Home Love & Relationship 14 Awkward Questions Guys Wish They Could Ask Girls

14 Awkward Questions Guys Wish They Could Ask Girls

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There are a number of things that you know not to ask a girl. First and foremost, you know not to ask how old she is or how much she weighs. While you might know the questions that you should avoid, it does not mean that you will not think about them.

The best relationships are based on honesty and open communication, but you have to know how to phrase everything properly. In recent years, more couples are becoming honest and open. People are unafraid to speak their minds. The normal taboos and stigmas that society places on certain kinds of communications are gradually starting to go away. At the same time, there are still some filters that exist. You have to know how to ask these questions the right way, or you could risk offending the girl.

In theory, no topic is genuinely off limits for conversations today. Discussing topics with your partner is even more important. If you ever want to be close, committed partners, there are some topics that you have to address. Your partner can learn a lot about you by the types of questions you ask because it shows what you are thinking about. No topic is completely off limits as long as you know how to ask it the right way and are honest about your reasons.

Some guys are still afraid of asking awkward questions from the girl that they are dating or want to date. In some cases, it makes sense to postpone these awkward questions until later on in the relationship. When this is not possible, you may need to find out the answer right away.

What Are Some Awkward Questions Guys Wish They Could Ask Girls?

Human beings are naturally curious. From finding out how to work a toaster to creating the wheel, human beings have investigated just about everything. When something confuses a human being, they want to find out what the answer is. While some answers are better left unsaid, there are other answers that you need to know.

Some guys are afraid of asking awkward questions because they are embarrassed. Other guys think that these questions could lead to an answer that they do not like. Still other guys are afraid of asking certain questions because they are worried about what the girl will think. Will she be angry? Will she think that he is crazy? Will she be offended? Guys cannot know how a girl will respond unless they ask the question, but getting up the courage to ask that question can be difficult. In many cases, guys will not ask awkward questions unless it is absolutely necessary.



No one can read a woman’s (or man’s) mind. It is important to ask these embarrassing questions because you will never know what your partner is thinking otherwise. Many of the most awkward questions tend to be about sex, although there are actually many awkward questions that can come up during a relationship.

To get started, we are going to include some of the most common awkward questions. These are about things like physical attributes, money, sex and careers. While these might be the most common awkward questions guys with they could ask girls, they are not the only ones. If we missed your awkward question, leave it in a comment at the bottom of the article.

1. Can We Split the Bill?

Traditionally, the man pays for every date. In the modern world, women are working outside of the home and having high-paid careers as well. It seems quite fair for the couple to split the date initially. At the same time, asking this question can be awkward. Once you are in a relationship, it is safe to think that the woman should pay some of the dates as well. Initially, guys may be afraid to ask because it may make them seem cheap or un-chivalrous. The best response is to not have to ask this question at all. If the woman volunteers to pay her half of the bill, no one has to ask and the couple can start out the relationship on equal footing.

2. Do We Have to Use a Condom?

While condoms help to protect you from STDs and pregnancy, some couples do not like to use them. Unless you are in a committed relationship, it is generally better to use a condom to protect both partners. At the same time, many guys want to know if they have to wear a condom or not. If the girl asks if you have a condom, it is safe to assume that she wants you to use one. No matter what though, you should have a talk about any sexually transmitted diseases before you have sex.

3. Are You on Your Period?



Despite a common misconception, premenstrual syndrome happens before a woman has her period. If you think that she is unusually moody, her period is most likely starting in a few days. Asking her if she is on her period could offend her or at least make things very awkward for you. Your best bet is to wait until later in the relationship to ask this question unless you know that your date is very open about the topic. If you are about to get busy in bed, then you can bring up the topic.

4. How Many Guys Have You Slept With?

This is an extremely difficult question for guys to ask. Many women dislike answering this question because they do not want to be judged and thought of as promiscuous. Men are more likely to judge a woman on her number of partners than visa versa. Some guys are also afraid to ask this awkward question because they do not want to know how much competition they are up against.

5. Will You Sleep With Me Tonight?

If you ask her to bed with you, then you risk offending her. If you do not ask, then you might miss out on an enjoyable night together. This is probably not a question to ask on the first date. Even if she is willing to go home with you, hold off until the second or third date because this signals that you are interested in her for more than just sex. When you do ask her, make sure you do it in a respectful way and just be honest.

6. Have You Ever Done Drugs?

This question could bring you closer together or push you further apart. Drugs can be an extremely touchy subject. If your partner is in AA or NA, they might be uncomfortable sharing that answer right away. They may also be afraid that you will view them with disgust. Either way, you are in for a difficult conversation depending on what the answer is.

7. Do You Like My Body?

You know that you are attracted to her, but how does she really feel about you? Is she just being nice or does she find you attractive? Asking a girl if she likes your butt or legs makes it seem like you are fishing for compliments. At the same time, you really want to know if she finds you physically attractive. If she is not attracted to you, then you are not going to have a relationship for long. Asking takes a certain degree of confidence, and it is difficult to ask this question without seeming narcissistic. Perhaps your best bet is to judge what her answer would be by how she acts around you or the compliments that she gives you.

8. How Does My Penis Compare?

This is one of the most common questions that guys have, but they are often afraid to know the answer. Size varies significantly from guy to guy, and it is normal to want to know how they stack up. At the same time, the last thing that they want to hear is that they are smaller than average.

9. Do You Have an STD?

While this might be one of the most awkward questions guys wish they could ask girls, it is also one of the most important. Many STDs are extremely contagious, so you need to know in advance if the girl you are dating has an infection. Not only do you not want to catch a disease, but it can also be a turn-off. While this question may be awkward, it is extremely important that you ask it. You need to find out if you should use extra protection or avoid sex altogether before you jump into the bedroom.

10. What Do You Think of My Underwear?

While girls might have Victoria’s Secret, guys tend to get boxers or briefs. For girls, this may seem like an odd question. Most of men’s clothes look remarkably similar, so does it really matter? For the guy, it does. This is another way to find out if the girl thinks her partner is attractive. If she dislikes what he wears, it is also a way for him to know what fashion-related changes he should make to become more attractive to her.

11. Do You Want to Have Sex on Your Period?

Some women and men are completely against having sex during the woman’s period. Other guys and gals could not care less. This is an awkward question to ask, but it is one way to find out if you can still have some fun during that time of the month. Some guys do not care about a little mess, but are just afraid that the girl will think they are disgusting for asking this question.

12. What Is the Wildest Thing You Have Ever Done?

This is not really an important question to ask on a first date. Unless you are talking about wild acts in the bedroom, it probably will not offend your date to ask this question. In many cases, this question can be used as an ice breaker. Later on, you may also want to find out what the wildest thing your partner did in the bedroom. In general, it is best to save that question until after you have had sex.

13. Are You Open to Threesomes, Anal Sex or Bondage?

Guys are often afraid of all of these questions. While they would love to get a “yes” answer, they are afraid that they will seem too kinky or sleazy and drive the girl away. In many cases, these questions are best left for later on after you have slept together for several months and have developed a closer relationship.

14. Am I Better in Bed Than Your Ex-Boyfriend?

This is a hard question to ask, and you are rightly afraid to find out the answer. He may have been better in bed, and you don’t want to hear that. Worse still, she could lie to you when she answers. This question makes guys feel extremely vulnerable, but it is not all bad news. Everyone is different in bed, and there is not always a better or worse partner. Sometimes, partners are different without being better.

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