ to a new level.  This was a question several guys admitted was awkward and they couldn’t stand answering. Girls, they are allowed to have friends and you know you have had guys ‘like’ your photos. It’s a friendly gesture. Don’t bother asking and making it something it’s not.

9“Can we have a joint page?”

Almost everyone has a few profiles on their friends’ list of couples who have a joint page.  Majority of the time it’s the female half asking for this so they can keep a watchful eye on their guy.  Trust your guy and let him have his space with his friends.  I personally wouldn’t want my husband reading my emails between my friends, not that they are inappropriate but they are simply none of his concern.

10“When can I meet your parents?”

I know the intentions are innocent enough with this question especially when you want to know about his life and who raised him etc…but, what if he isn’t ready for that commitment yet?  Let a guy do this on his terms. You don’t want to make him take a huge step like that when he’s not ready.  It doesn’t mean he’s ashamed of you, it just means he wants to make sure it’s the appropriate time.

11“How many sexual partners have you had?”

Ugh, I hate this question.  I have had guys answer with only a couple to ones that admitted to practically sleeping with the entire girls’ dorm! If you’re about ready to have sex with your guy you have the right to know for your safety but if you just started seeing each other, avoid asking it right away. Not only will it make things uncomfortable quickly but what if he’s an amazing guy but has a larger number…he doesn’t want to ruin his chance with you. Ask once you’re ready to take things further.

12“How long do you usually last during sex?”

OMG! I couldn’t believe a few guys I asked had said they’ve been asked this at one point or another. Ladies, who cares how long they last as long as they know what they’re doing. Don’t embarrass them with such a question and it makes you look like that’s all you care about…not okay, ever.

13“So, how big are you?”

I totally understand that curiosity, I do but that’s a pretty personal question.  What if he’s insecure or isn’t even ready for sex yet and you put him on the spot like that…that may be the last time you hear from him.

14“Do you watch porn?”

This is such a personal question and many girls ask this in hopes a guy says no, or that they will stop for them.  What harm is it causing you with them watching it? And as several guys have answered, they will watch it without you knowing if they really want to. Pick your battles girls.

15“When will we get engaged?”

Whatever happened to the element of surprise?! Don’t put the pressure on him if he isn’t ready. Would you want him to feel rushed to propose and it end with cold feet or divorce or even him telling you that you’re not the one?  Let him decide whether or not he is ready for it and don’t rush into such a big commitment.

16“Why won’t you marry me?!”

Oh boy, so this is a pretty popular question.  I personally have never asked this since I met my husband at a young age but as little girls most of us plan our wedding even before we are in elementary school.  We may feel that we are ready for that next step but in reality, he may not be ready. It doesn’t mean that he hasn’t thought about it or doesn’t want to at one point or another, but don’t rush it. Let him genuinely want to spend the rest of his life with you, totally committed.

17“Do you think you could tattoo my name on you? Show me you really love me”

Ok, so I have been with my husband for almost fourteen years, since I was in high school and I would never, ever, everrrrr get his name tattooed on my body. Yes, I have tattoos and love them but it’s a terrible idea especially since relationships aren’t guaranteed to last forever.  If he wants to get your name on him that’s on him, but don’t make him show you he loves that way…settle for a cute love note or a romantic date.

18“Does this make me look fat?”

Oh yes, I have done this on numerous occasions and have had my husband say ‘you look great’ EVERY time.  It’s not that I actually looked that great, trust me, my best friends have spoken the hard truth with some of my outfit choices but it was him avoiding hurting my feelings or getting me mad.  Do you really want to hear him say that something you’re wearing makes you look fat? If you want a real opinion ask your best friends, that’s what they are there for.

19“Do your friends like me?”


You adore everything about him and he seems to feel the same way but do his friends?  You may be tempted to ask him if his friends like you but really, do you think he wants to put his friends on blast if he knows they don’t? Be yourself and know that he’s the only person that you need to impress and know how important his friends are to him.  So what if they don’t like you, you know you’re awesome and that’s all that’s important.

20“Why wasn’t I invited to guys’ night?”

You know the silly side of you when you’re with your friends? All that girl talk and things you couldn’t imagine talking about with anyone other than your best friends? Well, just like you, he has his own set of friends and needs to be able to be his self with the guys. It doesn’t mean there are strippers and clubs, majority of the time it’s video games, sweats and not having to have a ‘real’ conversation that he’s enjoying with his buddies. So let him have his time and go have yours!

Overall, all guys are different and what may make one want to run for the hills may not be a big deal for another.  Feel out your guy, get to know him and see what seems to make him uncomfortable and try to avoid putting him in that situation.  I know it may seem tough (ok, really tough!) to hold some things in when you’re dying on the inside to find out, but ask yourself not only can you handle the truth, but do you REALLY want to know.  Don’t overstep boundaries or else your relationship won’t be based on a solid, trusting structure.  Guys are totally different creatures and they really may not be thinking anything when you ask what’s on their minds so do yourself a favor and spare yourself from those awkward questions.  Trust me, I’m saving you from yourself!



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