35 Awkward Questions To Ask A Guy (Some Are Embarrassing!)

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It is but natural to be inquisitive about a guy you have just started dating. And even if it’s short term, you need to know about certain things like his sexual history because who wants STDs! Making a list of awkward questions to ask a guy might not be always easy. We encourage you to go through the list of questions we came up with if you are confused about which questions to ask and which ones to skip.

You can always reveal embarrassing stuff about yourself to make them more comfortable about sharing personal stuff. And either of the two things will happen – you will get closer after becoming vulnerable with each other, or you’ll realize it won’t work out and amicably part ways before it gets too messy. So, don’t think too much and get on with the questions to ask a guy you are dating or would like to date.

35 Awkward (And A Few Embarrassing) Questions To Ask A Guy

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Awkward and embarrassing questions are tricky because initially, everyone wants to make a good impression. However, it’s important to be honest and candid once you are comfortable with each other because what’s a relationship without honesty? Make a list of all the probable awkward questions to ask a guy, down some liquid courage and drop the bomb!

However, give him space if you feel that he is getting uncomfortable; he should have the option to skip certain questions; you can always come back to them later when you’re closer and easily able to open up to each other.

1. Did you ever cheat on anyone?

This is one of those awkward questions to ask a guy over text. Cheating is a serious issue, So, it’s a valid question to ask if you have abandonment issues or have been cheated on. Also, you get to know if the guy is loyal or he is someone who gets carried away easily and comes up with excuses to cheat.

2. What do you think about ethical non-monogamy?

These days some dating apps give you the option to reveal your stance on monogamy. We think it’s important to be on the same page about this so that later on, neither one of you gets hurt. This is one of the best awkward questions to ask a guy in truth or dare mode, because non-monogamy is still not mainstream.

3. Do you have a recent STI test?

Questions about STDs are also one of the best awkward questions to ask a guy in truth or dare style, because unfortunately STD is still a taboo topic. That’s why this topic can be introduced in the truth or dare game. You definitely need to ask this, if you want to protect yourself from sexually transmitted diseases.

4. What are your kinks?

It can be weird for a guy to open up to you about his kinks but you need to have a conversation about this if you are planning on having kinky sex with him. In case you are a teenager we think you should skip this one – no, it doesn’t even fall under the category of one of those awkward questions to ask a teenage guy who has just started learning about sex.

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Related Reading: 30 Questions To Ask A Guy You Are Dating

5. How sexually experienced are you?

awkward questions for teenage guys
Ensure you are not judgemental when you are asking him how much sex(perienced) he is

Most guys are worried about being judged for being virgins or someone with a huge number of sexual partners. This one might also be one of those awkward questions to ask a teenage guy because that’s the age when teenagers are usually discovering sex and are sometimes under confident about their bedroom skills.

6. How big are you?

If you have been wondering about awkward questions to ask a guy over text, this question right here seals the deal. If size matters to you or you are just plain curious, then you might consider asking this awkward question. Just remember that it’s a sex myth that size comes in the way of good sex and oh, don’t body shame him if he is too big or small for you.

7. When was the last time you cried?

This can be one of those awkward questions to ask a guy you like. Most guys have difficulty expressing emotions due to societal pressure. His answer will give you an idea about how sensitive or emotional he is and whether you need tons of EQ to deal with him.

8. Where do you see us in the future?

If you are serious about him and want a long term relationship or marriage down the road, then you need to know if he shares the same relationship goals as you. This is again one of those awkward questions to ask a guy you like. Matters of the heart are complicated!

9. Would you date someone who is childfree?

Asking whether one wants children at the very beginning of the relationship can be plain awkward. But, if you are a childfree woman, then it’s better to know what your potential significant thinks about having or in this case – not having children.

10. What do you think about dating someone who is a parent?

Dating someone who has a child will be challenging for most guys especially if they have not experienced parenthood themselves. Some guys are perfectly cool with it; some aren’t. You need to know which group your guy belongs to before you get serious.

11. How many times do you masturbate in a day?

This can be one of those awkward questions to ask a teenage guy especially if he wonders whether masturbation is normal. If he is candid with you about this, try not to be judgmental and encourage him to get help if he has a porn addiction.

12. Do you love me?

This can be the mother of all embarrassing questions; even more so if he has a hard time expressing his emotions. Don’t be touchy if he hesitates to answer this one. Not everyone is comfortable with professing love through words.

Related Reading: 100 Questions To Ask Your Boyfriend

13. Have you ever had a one night stand?

Sorry, this is again one of the most awkward questions to ask a guy but it NEEDS to be asked. In today’s date when casual sex is so common, it is natural to have hookups be a part of your sexual history. However, if he reveals that he had many, it’s time to follow up with a question on STDs.

14. When did you lose your virginity?

Many people seem to think that there is a standard age to lose virginity. However, if you feel this is entirely subjective, then it would be fun to ask him this and get to know about his first intimate experience. Irrespective of the answer, we definitely think this tops the list of awkward questions to ask a guy.

15. Do you go to therapy?

It could be one of the most awkward questions to ask a guy as mental health is a sensitive subject. Tread carefully with this one and be kind and empathetic if and when he shares his mental health struggles with you.

16. Did you ever have any sort of an addiction?

Drug, alcohol and sex can be vices that some people can’t get enough of. Usually, it’s a negative coping mechanism and stems from some kind of trauma. Sexual abuse for instance can cause intimacy issues. If he answers in the affirmative, offer support and try to be understanding instead of being critical at the get-go.

Related Reading: 8 Ways You Can Help Your Partner Get Over Drug Addiction

17. What would you say if I told you I am pregnant?

Thinking about awkward questions to ask a guy in truth or dare? This one could give him a mini heart attack especially if he is not ready to be a Dad. Make sure you serve some alcohol before you pop the question.

18. Have you ever been attracted to a guy?

They say that sexuality is fluid and so if he answers yes, don’t be surprised. If he vehemently nods his head, ask him whether he has explored LGBTQ dating apps. Also worth noting is that sometimes a passionate denial can indicate homophobia or repressed homosexuality.

19. What is the first thing you noticed about me?

If you wore a revealing dress on your first date, and he couldn’t take his eyes off of you, then this could easily be deemed as one of those awkward dirty questions to ask a guy. Most people stick to eyes and smile; so it would be fun to know what he thinks and if he comes up with an offbeat answer.

20. What if I cheated on you?

We think you should tread with this one carefully. This question which falls under the category of awkward questions to ask a guy you like will also reveal if he is rigid in his outlook or if he understands that the world is not all black and white.

21. Would you want to experience childbirth if you could?

Childbirth is no doubt a painful process; therefore even if he says no, don’t take it personally. In case he says “Yes”, then it could lead to some interesting conversations about side effects of pregnancy as a couple. It’s one of those awkward funny questions to ask a guy as the very idea is so absurd.

Related Reading: The Ultimate Funny Online Dating Questions

22. Have you ever sent someone nudes?

Uh oh, one of the most awkward questions to ask a guy. Exchanging nudes is quite natural in sexting. And if you are into receiving solicited naughty pictures from your lover, then this question makes sense. However, make sure both of you know what cyber safety experts say about it.

23. What do you think about starring in an OnlyFans video?

If your boy has a good physique and is well-groomed, ask him what he thinks about being a participant on OnlyFans. We also think that this becomes one of those awkward dirty questions to ask a guy the moment you come up with a follow up question based on his reaction – whether he subscribes to content on OnlyFans or any other such site.

24. Have you ever ghosted anyone?

Ghosting is a common phenomenon in today’s online dating world. People do it for a variety of reasons and so don’t get anxious or lose your sanity if he says he has committed the cardinal sin of ghosting. We suggest you get to know his reason for doing so and then decide if he is worth keeping.

25. How many girls are you talking to apart from me?

Sometimes when you have just started to date someone, you like to keep your options open. Find out if he is one of those guys or if he believes in giving his best to one person at a time.

26. Is it intimidating if a woman makes more money than you?

More and more women are becoming financially empowered these days. So, it would be interesting to discover whether he can live with the changing times or if his ego will be bruised.

Related Reading: When The Man Is The Only Breadwinner And The Wife Refuses To Pitch In

27. Would you choose love over career?

Are you someone whose choice in partner leads to making or breaking their career? More often than not, we see women forsaking their careers for a man and settling with him wherever he is. It would be interesting to get to know his take on this. If he is being practical and chooses ambition, then ask yourself if it’s a deal breaker.

28. What’s your favorite physical feature in a woman?

Some guys have a thing for butts, breasts or thighs. Some even love a big woman. If your guy turns out to be one of them, then it is easily one of the more awkward questions to ask a guy because very few would admit that they like those unless they are really comfortable with you.

29. Have you ever stalked a girl on social media?

If you have been searching for awkward funny questions to ask a guy, think about this one. When you are infatuated or obsessed with someone, you tend to be curious and want to know everything about them. You might have also stalked a crush or an ex; ask him if he is “guilty” of doing the same!

Related Reading: 15 Steps To Get Rid Of A Stalker And Be Safe

30. Do you care about your partner’s body count?

Some men don’t like it if their partners have a large number of sexual partners while others are fine with it. This question will give you the perfect opportunity to understand if he is open-minded about these things or if it bothers him to have a partner with a high body count.

31. Would you want to sleep or date a virgin girl?

Many men have a fantasies of deflowering a virgin woman, while others couldn’t care less if their partner is going to be a virgin bride. If you are a virgin and are worried that your partner will expect you to be experienced, then this is one of the awkward questions to ask a guy.

32. How would you react if a girl makes the first move?

Some men complain that women don’t make the first move. If you don’t fit the stereotype and like to take initiatives in love and lust, then this question is justified. Since this is not one of the run-of-the-mill questions, it can be considered to be one of the slightly awkward questions to ask a guy you like.

stalking on social media
Asking him if he has stalked a crush or an ex on social media can be an awkward funny question!

33. Who pays on the first date?

Who should pay on a date — the million dollar question! Some things are totally dependent on culture, upbringing and financial status. Some men think it’s chivalrous and macho to pay on the first date and some think that splitting the bill is ideal in the scenario. So, make sure you are on the same page about this.

34. What turns you off in a woman?

It could be a body part or a personality trait. If you are conscious about yourself or plain curious about your guy’s turn-offs, then by all means satiate your curiosity.

35. Would you give me a massage?

Ah, this one is definitely one of those awkward dirty questions to ask a guy especially if it’s asked during the stage where you are assessing him as a potential partner. Don’t overthink this though and ask away if you think that something offbeat like a tantric massage would spice up your sex life with him.

At times, awkward and embarrassing questions break the ice and open up some interesting topics for discussion. But, don’t be confrontational or too nosy while asking the above questions. First, decide the reason for asking. If you want to add spice to your relationship then by all means go ahead and ask but remember that all these questions may not work for every guy. Some might get intimidated or just plain annoyed if you overstep the boundaries. We hope the above list of awkward questions to ask a guy will come in handy and help you get to know your guy inside and out.

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