20 Awkward Questions to Ask a Guy


Many guys do not love talking about themselves. This is despite the fact that there are some questions that you may want him to answer. If you are really interested in knowing more about him, you should avoid babysitting him and instead take the courage to ask all those awkward questions that he may not be ready to answer. If a guy is into you, he will not leave you just because you asked a harmless question. On the other hand, he will not stay in the relationship just because you avoided asking those personal questions. If you have chosen to play bare-knuckled, here are some awkward questions that you should ask him.

Would you rather cuddle

  1. Have you ever fantasized about engaging in sex with one of my friends?

Like you would guess, any sexual questions can always be awkward for a guy. However, this can be a question to find out the level of his commitment to you. Perhaps you should look at his body language as he answers the question to find out whether he is telling the truth.

  1. Who is your least favorite friend?

This is an awkward question because telling the guy to bash his buddy will definitely put him in an uncomfortable situation.

  1. Who was better in bed, me or your ex?

Dudes do not love talking about their exes particularly if they have to get into details of their personalities or sexual live.

  1. Who is my hottest friend?

This is another question that will make him anxious. This is due to the fact that he will be risking making you jealous or even hurting you by saying that he find one of your friends to be prettier. This is particularly the case if the friend is hotter than you.

  1. What is your weight?

Unlike what many people believe, men just like girls are also conscious about how much they weigh. When you ask them to reveal their weight, they can feel awkward especially when they are overweight.

  1. What is that one thing that you wish you could change about me

The reason why this is an awkward question is that if he tells you “nothing”, you will definitely understand that he is lying. This will leave him frantically searching for an answer that will not leave you upset.

  1. When was the last time that you wet your bed?

No guy will ever agree that there was a time when they were wetting their bed. This is because dudes have some kind of pride that will not allow them to admit something that will put them in an embarrassing situation.

  1. Why is it that you never go to the gym?

This is an awkward question because you will be implying that you do not love his figure. If he exercises, then you will be suggesting that the working out does seem to help as he is not in shape.

  1. Is there a past relationship that you regret about and why?

Dudes do not love talking about their previous relationship because they do not like spoiling the names of their exes.

  1. Would you ever cheat in a relationship?

This question will leave him asking whether he looks like the type who cheats. He may have cheated but he would never want you to know that because it will spoil his reputation

  1. What is it that you do not love about me?

You will always see something annoying that you do not like in your dude even when you love him with all your heart. While he knows that you aren’t perfect, he will not want to tell you that. This is why this question will cause an awkward situation.

  1. Can I see your parents soon?

This may not look so awkward but it is if you are the one pushing him. This is particularly when he is not ready to introduce you to them.

  1. What did you think of me the first time you saw me?

There are chances that the only thing he noticed about you is that you are pretty. And he would not want to let you know that there is nothing more that caused him to love you.

  1. What is the most embarrassing thing that you ever did?

We all have that dirty closet that we would not like to let people into them. When asked to share about them, we feel embarrassed and this is the same case with your guy.

  1. How many ladies have you slept with?

There are high chances that he has slept with a couple of girls. And the bad thing is that he knows that you will not be happy to hear that. So it will cause an awkward moment when you ask them.

  1. What is your monthly salary?

Like it is the case with sex, matters finances will always create an awkward moment. This is particularly the case when the guy has no money. If he has a lot of money, he may also think that you love him for the money.

  1. Will you marry me one day?

If you will be asking this early in the relationship, it will make him feel awkward. Even when he has those plans, he will feel awkward to answer in the affirmative. He many not even be ready to answer it now. Alternatively he may have plans to marry you but he may not be ready to talk about it.

  1. Do you love our president?

Political questions will always create awkward moment especially early in the relationship when you are yet to discuss these issues. The reason why he will feel awkward is that he will think that you may be having a contrary opinion.

  1. What makes you do that?

It is always awkward to point out something that he does. The reason why this question will make him uncomfortable is that he does it just because it is a hobby.

  1. Do you call or text your exe?

A guy will not like talking about his exe. This is another question that he will not want to answer in the affirmative because you will think that he is cheating.


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