15 Awkward Questions Guys Wish They Could Ask Girls

There are things you shouldn’t ask a girl. But that doesn’t mean they don’t linger on a guy’s mind occasionally. Here’s what he wishes he could ask. By Danielle Anne Suleik

15 Awkward Questions Guys Wish They Could Ask Girls

It’s surprising how more open and honest men are nowadays. They’re not as afraid to speak their mind as they were before. The filters they used to have existed because of the stigma society put on taboo topics like sex, race, gender and social standing.

These days, no topic is off limits because discussing such things has become necessary in order to form a connection with your partner.

The good thing is that you will be able to tell a lot about a person because of the questions they ask. The bad part comes when their questions feel too out of bounds.

Some topics are still off limits, not because it’s not something that should not be discussed, but some things need a certain maturity period before it can be asked.

These are the awkward questions that guys are too scared, embarrassed or confused to ask about. Some of these questions can be asked without any qualms if the guy is in a serious relationship. However, some guys are itching to ask these questions while they’re still in the dating phase.

Why don’t guys want to ask awkward questions?

Humans are naturally curious beings. When something confounds them, they will want to know the answer. It usually turns out okay since asking questions gave us fire and the wheel, but some things are considered better left unsaid.

It could end up badly and embarrass both people in the conversation. It could also open up a can of worms that neither wants to get into. A man can easily be embarrassed when his masculinity is questioned or when his sexual preferences are judged. [Read: 14 things you say or do that emasculates your man]

They are afraid to ask these questions because they don’t know what will happen when they do. Will she get mad? Will she think he’s insane? They never know what women are thinking, and that is why they don’t see the point in asking awkward questions, unless it is absolutely necessary.

Judging by the answers that most men gave when asked what embarrassing questions they want to ask, they’re usually about sex. Although sex isn’t the only important but awkward thing to talk about, it’s still the most personal and private thing you can ask a person when you start seeing each other. Asking about sex also makes a person vulnerable because it immediately showcases their own interests in the topic as well.

What awkward questions do guys want to ask girls?

Still, there are some topics that cover mundane topics like money, careers, physical attributes and others. We’ve compiled a list of those things and why guys want to ask them. It’s surprising to note how men justify these questions because some of them are exactly what you’re expecting, while some are completely baffling.

#1 How many guys have you been with? It’s hard to ask this question because a lot of women don’t want to discuss it at all. Men are more susceptible to judging a woman by the number of men she has been with, rather than vice versa. Most men usually think it marks a woman as a flight risk, a possible cheater or promiscuous, while some men find it promising because of the amount of experience a woman can showcase mentally and physically.

#2 Are you open to anal sex, a threesome or a little bit of bondage? No matter how kinky the activity is, it’s not surprising that any one of these topics will run through a guy’s mind at some point. It’s difficult to even delve into these types of subjects, because some women take offense at having to discuss something so sexual in a new relationship. [Read: 9 conversation no-no’s in a new relationship]

#3 Is my penis the biggest you’ve ever had? If a guy knows that you used to go out with an NBA player, they wouldn’t even bother consider asking you this. If, however, they have no idea what the anatomy of your past boyfriends look like, they will wonder if theirs is the biggest you’ve ever seen. They will not ask you this because they are either afraid of the answer, or they may think that you will think less of them once their self-esteem issues are out in the open.

#4 What’s the wildest thing you’ve ever done? Admittedly, some men aren’t afraid to ask this, but it’s not exactly a necessary question on the first date. If a man asks this immediately, their only goal on that date is oftentimes sex. Other times, they want to ask this because it allows them to gauge what level of adventure you’re willing to tolerate while you’re seeing each other. Men won’t ask this outright because they’re afraid they might come off as sleazy or disrespectful if they do.

#5 Are you going to sleep with me tonight? These days every man wants to ask this question on the first date. Even if a woman is not sending out signals that they’re willing to sleep with a man immediately, a man will still wonder if asking you might yield a different answer. They won’t do it if they respect the woman, but oh boy, do they want to know. [Read: 7 signs women give away when she wants to sleep with you]

#6 Are you on your period? A lot of times a woman who is PMS-ing is obviously on her period, but hormonally-imbalanced women are not much different from your run-of-the-mill pissed-off woman. A man will want to ask this just to ascertain that they can do damage control by throwing chocolate at you or going out of town, but they won’t ask for fear of pissing you off more than you already are.

#7 Do you want to do it even on your period? A lot of men are not grossed out by the thought of periods, if it comes with sex. There are ways of having period sex that aren’t as messy, such as shower sex. For other men, they simply don’t mind a little blood. They’re usually afraid to ask this because they’re assuming that a girl might think that it’s disgusting or she’s just too hormonal to even entertain the idea. [Read: Your go-to guide for period sex]

#8 Do you like my underwear? The age-old question “Boxers or briefs?” is a generic question, but asking whether your partner likes what you’re wearing is too weird of a subject. Some men just want to know whether you find them attractive in their underwear or if they should start shopping for new ones. It’s hard to ask this to a woman because it’s the equivalent of a fashion-related question, which men may often avoid. Plus, the setting for this question to be asked is when you’re both practically naked.

#9 Am I better in bed than your ex? There are various ways to phrase this question, but there is never a right time to ask it. A man may want to know if he’s doing everything right or if there’s anything he can find out about how to make himself better in bed. It makes a man vulnerable to ask this because it means that he is questioning his prowess in bed while asking you to compare him to your ex. [Read: 9 big issues on a man’s mind when having sex]

#10 Can we split the bill? Most women prefer it if a man pays for everything on the first date. When you’re in a relationship, it’s safe to assume that a woman should start paying for some of the dates. The question is when, but men are too embarrassed to ask this. Asking it makes them look cheap and may even lower their value as a provider. They just wish that women would start volunteering on their own, but some women purposely ignore this necessary dating etiquette just for the free dinner.

#11 Do you like my ass? Never have I heard a guy or even heard of a story of a guy discussing his ass – in the same approach as he does his biceps – with his buddies. Gay men, yes, but straight men, no. Surprisingly, men wonder whether women like their ass or not. It’s the equivalent of a woman wondering whether a guy likes her breasts. Guys don’t particularly focus on it in the gym like they do their arms, chest and abs, but they do wonder. The problem is it’s not something that guys are confident enough to ask about seriously.

#12 Do you have an STD? This is possibly the most embarrassing question a person can ask someone. Not only does the question seem like an accusation, but the topic of warts, infections and discharges can be a definite turn-off. This is why people should really set aside time to talk about sex before doing it, instead of immediately going at it, the consequences be damned! If a guy is too afraid to ask this, the best thing he can do is wear three condoms and get checked as soon as possible after contact. [Read: 4 topics you need to discuss and 8 topics to avoid in a new relationship]

#13 Have you ever done drugs? It can either be a point of contention or a cause for camaraderie. It’s a double-edged sword these days, and asking with enthusiasm as opposed to disgust can either make or break your budding new relationship. Guys are too afraid to ask, because it’s a very touchy subject for most people.

#14 Do you think I’m hot? Let’s face it. A guy can’t ask this without sounding unsure of himself and we all know that a man cannot handle being unsure in front of a woman. Contemplating their attractiveness also makes them come off as narcissistic, insecure or needy.

#15 Can we skip the condom? They want to ask, but it’s impolite – not to mention very irresponsible. That doesn’t mean they don’t want to put the offer on the table. It’s just not worth mentioning, when the girl immediately asks you if you do have a condom.

There is no question that cannot be asked, for curiosity’s sake, when two people are in a loving and trusting relationship. These questions, however, are rarely and almost never asked when two people have just started dating.

Even if you aren’t dating, a guy won’t even considering asking these questions because no matter what the answer is, the asking part ends up being unbearable and awkward for everyone involved.

If a man is confident enough to ask these questions without worrying about the consequences, then I applaud whoever he is. Knowing that guys have their own embarrassing questions can make it easier for a woman to feel that they are not alone in thinking awkward thoughts.

[Read: 25 topics you should talk about in your relationship]

Whether these subjects do come up or not, you can rest assured knowing that men just tend to be a little curious. These questions may be at the back of his mind, just dying to get out. However, because of his respect for you, the possible negative consequences and the possibility that you’ll think he’s insecure, he may be inclined to just let the issue slide.

Liked what you just read? Follow us on Instagram Facebook Twitter Pinterest and we promise, we’ll be your lucky charm to a beautiful love life.

Danielle small image
Danielle Anne
Those who can’t do, teach. I can neither do nor teach as well as others, but I can try. Aside from being a writer, I am also a physical therapist. My dream is...
Follow Danielle on