Awkward questions every guy wants to ask you


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sleep with me

There are certain things guys can’t ask girls, rather shouldn’t ask. But that doesn’t mean it doesn’t linger in his head occasionally. It is surprising how some things nowadays has taken a whole new twist. Talking about sex was a taboo back then, but now people know it isn’t an untouched topic. There are many things a guy wants to ask you, but refrains from doing so, because you (girls in general) may take certain easy things, too sensitive and some sensitive things, too easy.

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 are still in the dating phase.

Why guys do not ask you questions, generally?

Human beings are curious, no matter what! Your guy wants to know everything about you, but abstain from doing so, because of you. How open or not you are, depends on what he can ask or not to you. He is actually scared if his questions would trigger you and you may go into the offensive mode. So, he plays it safe. You on the other side, play it safe too. You skip the important point and beat around the bush. Guys have only one question in mind when they hit the bed and they are mostly sexual. It doesn’t matter if he is the most decent guy, he has one question that lingers is his mind.

So here are a compilation of some questions, guys generally want to ask girls but never do!

1How many guys have you dated?

How many guys

This is a tricky question that is generally in a guy’s mind, but desists from asking. The guy never knows how you would take it in the first place. A lot of women don’t want to discuss such personal details if the relationship is pretty new. Men are more susceptible when it comes to numbers and may flip. Girls should know something! While most men think it marks a woman as a flight risk with the number of guys she has been with, some guys like the feel that the woman has experience and is quite a grown up, So not all guys are weird when they ask you that question.

2What is the wildest thing you have ever done with your ...

your ex

This question might not be the most awkward kind of question, but girls do take offense even to this at times. Many men aren’t actually afraid of asking this, but it might not be one of the favorite ones among girls during the first few dating phase. If a guy asks you this on the first date, then take offense because he is simply looking at having sex with you. Try and see if he is asking you all this, after developing a relationship. Other times, it is just to gauge the level of adventure you are ready to go to. They generally don’t ask this since they know this might come off as disrespectful in some occasions.

3Is my penis the biggest you have ever had?

The biggest

While this question is way too sleazy to ask a girl, a guy wants to know if he was the best you have been with. If the guy knows that you have been dating an NBA player, he will not dare to ask you this question. But if he is unaware, much on those lines, he would want to know if he has been the best so far. Most of the time, though, this question might not be asked because he is scared of the answer. It might be a yes or a no! If it is a Yes, chances are that you are going to get a great treat that night. If it is a NO, he will be scared of the insecurities he will have to face. As girls, if you genuinely want the guy to feel better, it is fine to say good stuff about his ‘stuff’ sometimes!

4Are you going to sleep with me tonight?

sleep with me

Let’s face it! Guys scan through your body, mind, almost everything in the first few meets. Whether or not, you give out signals of wanting to have sex, they would want to know if you would want to anyway! If they respect a woman they like, obviously that would be in the back of their head and they would wait until you get comfortable. But, oh boy! Do they really wait!?

5Do you want to do it on your period?

Do you want to do

Many! Believe me, many of them are not grossed out on the fact of you having periods, if they get sex! There are many ways to have period sex that are less messy, such as shower sex. Guys do not mind a little blood if they get what they want. They do not ask this question for the obvious reason! You would never say okay to that until you also think of it as a cool idea.

6Am I better than your ex?

Am I better

While most guys think about it, none, literally no-one asks this! 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.

7Can we split the bill, Please?

Can we split the bill

Most women prefer if the man pays the bill, but sometimes the guys are so vexed of paying, they just want to ask it out loud if the bill can be split. But, if the girl doesn’t take it the right way, it will be a word vomit! But as women, you should know that sometimes, it is nice to offer to pay and split the bill. There are two of you in the relationship and both of you have to bear equal amount of expenditure and not take each one for granted.

8Can we skip condom, for once?

Can we skip condom

Sexual preferences change sometimes. 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 rule that questions shouldn’t be asked in a loving and committed relationship for curiosity’s sake. 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 consider 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 you might have to rethink certain decisions. Also, you always might want to consider the fact that it is not always on the wrong note. 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.

So, if you know the guy for a long time or if you think you can just speak anything, go ahead and answer those questions for him. Poor him, but eh! You will love the session anyway! 😉

-Pavithra Ravi