30 Awkward Questions To Ask a Girl


There are some topics that are considered to be mundane to be discussed in a relationship. These include the topics on career, physical attributes and others. Here is a list of the things that guys want to ask you about but find them embarrassing.

  1. How many men have you slept with?

No woman want to accept that he has slept with more than one or two guys. This makes it one of the topics that you will not get an honest answer. The girl will give you an answer based on the fact that she will not want to give a number that is too high so that you do not consider her as a prostitute.

  1. Have you ever being attracted to another girl?

This is an awkward question as she will consider that that you have seen her acting more or less like a lesbian. Even if she has ever being one, this is a question that is best left for her to discuss at own volition.

  1. Do you find any of my friends hot?

Asking her this will amount to putting her on the spot. This is because she may not want you to know that he admires your friend who drives a BMW. On the other hand, saying no may make her look as if she is insulting your friends.

  1. Would you engage in anal sex or a threesome?

No matter how kinky you find the question to be, it can be quite difficult to ask any of these questions. This is because she will likely take offence when asked on these topics?

  1. Have you ever had a penis that is bigger than mine?

This is question that is likely to run in your mind especially if her ex was an NBA player. However, this is likely to cause her embarrassment and anything about her past sexual experience is something that she wouldn’t want to discuss with you.

  1. What is the craziest thing that you have ever done?

There are men who will not be afraid to ask this question. However, this is not a question to ask especially on a first date because you are likely to come out as if you are only after sex. This question can make you appear disrespectful to her.

  1. Are you having periods?

When you find a woman PMS-ing, it is obvious that she has period. However, asking her this will create an awkward situation that can be best avoided.

  1. Can we do it when you are on periods?

Many men would not mind having sex even when she is on her periods. This is particularly the case since there are ways of having sex while on periods without causing a mess like having shower sex. There are also those groups of men who do not mind the little blood. However, women will find this question disgusting to answer.

  1. How do you find my underwear?

One of the oldest question is on whether to choose the briefs or boxers. However, it can feel weird having to ask your partner when she loves whatever you are wearing.

  1. Between me and your ex, who is better in bed?

While you can phrase this question to sound better, there is no time that is the right one to ask this question.  When a man asks this question, he is trying to find out about his prowess in bed.

  1. Can we share the bill?

Many women would prefer the man to pay for everything during a date especially if it is the first one. When you get into a relationship, it can be safe to start assuming that she should pay for them. The question in the minds of most men is on when to ask these questions but most of them do not have the confidence to ask these. This is because the question will devalue themselves as the provider. Women are not also likely to be pleased answering this question.

  1. Have you ever suffered from an STD?

This is definitely one of the questions that can be quite embarrassing to answer. One reason for this is that it will look more like an accusation and nothing can be a turn off than having to discuss infections, warts and discharges.

  1. Have you ever been a drug addict?

This is another question that can break your relationship even before it starts. This is because it is definitely a touchy subject for most people.

  1. Do you find me hot?

No girl will ever talk of this especially if the answer is negative. Contemplating how attractive you are can make the woman come off as insecure, narcissistic, needy or just insecure.

  1. Can we do it without a condom?

This will not only sound impolite but it will also look irresponsible and it is better avoided. This is particularly the case during the early days of the relationship.

  1. Do you love me?

This is another question that will cause an awkward situation especially when it is asked in the early days of the relationship. Unless she has started showing the signs that he does, you can be assured that the answer will be a no.

  1. What plans do you have for our future?

This is an important question at one point. However, it is almost certain that it will be an awkward one.

  1. Have you added weight?

This is another question that girls will find embarrassing. If you think that she has added weight, you can find another better way of telling her so.

  1. What would be your reaction if I caught you having sex with another dude?

This is an embarrassing question because it will imply that you think she is cheating

  1. Have you being paid for sex?

Unless you are dating a former prostitute, this is another awkward question that will cause her untold embarrassment

  1. At what age did you lose your virginity

This is question that many girls would like to ask. However, it can cause a lot of embarrassment especially when asked in the early stages of the relationship

  1. Have you ever tried using sex toys?

This is an awkward question that you should avoid asking a girl.

  1. Why are you not seeing someone?

This is a question that will seem to create an impression that there is something that she is hiding that is making her not to find a partner. She will also find it awkward having to explain why she hasn’t met Mr. Right.

  1. Am I the kind of guy that you are looking for?

Some questions are better left unasked and this is one of them. If you ask it early enough in the relationship, you are likely to get a negative answer.

  1. What is your current salary?

Whether asked to a guy or girl this is always an embarrassing question. This is because it will make you come out as money minded person. It is advisable to wait until she is ready to share some of these details with you.

  1. What period of time do you think we need to date before we get married?

While this is a varied question, it is important to know the right time for asking it.

  1. What is the craziest thing that you have ever done?

Some things are best left unshared. Definitely she has a secret that she has kept for herself and is not ready to share with you since she may find this embarrassing or she will think that you will have a bad opinion of her.

  1. How many guys have you dated before?

This is a tricky question for most ladies. This is because most of them will not want to accept that they have dated more than 3 guys. So you should expect an answer of between one and three. However, one thing that you can be assured is that she will find this question an awkward one to answer.

  1. If you had an opportunity to choose between money and love, what would you choose?

It is a fact that most girls love men who are financially stable. Asking her this question will leave her in a awkward situation as she will not want to accept that she love men for the purpose of money rather than who they are. This is a question where you should expect to hear that she would choose love when what she means is the exact opposite.

  1. Who broke your virginity?

Girls don’t love discussing their sex life and this is one question that she will find awkward to answer. This is because virginity is the best gift a girl would ever give a man and this will leave her embarrassed that the man who broke her virginity left her.

If you want to take your relationship with her to the next level, it is advisable to avoid asking these questions.


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