32 Awkward and Weird Questions to Ask A Guy

Every conversation requires a solid foundation of wit and intelligence, which are needed when asking awkward and weird questions. For some people, asking awkward and weird questions may come naturally; but it is not always the case, especially when a lady is trying to start a conversation with a guy.

Asking a guy weird questions helps to break the ice, while awkward questions help put him in the mood to talk because guys mostly just require a little nudging with the right questions to start an interesting conversation. However, knowing the right type of questions to ask, is not a very easy task because such questions could easily become offensive if discretion is not applied. Nonetheless, the right type of awkward and weird questions to ask a guy upgrades your conversation-making skills, as well as improves your wit.

We have carefully curated 32 awkward and weird questions to ask a guy, you can choose from or give you an idea of the kind of questions to ask. However, there are certain factors to consider before asking a guy awkward/weird/embarrassing questions.

32 Awkward and Weird Questions to Ask A Guy
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Tips For Asking the Right Questions 

Humor: Ensure that your questions are humorous and the guy you are asking has a healthy sense of humor.

Privacy: The questions should not be about very private aspects of his life that you are not sure he is comfortable sharing.

Build trust: Most guys only open up to a person they trust, especially when it comes to really awkward questions, so before you go ahead to ask really dicey questions, ensure that a certain level of trust has been established.

Discretion and boundaries: Some questions can only be asked by a wife or a lover, so if the guy is just a friend, it is not just any kind of awkward or weird question you can ask him.

Be open to sharing: Ensure that you are comfortable enough to answer the same question in case he decides to throw it back at you.

Conducive environment: Do not pick just any random location to ask the questions. Ensure the environment is comfortable and conducive enough for him before you ask.

Do not pressurize: If he is not willing to answer the questions, do not press or pressurize him for an answer as it may send off wrong signals. Be patient.

No Judging: Accept the answers without judging him for his response or using his answers against him.

Forewarn him: Before you start asking awkward and weird questions, inform him that you are about to ask him such questions and if he says he is comfortable enough, then you can go ahead.

Moderation: Do not ask so many awkward/embarrassing/weird questions at the same time. It will give off a wrong signal.

Be polite: Make sure your questions do not sound rude or condescending as they may escalate into a bad argument.

Be spontaneous and creative: Especially with weird questions, you can create questions from things in your immediate surroundings or from past conversations.

Listen actively: When you ask a weird or awkward question, listen actively to the response that you get, so you don’t end up repeating the question or making unnecessary remarks afterward.

Relax and have fun: That you want to ask a guy awkward and weird questions, doesn’t mean you should get into an awkward situation yourself or weird yourself out. If you don’t feel confident enough to ask the questions, don’t bother asking them. But if you are confident enough, then relax, have fun and select any of the following awkward and weird questions to ask a guy.

Weird Questions To Ask A Guy

Asking a weird question requires creativity as well as discretion, in order not to cross boundaries or sound outrightly offensive. To ask a guy weird questions, you need to be certain that he will not be offended or triggered. Here are some perfect examples of weird questions to ask a guy in order to get an interesting answer, or create an interesting conversation.

1. What is the most tasteless meal you have ever eaten?

Most guys only keep a memory of the best meal they have tasted, so asking them about the most tasteless meal they have ever eaten will catch him off guard. You will enjoy asking this question because if he is in the mood for storytelling, you will have a very good laugh afterward.

2. Would you rather reincarnate as a Lion or as a woman?

This is one weirdest question most guys may find difficult to answer but it is very necessary. You will get to find out what he thinks of being a woman. This is a very unexpected question and he may have a very hard time answering it.

3.  How long does it take to cook your favorite meal?

Only a few guys know how long it takes to prepare their favorite meal. This question will get him racking his brains as it ticks all the boxes of weird questions. If he has a favorite meal, he should know how long it takes to prepare it.

4. How many slices of pizza can you eat in 10 minutes?

Does anyone keep a timer on how many slices of pizza they can eat in 10 minutes? Find out how much he loves to eat pizza with this question, it is also weird because it is unusual to ask about the slices of pizza that a person can eat in 10 minutes.

5. Do the blind see in their dreams?

This question is one of the mysteries of the world that are yet to be unraveled. Asking a guy if the blind see in their dream is on the top ten list of the weirdest questions to ask. He most definitely will not have a factual answer, but it will be fun listening to him as he tries to come up with an answer.

6. What is the most abnormal thing you have ever done?

Has he ever done something he considers abnormal? Most people like to believe they do normal things, however, you can make him think deeply and wonder if he has done anything that is considered abnormal.

7. How many ladies have you caused a heartbreak?

This is one question he may shy away from giving an answer to, especially if you are his love interest or his significant other. However weird questions are meant to catch the other person off guard, so go ahead and ask as his answer may be a great conversation starter.

8. Would you rather have 10 wives or 10 children?

A harem of wives or a brood of children, which one tickles his fancy more?  As weird as this question is, his answer will give you an insight into the kind of guy he is. You will get a more sincere answer if the guy is simply your friend or your brother, as he may be reluctant to say his actual answer if you are romantically connected.

9. What is your childhood secret?

Most guys have childhood secrets that nobody knows. This is a weird question because he will not expect to be asked about his boyish secrets. He may or may not share, either way, you have accomplished your mission of asking a weird question.

10. How will you describe a painting that is indescribable?

This is a combination of a weird and intelligent question as it will make him put his use of words and language to test. How can a thing that is indescribable be described? We bet he never saw this question coming.

11. What will you describe as the color of water?

Still on the top list of weird questions to ask a guy. This is a creative weird question because you are not only asking him if water has a color or not, you are asking him to make a description.

Awkward Questions to Ask A Guy

An awkward question is a question that is slightly discomforting and poses a little inconvenience. When you ask a guy an awkward question, you are asking him a question he may want to shy away from giving you an answer to. However, Awkward questions for a guy help to measure how “open” he is.

Take note that, it is not advisable to start up a conversation with awkward questions as it may yield a negative effect of him losing interest in having further conversations with you. Awkward questions for a guy are better introduced when the both of you are comfortable with each other or during bonding stages or during a game of truth or dare. Here are some worthy awkward questions you should try out.

12. Would you rather urinate Gold or defecate cash?

Urinate gold or defecate cash? This will get him thinking for a moment. This is an awkward question that also tests his calculative skills. Would he rather have gold or cash at his disposal?

13. How many times a day do you think about sex?

According to research, men think about sex 19 times a day on average. Asking a guy how many times he thinks about sex in a day is top on the list of awkward questions to ask a guy. He may or may not be truthful about his answer and he may decide not to give you an answer to the question. Not every guy wants to disclose how many times he gets horny in a day.

14. How healthy do you consider masturbation to be?

This is a tricky awkward question because you are not asking him to admit to masturbation but his answer may be considered an admission, because if he says masturbation is very healthy, it may imply that he is also an active masturbator. Not everyone wants to admit that they practice self-sex.

15. What is the stupidest thing you have ever said to someone?

Have him think of all the stupid things he may have said to people and pick out the most stupid of them all. This is a very awkward question because the stupidest thing he may have ever said may be too embarrassing to share.

16. How many plates of food can you consume in a sitting?

Except for people who openly refer to themselves as “foodies”, most people will rather not talk about their feeding abilities, especially to the opposite sex. Asking him how many plates of food he can consume in a sitting, especially if you are his love interest or his crush, is a very awkward question.

17. What insect are you most afraid of?

A guy wouldn’t want to admit he is afraid of any insect at all. Being afraid of insects is considered a feminine trait, however, many guys are actually afraid of certain insects. Find out which insect he is afraid of with this awkward question.

18. Have you ever walked in on a couple having sex?

Walking into a couple having sex is a very awkward situation and asking him if he has ever walked into a couple having sex, would mean you asking him to remember a very awkward situation if he has ever been in such a situation. This is an awkward question about an awkward situation, which means double awkwardness.

19. How many lies do you tell in a day?

Not many people admit that they tell lies, so one of the most awkward questions you can ask a guy is how many lies he tells in a day. Because he wouldn’t want to paint himself as a liar to you, he will most likely lie about his answer.

20. Guess how many guys I have kissed

The question is about you, but it will surely make him feel very awkward because he will not want to hurt your feelings by naming an outrageous number, he may also be afraid to guess the correct number, especially if you are his love interest. This is one of the perfect put him on the spot type of awkward questions for a guy.

21. Are you in love with me?

If you are suspecting that a guy has a crush on you, this is one of the most awkward questions you can ask him, because you are putting him in the “now or never” spot. This question may result in him summoning the courage to ask you out. Only ask this question if you are fine with either a yes or no answer.

22. Have you ever thought of another person other than your partner when having sex?

On a list of the most awkward questions to ask a guy, this question is among the top ten. A lot of guys have thought about someone other than their partner during sex but may have a hard time admitting it. A caveat to this question is, that it is better if you ask a guy you are in a platonic relationship with to avoid hurting your own feelings.

Embarrassing Questions To Ask A Guy

Embarrassing questions are questions that are not usually asked in a regular natural conversation. Before you ask an embarrassing question, make sure you are alone with the guy and you are sure of his temperament so you don’t hurt his feelings. Apply discretion in your type of question, a helpful tip is to ensure that the embarrassing question is funny and can be easily overlooked. Do not ask embarrassing questions to the hearing of other people unless in a group truth or dare game session.

23. How many times do you change your boxers in a week?

If your intention is to make him feel embarrassed, then you have succeeded with this question. Although he may lie about his answer, he will still feel embarrassed you asked him such a question, especially if he doesn’t change his briefs very often.

24. How many times do you fart in a day?

A fart is a natural occurrence that almost everyone is shy about. Asking a guy how many times he farts in a day is embarrassing because you are telling him that you know he farts because he is a human being and no matter the response he gives you, he will still feel embarrassed about it.

25. Have you ever been caught masturbating?

This question tops the list of the most embarrassing question to ask a guy because you are indirectly getting him to admit that he masturbates, and if he has ever been caught doing it, the situation becomes even more embarrassing.

26. At what age did you have your first wet dream?

The first time most guys experienced a wet dream, it was an embarrassing and awkward situation, so, asking him the age he had his first wet dream is embarrassing, especially if he had it at an age that is considered early or late.

27. Have you ever swallowed your own vomit?

The response to this is most likely to be “eeewww” but then, it’s an embarrassing cringe-worthy question.

28. Will you kiss another guy for 100,000 Dollars?

This is embarrassing because if you ask a heterosexual male if he will kiss a person of the same sex, his answer will be no. However, it becomes embarrassing if a price tag is attached to it, because he may consider saying yes even if it is for a split second.

29. Do you pee on yourself when you shower?

Most people pee on themselves when they are taking a shower, however, it is still embarrassing, especially for a guy to be asked such a question or to admit that he pees on himself when taking a shower.

30. Will you marry me?

This is one of the topmost embarrassing questions to ask a guy. It puts him in a tight corner because he may not want to be blunt and hurt your feelings if his answer is no, plus it is not every day that a lady proposes to a guy even if it is a joke.

31. What is the most embarrassing thing you have ever done?

Having a guy recount the most embarrassing thing he has ever done is in itself embarrassing. He will become embarrassed all over again.

32. Have you ever lusted after a friend’s girlfriend?

Most guys may never admit that they have lusted after their friend’s girlfriend and it will be very embarrassing to ask them such a question, so if your plan is to make him feel very embarrassed, this question works.

Awkward And Weird Questions To Never Ask A Guy

Although awkward, weird, and embarrassing questions are usually outlandish, there are some questions you should never ask a guy, especially if he is not your lover or husband.

Financial status: Do not ask about his income or debt profile. Do not ask him how much he makes or the highest he has ever earned. This question is reserved for couples.

His sexual prowess: This is especially for a guy you are in a platonic relationship with. It gives off the wrong signal and he may assume you are asking him as a form of invitation.

Health condition: If he has a visible or a known health condition, do not ask any weird or awkward questions about it.

If he is comfortable with the size of his private part: This is a no-go area as it may trigger insecurities. A lot of guys are insecure about the size of “down there”.

Past Traumatic Events: Do not ask about how a loved one died or any of his personal harrowing experiences, it is not good for his mental health. Traumatic experiences should be avoided.

Body size: Avoid questions like “why are you so fat or why are you so skinny”. It is akin to body shaming.

Body Count: Except he offers to tell you himself, you shouldn’t ask him how many women he has slept with. He may not be honest with you, so there’s no need to ask. Plus, except you are his health professional, it is not your business to know.

If he is a mummy’s boy: There is absolutely no need for this question. Even mummy’s boys do not admit to it and he may find the question upsetting.

…In conclusion, awkward and weird questions to ask a guy are meant to create interesting, expository, and fun conversations. They are not intended to offend, malign, or invade a guy’s privacy. Weird questions are advisable on a first date, but awkward and embarrassing questions should be saved for later when there is some level of familiarity.

Princess is a writer and an enlightened being.


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