awkward questions to ask a guy

59+ Super Awkward Questions to Ask a Guy

Looking for some Awkward Questions to Ask a Guy? Asking a guy embarrassing questions is incredibly personal. One person may not find something embarrassing while another does.


59+ Super Awkward Questions to Ask a Guy

awkward questions to ask a guy
awkward questions to ask a guy

However, if you’re not in the correct stage of your relationship to talk about them, asking very personal or intimately probing inquiries can be embarrassing for you both.

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Questions to Never Ask a Guy

Even though certain questions are embarrassing for both the guy and you to ask, you might want to know the answers, especially if the inquiries are related to commitment, feelings, and the future of the relationship. However, it might not be wise to approach them directly.

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When did you last experience tears?
How many guys do you think I’ve slept with?
Have your mother, sister, or grandmother ever been exposed?
Are you certain that you are not gay?
Would you enjoy a beer belly?
How much time do you spend getting ready for a date?
How many girl’s phone numbers do you have?
Can I change your appearance?
What sum of debt do you owe?
Have you thought of getting plastic surgery?

Pushing the Limits

The most embarrassing inquiries are those that go beyond the bounds of propriety and taste. You are more likely to humiliate one or both of you if you urge someone for an answer, especially one he or she may not want to give.

Have you ever gravely hurt or murdered someone?
Have you ever been put in jail?
Would you ever watch illegal p*rn?
How would you murder me if you wanted to?
Would you allow me to (insert an explicit and odd request)?
Have you ever thought a kid was cute?
Do you find teenage girls attractive?
Guess my age, do you?
What do you estimate my weight to be?

Relationship Tips

Questions for an embarrassing first date

First dates and blind dates are uncomfortable enough without the stress that comes from poorly phrased inquiries. Stick with safe topics and steer clear of these awkward inquiries if you want to go on the second date.

Do you cherish me?
Do you believe that you could love me?
Does this give me a large butt?
Am I ugly or fat?
Do you have enough cash to cover the date’s costs?
How much money do you now have in your bank account?
Why did you break up with your previous girlfriend?
How many partners have you had in bed?
Do you intend to marry someone?
Do you intend to have kids?
What has ever happened to you that you find most embarrassing?
Have you ever had an STD?

Questions to Avoid Asking Your Boyfriend

What turns a boyfriend off the quickest? asking him uncomfortable or intrusive questions before your connection is ready. Beginning with the first date, every relationship undergoes a personal growth that could lead to marriage and parenthood or end two weeks later. Based on their unique emotional baggage and chemistry, each couple experiences this personal journey at a different level.

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Do I kiss better than your ex-boyfriend?
Why do you want to date me?
When you’re with me, do you have thoughts of your ex?
What one thing about my body would you change, if you could?
What kind of engagement ring price range can you afford?
Is my importance greater than your mother’s?
Would you forego your friendships to join me?
Which of my buddies do you consider to be the sexiest?

Questions To Start A Conversation That Are Weird But Work

Strange inquiries with a high risk of embarrassment can occasionally be entertaining conversation starters. These queries can lighten the mood even though they seem a little uncomfortable when spoken. Look for quirky subjects that won’t require him to go into great detail about his emotions or tales.

What is the likelihood that you would hold a world record if you did?
What kind of insect would you be if you could?
Where are you least likely to travel in the world?
Which app are you unable to live without?
Would you be able to live without your phone?
Which game, if you could play it, would you choose?
How many hours a day would you be awake in an ideal world?
Which grade would you return to if you could, if only for a year?

Confusing Questions

Numerous of these inquiries are merely curiosity that might or might not be raised in casual conversation. When in doubt, consider how you would react if the same question were posed to you. Don’t ask it if your face starts to burn and you start to get butterflies in your stomach.

Relationship Tips

Being curious about a guy you have just started dating is only natural. Furthermore, even if the relationship is brief, you should be aware of some details, such as his sexual background—no one wants STDs! It might not always be simple to come up with a list of awkward questions to ask a guy. If you’re unsure of which inquiries to make and which to omit, we strongly advise that you read over the list we came up with.

You can always share embarrassing information about yourself to help people feel more at ease sharing private information. You will either become closer after opening up to each other and realizing it won’t work out, or you will recognize it won’t work out and split ways amicably before things get too messy. So stop overthinking it and start asking the things you want to ask a person you are dating or want to date.

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35 awkward questions to ask a guy, some of them are embarrassing

Questions that are awkward or uncomfortable might be challenging since everyone wants to get out on the right foot. Once you are both at ease with one another, it is crucial to be open and honest because, after all, what kind of relationship is there without honesty? Make a list of all the awkward questions you could possibly ask a guy, take a drink of liquid courage, and then say it!

Give him room, though, if you see that he’s becoming uneasy. He should be allowed to decline certain inquiries; you can always bring things up later, when you two are more intimate and able to be more honest with one another.

Have you ever cheated on someone?

One of those uncomfortable inquiries to SMS a guy is this one. It is appropriate to inquire if you have abandonment issues or have experienced betrayal because cheating is a major problem. Additionally, you learn if the man is faithful or if he has a tendency to overindulge and fabricate justifications for cheating.

2. What are your thoughts on moral non-monogamy?

Some dating apps today provide you the opportunity to state your position on monogamy. It’s critical, in our opinion, that you both agree on this so that neither of you is harmed in the future. Because non-monogamy is still not common, this is one of the finest embarrassing questions to ask a guy in truth-or-dare mode.

3. Have you recently had a STI test?

Since STDs are still a taboo subject, inquiries regarding them make for some of the best awkward questions to ask a guy in a truth-or-dare format. This is why the truth or dare game can bring up this subject. If you want to safeguard yourself against sexually transmitted illnesses, you must ask this.

4. What annoys you the most?

It can be strange for a guy to reveal his quirks to you, but if you want to have kinky sex with him, you need to talk to him about it. If you are an adolescent, we advise you to skip this one because it isn’t even one of those embarrassing inquiries to make of a young man who has only recently begun to explore sex.

5. How much sexual experience do you have?

When you ask him about his sex(perience), be careful not to be judgmental. Most males are afraid of being judged for being virgins or for having a lot of sex partners. Because teenagers are typically discovering sex at this age and are somewhat insecure about their abilities in the bedroom, this may also be one of those embarrassing topics to ask a young boy.

6. What is your height?

This particular query puts an end to any awkward text conversational queries you may have had. Consider asking this embarrassing inquiry if size is important to you or if you are only interested. Just keep in mind that it’s a sex myth that being too big or little interferes with having good sex, and don’t body shame him if he is either too big or too small for you.

Relationship Tips
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7. When did you last shed a tear?

One of those uncomfortable inquiries to ask a guy you like is this one. Due to pressure from society, most men find it difficult to communicate their emotions. Your ability to deal with him depends on how sensitive or emotional he is, which will be indicated by his response.

8. How do you envision our future?

You need to know if he shares your relationship goals if you’re serious about him and hope to be married or have a long-term relationship with him. This is yet another uncomfortable question to ask a guy you like. Heart-related issues are challenging!

9. Would you date a childless person?

It can be awkward to inquire about wanting children at the outset of a relationship. However, if you are a woman without children, it is better to understand what your future partner feels about having, or in this case, not having, children.

10. What do you think of a parent dating someone?

Most guys will find it difficult to date someone who is a parent, especially if they have never been a parent. Some guys don’t mind it at all, while others do. Before you go serious, you need to find out which group your partner is a part of.

How frequently do you m@sturb@te each day?

If a young man asks whether m@sturb*ting is common, this may be one of those unpleasant topics to ask. Try not to be judgmental if he is open with you about this, and if he has a p*rn addiction, encourage him to seek treatment.

Do you cherish me?

This might be the most awkward question of them all, especially if he struggles to explain his feelings. If he takes a moment to respond to this, try not to get upset. Not everyone feels at ease making verbal declarations of love.

Sometimes difficult or unpleasant inquiries help to break the ice and introduce some worthwhile conversational subjects. But when posing the aforementioned queries, avoid being rude or overly nosy. Determine your motivation for asking first. Ask away if you want to spice up your relationship, but keep in mind that not every male will respond well to all of these inquiries. If you go too far, some people could feel frightened or just plain annoyed. We hope the list of uncomfortable questions to ask a guy above will be helpful and allow you to get to know your partner on a deeper level.