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Questions Not To Ask A Guy (49 Questions to Avoid)

by Sonya Schwartz

Communication certainly makes friendships and relationships go round, if you are trying to build one or the other, prodding for answers is inevitable. However, there are some questions you should never ask a guy unless you are in a specific kind of relationship. 

That includes your boyfriend, especially in the earlier days of dating, your guy friends, perhaps even your husband in some cases. A single list could never contain all the things that are better left unasked, but this one makes a point of being as inclusive as possible. 

Any question that pops up here is either one you don’t really want an answer to, too sensitive to just move on from after answering, or both. There’s also the case of asking too early or using the wrong tone of voice. That said, the following are some things you shouldn’t let sheer curiosity push you into asking a guy.

Contents

49 Questions You Should Never Ask a Guy

1. Bet you do this with all the girls /do you do this with every girl?

Some girls are as notorious with this statement as some guys are with the “do you come here often” question on every queue. First of all, if he says you are pretty or pays you any other type of compliment, just take it. Why make things uncomfortable for everyone by asking if he says that to every girl? What if he does? What if he doesn’t?

In a best-case scenario, he has played the script out long enough to give some basic witty comeback. Worst case? He’s as tired as the routine itself and just assumes right away that you are not worthy of his attention. Either way, there’s no good enough reason to revert to the old ways like this.

2. Am I hotter than XYZ?

If you must know if another woman has got it more than you, literally anyone else around you is a better fit to ask than the guy you are dating. You will either end up digging the conversation into uncomfortable depths, or he avoids the awkwardness altogether and says what he thinks you’d like to hear.

I don’t know about you, but anything slaps less if I get the sense it’s not coming from a sincere place. But what more can you expect from a question with no correct answer? PS: even if you are hotter than the said person, you still lose several points for being insecure enough to ask in the first place.

3. How big is it?

How big is it

I thought it was ironic putting this one so early on in the list, given that’s exactly when you shouldn’t be asking it. Why do you ask? A, you put the man in a difficult position if he isn’t, in fact, packing, one that might force him to lie to avoid embarrassment.

B, wanting to know a guy’s size might be driven by natural curiosity if you are attracted to him, but think about the damage A can do to your budding chemistry. There’s also the disappointment you are bound to experience down the line if he resorts to lying to save face. If you are that curious about his man meat, wait your turn to find out.

4. Does this dress make me look fat?

‘Em, no, it’s all in your head.’ ‘Uh, actually yes, all those workout sessions you’ve been missing are starting to show.’ ‘You look beautiful/perfect, baby, no matter what.’, etc. Any of these make you feel better? No? Exactly.

Just like it isn’t fooling anyone that what this question is really asking for is validation, there’s no right way to answer it either, especially when you ask the guy you’re dating. You might have better luck asking your male sibling or friend, but I’d generally stay clear of asking this particular fashion advice of someone I still hope to have sex with.

5. Every other weight-related question.

How much do you think I weigh? What’s your ideal weight in a girl? Would you still love me if you can no longer lift me, or whichever other Machiavellian way you can put it? If you are asking this question, my money as a girl is that you really can’t take the answer, no matter what he says.

Since it’s your own insecurity feeding the question, you will circle right back to the fact that you must be too over/underweight for his taste. So instead of playing that game, why not skip to the part where you actually do something about the source of your self-consciousness and save you both the fallout?

6. How old do you think I am?

A close second to the weight question is the age thing. It’s no news that most women find it inappropriate for a guy to ask their age, so men generally stay clear of that one. Understandably so, given what aging does to how a woman is perceived in society.

Now, knowing all that, wouldn’t you consider it a shit test of sorts if someone asked you that? Why put a guy through unnecessary palpitations by asking him something so sensitive? My advice? Don’t ask a guy to guess your age unless you are prepared to hear the wrong answers, which unfortunately might even mean your correct age.

7. How many girls have you been with?

Ah, the fabled body count question. Many girls make the mistake of thinking it’s just guys who aren’t supposed to ask this. While it’s not written in fine print anywhere who can ask whom about their previous sexual partners in a relationship, the rule is more about self-protectiveness than anything. 

You don’t need his entire sexual history to determine if he’s clean. They have STD tests for those. Besides the fact that the answer will only put you on edge, one way or the other, are you prepared for him to ask you the same thing? Because if you go there, he’d likely want to know yours too.

8. Am I your best yet?

While we are on the subject of sexual history, my gender has another angle to asking men, even if it doesn’t guarantee any better answers than the above. This question can come up in contexts outside of sex, of course, but given the [unofficial] statistics, it’s usually asked intimately in comparison to your predecessors, i.e., his exes.

The only truly satisfying way to get that information is if he expresses it without being probed. If you have to ask, it might still be true, but you’d never know for sure. Maybe settle for being the best you can be with him going forward instead of comparing yourself with ghosts of exes past?

9. What's your ex like?

Like the sexual history question above, the details of past relationships are personal too, and you shouldn’t make someone talk about it unless they want to. Naturally, if you are dating a guy, he should get around to telling you how his previous relationship went in due time.

You are also more likely to get the real this way than if you bring it up on the first or second date. Asking this to men too soon would only make him give you a censored version of events based on what he thinks you might be comfortable hearing, even that may not be easy for him.

10. Do you ever think about her (his ex) when we're together?

There will always be this battle with your love’s exes for as long as relationships exist, and showing how much you think about them weakens your position. Asking your man if his ex ever crosses his mind or if he has a love for her while he’s with you means you think about his ex while you are with your partner.

How would you feel knowing what’s going on in your guy’s mind while he’s with you is some guy you used to date? We all fight jealousy, but you are essentially arming the other side against you when you plant seeds like that in your boyfriend or husband’s mind. How? Because the question will most certainly cause him to think about her now if he wasn’t before you brought it up.

11. Does she do [anything] better than me?

Whether it's giving massages or head, whoever ‘she’ is (ex, mistress, colleague, or just a friend) just... don't. The same goes for asking if she's prettier/funnier/hotter than you, they both reek of jealousy and insecurity. 

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Let's you and me answer it together; if he says yes, on top of how hurtful that would be to hear, it'll make your insecurity worse. If he says no, it wouldn't be groundbreaking because it's kinda what he's supposed to say, so you won't really believe him. The way I see it, the only way to win at this game is just not to ask.

12. What's so special about your friends?

What's so special about your friends

Whether your guy moves in a pack or has most of his friends online, one thing you can count on with men is how important friendship is to them. All their buddies may not be the best of the bunch, they may not even see eye to eye on most days, but they usually have their reasons to keep them around.

Now I know how frustrating boys’ nights and the time he spends online/playing games can be, especially when it eats into your couple time. But it’s a small price to pay, I guess. Or not. If his friends bother you so much, face the problem head-on and talk to your man about recalibrating his attention meter. However, please don’t put him in a position to defend his friends while you are at it.

13. Should I change my hairstyle?

We all get those moods(?) where we think something drastic is the next box to check on our appearance checklist. Hair being one of the staples of beauty is often one of the principal sufferers. While there’s always room for spontaneity, most women won’t cut their hair without weighing the pros and cons about a few hundred times, at least.

Even if you have a hard time deciding what to do, never ask a guy you are involved with for a second opinion on such matters. On the off chance that he doesn’t see it as a trap, he might truly love your current ‘do or the one you’re proposing too much to be objective.

14. Should I get a boob job?

Likewise, it's especially meaningful to ask an ample boob guy, for example, if you should work on your girls. First of all, that decision is yours to make, never your boyfriend’s or your husband’s. That's as personal as things get. Two, you know the only thing this guy loves more than C cup breast size is you, A cup and all. 

Now putting him in a position to get a fantasy he probably doesn't even think about anymore or make you feel good about your body is unfair. If you want to get your body done, fine, but don't put it on your partner, especially if it tempts his sensibilities.

15. Do you ever whip it out?

Yeah, um, why? I get that we have strange curiosities, especially around organs that we do not have (case in point: girls to the penis, guys to boobs). But if you are going to ask a guy something that suggests he gives creep vibes, better do it prepared for the possible fallout.

The jury is still out on asking guys about their masturbatory habits. Asking if he goes around whipping his member out sometimes for no reason whatsoever might make him question how you see him.

16. Do you still work out?

The 'still' is intentional, believe me, he sees the dad bod, too, unless your superpower is spotting a beer belly before even the bearer. Guys may not show it as much, but they get self-conscious, too, maybe even more than girls sometimes.

Mind you, this is not the same as asking if he still goes to an old gym or something, this here is a sub, and you know it. You want your man to burn a few? Find better ways to tell him. 

17. Can we talk?

It's funny how we reserve the ‘we need to talk’ statements for serious conversations when they are, in fact, when we should avoid them the most. Never ask a guy if you can talk unless your primary goal is to make him panic and not just prepare him for the importance of said talk.

The more himself you want him to be in the discussion, the less good it will do you to open with such anxiety baits as those dreaded three words.

18. Can you get something right for once?

As you can probably already tell, the problem with this particular question is the tone. Likely to get roused by frustration or any of its relatives, expressing yourself that way may not get you your desired result.

Experts suggest removing statements like “never,” “for once,” and “always” from our communication linguae in a relationship, especially during arguments. Not only are they often exaggerated, constantly hearing how they never do something right can make your partner feel overly criticized and underappreciated. All feelings that may never pass, even after the fight ends.

19. Why aren't you more like that guy?

They say comparison is the death of joy, but if you want to find out how fatal it can be to love, too, ask your boyfriend why he isn’t more like someone else. Guys who score high on the self-love spectrum might even consider that a relationship deal-breaker because such a question suggests who they are isn’t enough for you.

No one is perfect, not even that guy who seems to have everything your man doesn’t. If there’s something you’d like to inculcate in your relationship or qualities you wish the man you love shared, you owe it to him at least to find a constructive way to communicate that.

20. Won't you introduce me to your family/friends?

It’s the natural progression as relationships go, to get to a point where a couple tries to bring their respective worlds together by meeting each other’s family and friends. For some, it’s as casual as any other day, while others tend to want to wait till things are a bit more steady before introducing a partner.

If you’ve only been dating a guy for a hot minute, and you haven’t talked about your relationship’s future yet, don’t put him on the spot like that. And if you are convinced you’ve reached that stage as a couple and it doesn’t seem forthcoming, then there’s a whole other conversation to be had with your s/o. 

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21. Why is your family so [something not positive]?

We all have details of our personal lives we usually prefer to keep out of our dating lives or other relationships, for that matter. Most people who wait till they are sure or in love enough to introduce their partner to their friends and family consider this question a major fear.

I know we don’t all come with a filter, and you may mean no harm by insinuating his loved ones are weird but think about how you’d take it if the roles were reversed. And even if you wouldn’t mind, it doesn’t mean another person who cares about that sort of thing won’t.

22. Would you still love me if...?

Would you still love me if...

If there was ever a time when hypotheticals worked for testing your partner’s love for you, it’s long gone. Now they are a cliché and, quite frankly, top of the list of questions you should never ask a guy if you want to be taken seriously.

Juvenile undertones aside, can you point to one girl or one time you asked such a question and convinced them they love you by their response? No? Go figure!

23. Me or yo mama?

I promise you the only person bothered about who's more important to your guy between you and his mom is you. It doesn't matter where she sits in the car or how much hold she still has over him, she'll never be you and vice versa. Think of it as a different kind of love in each case.

And newsflash, no matter what an average guy's answer to this question is, the fact that you even ask will make him look at you a little differently, at least. Like you shouldn't ever put your partner (or anyone) in that position.

24. Ever seen your mom/aunt/grandma/sister naked?

You can ask a guy this, but only if you absolutely hate him and want him to literally die of embarrassment. Ok, maybe I’m being a little dramatic, but, why would anyone even want to ask this, except perhaps during truth or dare?

The answer is probably yes for most guys, accidentally or otherwise. Still, if your guy is anything like most, it’s probably not something they go about sharing proudly because again, why?

25. Do you even like me?

Maybe you’ve been dating for a while, and it doesn’t seem like he’s feeling it as much as you. Or you caught your guy in a lie where his motivation for seeking out a relationship with you is more than just love and the usual stuff.

Perhaps you’d be justified to ask if he even has feelings for you if you caught him on top of someone else on your anniversary. But outside of those scenarios, I’d gladly file that under questions you should never ask a guy because again if I have to ask…

26. Do you (still) love me?

Or if he thinks he can fall in love with you. Also, “are you bored of/still attracted to me,” or like, “are you tired of being with me?” For starters, I know we all see how manipulative this can come off, so these are not easy questions for girls to ask on a normal day.

However, sometimes in love, your anxiety gets the best of you, especially when intimacy is no longer as tight as it used to be between you as a couple. As committed as your guy may be too calming your fears with reassuring answers, it might be more productive to address the underlying reason behind the probe than asking overly simplistic questions like these.

27. Can you give up social media for me?

Sure, many of us could use a break from social media and less screen time in general, but not even that is reason enough to ask your guy to give up this hobby. You might think it’s an act of love if SM is doing him more harm than good. To him, though, it would feel like you are asking him to renounce the community he’s built and likely his most extensive network.

If not a threat to him or your relationship, I suggest letting it lie, and if he’s addicted, for example, then stage an intervention or something because ultimatums will do you no good. 

28. How much do you make?

If you are ranking questions you should never ask a guy you’re dating by order of importance, this one should be somewhere on top. I mean, it’s only right to know these things if you are getting married and merging your finances, but on the second date? Without him asking you for a loan or something? Why do you need the number?

You can probably presume based on his lifestyle and other tells, but to ask outrightly when your relationship is clearly not there yet is to make an average guy apprehensive for no reason.

29. ATM pin, phone password, etc.

If you agreed it’s better to never ask your guy about his finances down to the number before your relationship is there, then this should be quite obvious too. Believe it or not, being in love or a relationship with someone doesn’t nullify your right to privacy.

Transparency is a recipe for relationship success, but some things mean more when done without asking, and this is simply one of them.

30. Would you ever let me go through your phone?

You might see it as a test of trust asking a guy this, but if he had something to hide, what do you think he’d say? If you guessed a blatant “no,” then you obviously haven’t crossed paths with a lot of pathological liars since you’ve been dating.

The real cheats like to hide in plain sight, so the last thing they want is to give answers that might put you on to them. The lying aside, though, wanting to snoop through your man’s privacy like that might indicate some personal and relationship issues worth addressing.  

31. Do I snore/talk in my sleep?

Sleeping conditions have been constituting a problem for even married couples probably forever. Snoring, for instance, is something nearly everyone does now and again, although there are those with chronic cases.

Even though they shouldn’t be, conversations about such sleeping conditions can be awkward, especially when the relationship is new. So, don’t be surprised if you ask your boyfriend and he gets tongue-tied or lies.

32. Which of my friends would you have sex with?

Even when you frame this within a hypothetical window where there are no wrong answers, guys know better than to fall for this. You can promise all you want, maybe even believe that you won’t be phased if he chose one, but you’d still get jealous.

Also, no matter how much you love and trust your girlfriends, leaving him with whomever he chooses in the same room henceforth will feel somehow. They call them questions you should never ask a guy, not just because they are taboo, but because once you know some things, you can’t unknow.

33. Which of my friends do you like/dislike the most?

Adding to your man's chances of cheating on you with your girlfriends isn’t the only reason to avoid these problematic probes. What good do you think could come of hanging your friends out like clothing for your man to pick at?

Just as you should ideally strive to present your relationship and partner respectively among your circle, your friends deserve the courtesy. Your man respecting your friendship is respecting you, so keep your girls’ business out of your love life as much as you can to avoid overfamiliarity.

34. You really believe that?

You really believe that

‘Do you really think that?’ ‘Are you sure about that.’ and similar stories. Whether he is talking about how much love/respect he has for you, or the potential he sees in you, or you are arguing, stop answering these questions. Questions that suggest your first reaction to whatever comes out of the guy's mouth are being doubted.

I get that they are probably meant to be rhetorical half the time, but it’s not cute to do them all the time, even if you don’t expect an answer.

35. Do you look at other girls?

Without sugarcoating things, this one sits tight under the category dumb questions to never ask a guy because [sigh]. Unless you take the term love is blind literally, being in a relationship doesn’t mean your eyes stop working, so of course, he looks at other girls.

Chances are you look at other guys too, doesn’t mean you want to date or sleep with them all. And even if you do and he shares your fears, the very fact that you are still with each other and not those other people should count for something, shouldn’t it?

36. What if I got pregnant?

People in a committed relationship can ask this whenever, but if you and your man have been dating for all of five minutes, I’d avoid this question altogether. At that early stage as a couple, your relationship is still very impressionable, as is your partner’s mind.

It is the stage of overthinking and reading meanings to regular statements, so imagine how explosive the pregnancy talk could be, especially when he is nowhere near ready or doesn’t want kids.

37. Why do you cry so much?

Many men still have a hard time accepting that crying and letting their feelings out generally is good for them. Those who do feel more like the exceptions than the norm and the last thing they want is for their significant other to ridicule them for it.

If you are dating a guy prone to tears, I’m sure there are more tactful ways to find out the underlying causes, if any, than making him feel like less of a man.

38. What are we?

I’m inclined to believe that the reason guys get up or fall asleep right after sex, besides biology, is to avoid the ‘what are we?’ talk. An average girl sure knows how to pick her time when she wants to get that kind of convo in - the moment when he’s most vulnerable and receptive.

This is not to say that you should never initiate the discussion, only to do it right, which hiding behind post-coital bliss or whatever, is not. Same energy as why are you dating me?

39. Are you (sure you aren't) gay?

If a guy you suspect might like guys is on your case, chances are he’s either trying to hide or is still figuring out his sexuality. Now, you know how sensitive that stuff is and should know better than to risk making him feel exposed by asking like you are accusing him.

If you must know, try to frame it like you’re genuinely interested and not in some awkward way that would automatically get him on the defensive.

40. What about me do you wish you could change?

This is one of those questions you should avoid asking a guy because it will open a can of worms. Good luck getting him to admit he thinks you are human and not Venus herself in the flesh. And even if he does, to what end?

You give people an inch, they historically take a mile. If you make it ok for him to single out parts of you to criticize, how long till the number increases and you start resenting him for being too blunt? 

41. Why are you so insecure/damaged?

There are ways to make a guy open up about his insecurities and similar issues without sounding judgy and condescending. In fact, a plain what are your insecurities or what was your childhood like would do better justice to the subject than a snippy 'who hurt you?'

Man or woman, relationship or not, irrespective of your mood, please let’s not forget to stay mindful of other people’s feelings no matter what.

42. Is that how you are going?

We all know fashion isn’t like a super-strong suit for an average guy, even married women still find it hard to get their husbands to dress better sometimes. While most men will listen to their girlfriend’s take on their outfits, some don’t welcome criticisms quite as easily.

Either way, the goal is to constructively share your ideas while leaving room for choice because the decision to look better or not is ultimately his. ‘Is that what you are wearing?’ will only make him feel self-conscious all day, and I can’t imagine he’d appreciate that much.

43. Have you ever killed? Would you?

This question might not be so out of place if you ask an inmate already serving time, but it would do a number on a regular guy on the outside. Unless you are playing a game and looking to go real dark, I recommend shelving this one too with the questions you should never ask a guy.

44. How often do you watch porn, and what type?

We’ve seen the statistics of how men love their porn – frequent and hardly vanilla. In their defense, there is only so much the plain stuff can do for you before you get tired, so if your guy watches adult films a lot, chances are he’s exploring some messed-up categories.

Does this mean he wants to dissect and analyze his attraction to taboo with his woman, though? Most likely not, so if you won’t join him, back off. 

45. Would you let your best friend watch us have sex?

Speaking of, most of our fetishes and fantasies come from what we watch, but I doubt that would make it any easier for guys to have the conversation in real. If you must share a controversial fantasy like that, keep it hypothetical. 

Even if he’s the one who suggests a threesome, bringing up his close friend as a potential candidate plants doubt, jealousy, and a host of other things that will do your relations no good.

46. Who are you texting?

They say a woman knows these things, whether it’s when her child is crying or her man cheating on her. It sort of comes with the territory when you’ve either been cheated on by a guy or know someone who has.

However, you can’t use that as an excuse to let paranoia drive you. He may not be stepping out on you, but you just might push him to it if you keep asking who just called/texted your boyfriend.

47. Do you think you can marry me?

First of all, you don’t ever want to make it look like a guy is doing you a favor by marrying you, and asking him this way sort of appears that way. There are better ways to tell your bf you want to get married when the time is right than to put it like this. Emphasis on when the time is right because discussing marriage and kids prematurely tends to freak boys out. 

48. Questions that come off as nagging.

“Why haven't you,” “won't you,” and the thinly-veiled, “I thought you said” questions when you want to get your man to do something. Believe me, they see through it all, a traditional guy might even call them emasculating. You want your husband to do more around the house or something, there are better ways to phrase that, I think.

49. All and every question you don't want the answer to.

Finally, if I were asked to put this entire list in a statement, it would definitely not be to any of those questions you know deep down you don’t want to be answered. Save both parties the stress, awkwardness, and whatever other feeling comes with such probes, and maybe we all can live happily ever after. 

FAQs

What’s the worst question to ask a guy?

The worst question you can ask a guy depends on context, but generally, it should deviate from what he’d expect you to ask. It can be something so dumb or embarrassing it kills the mood or just something outrightly offensive.

What are some uncomfortable questions to ask?

Questions like “Are you sure you are [not] gay?” “How much money do you make?” “Thoughts on adults dating teens” and “what are we?” can make people uncomfortable depending on their threshold and how close the person asking is to them.

What are interesting questions to ask a guy?

What passes as interesting depends on the context of the conversation and what you are trying to achieve. If you want to get to know a guy you like, open-ended questions about him and what he likes might do the trick.

What are some flirty questions to ask a guy?

The best flirty questions to ask guys are those who strike a balance between ‘out there’ and subtle, of course, you can always adjust the intensity as required. For instance, there is a lot between ‘do you work out often?’ and “what’s the worst sexual thing you’ve ever done?” even though they are both flirty.

What are some juicy truth questions?

“What’s the most embarrassing thing you’ve ever done?” “How often do you cry?” “What are your wildest fantasies/fetishes?” “Have you ever been arrested, what for?” “What are you most insecure about?” etc.

Key Takeaways

We’ve all asked at least one of these questions before. If they didn’t yield much with your ex, why would you expect them to have a different result in your current or next relationship? And on the off chance that you’ve been in love and never asked any of them before, keep it that way, why don’t you? You’re really not missing out on anything but awkwardness. 

Either way, let me know your thoughts on the list and share the article if you liked it.

You may also be interested in: 3 Easy Ways to Find Out If He's Cheating On You

Sonya Schwartz
A hopeless romantic that struggled for many years to find her Mr "Right" and made all the mistakes you could think of while dating. Known for always choosing the wrong guys or messing up relationships, Sonya was finally able to change her approach and mindset when it came to dating which helped her eventually find the man of her dreams and become happily married. You can read more about me here...

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