Women are, admittedly, quite the inquisitive bunch. We always want to know things, especially if it’s about the guy we’re dating. And sometimes, using the right kind of awkward questions to ask a guy can reveal a lot more about him, because it puts him in a spot and he wouldn’t know what to say!

Sure, we don’t want to ask a guy embarrassing questions, but sometimes it is just needed.
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Whether we snoop, spy, or simply outright ask, there are always ways to know what you really want to know! He may blush, he may laugh, but all said and done, you will have the answers that will reveal a lot about him!

[Read: 20 good questions to ask a guy and find out who he is]


Why ask these awkward questions?
What makes a question awkward? One of two things, you find it inappropriate to ask him, or he may have a difficult time answering it because he’d have an inappropriate answer.

But truth be told, awkward questions are something all of us have on our minds. You may not ask something, but you are thinking it!

And if you’re thinking it, and it’s something you’re itching to ask, why not just give it a go? It’ll be funny, and what’s the worst that could happen? He asks you the same questions back in return!

So if you do want to use any of these awkward questions to ask a guy, keep your own answers ready because he WILL ask you something similar as well. But the best part of all this, the big secrets and awkward questions will be out of the way, and you both can have a laugh at the same time as well!

[Read: 15 weird and silly questions guys wish they could ask girls]

The best awkward questions to ask a guy and get to know him

We all want to know things about the guy we like, especially if we want to date him. But, sometimes, the questions to ask a guy are embarrassing. They can be embarrassing for him or us.

It can be awkward to ask a guy something personal or sexual, but when you need the answer, you need the answer. Sometimes you just have to ask a guy those awkward and embarrassing questions.

Although it can feel silly at the moment, there is an art and necessity to asking awkward questions. You need to be sensitive with your queries and nonjudgmental when it comes to the answers.

The answers could give you so much insight into him, your future, and even how comfortable you are with him. Give this list of awkward questions a try, and work your way down the list.

1. What are you most scared of?
If you are dating someone, this is an essential yet awkward question to ask a guy. Whether his answer is the dark or losing you, it is good to know where his head is for the sake of your future together or separately.

2. What makes you feel insecure?
This might seem like something that is none of your business. You surely don’t want to share your insecurities with him, but you know how important it is.

By sharing this information, you know exactly what topics to keep positive or to avoid. If he is insecure about his abilities sexually, jealousy, his work, or he just feels weird about his hairline, knowing this can help him gain confidence. [Read: 13 signs of insecurity in a man that can ruin a perfect relationship]

3. Have you ever cheated on someone?
This is totally something you deserve to know the answer to when you are seeing a guy. Sure, he might lie, but it is a good sign if he is honest and explains his situation and what he learned from it.

The phrase, ‘once a cheater, always a cheater,’ holds some water, so you deserve to know what you’re dealing with.

4. What have you learned from your past relationships?
This is always an awkward question for a guy if it is about an ex, but it is also vital. You want to make sure he is over his ex. You also want to make sure he has learned from past relationships. If he goes on and on about how crazy his ex was, odds are he blames her for things he did wrong and will do the same to you.

5. Have you been tested for STIs?
If you are planning on having sex, you have to talk about it. It isn’t about trust or intrusiveness but about protecting yourself.

In the same way, you need to discuss birth control and not just assume the other person has it taken care of. This is a vital topic to talk about with a guy, no matter how awkward or embarrassing. [Read: How to have safe sex in every way it is possible to]

6. What are you sexual fantasies?
Sex isn’t all about touching and kissing. When it comes to sex, the golden rule is that you shouldn’t be having it if you can’t talk about it. That goes for safe sex and sexual desires.

It can be weird to share something that feels so intimate and personal, but you want to please each other when dating a guy. Offering up this vulnerable topic can bring you a lot closer and make your sex off the charts amazing. [Read: The top 50 kinky sex ideas worth trying at least once in your lifetime]

7. How experienced are you?
You don’t need to ask how many partners he has had because it is over the line. But an embarrassing question you can ask a guy is how far he has gone.

Whether he is a virgin, has been pretty wild, or what have you is crucial. You want to know what he is comfortable with and share your comfort level.

8. Do you regret anything?
Whether he lives with regret or regrets something minor, it is essential either way. It is awkward to ask a guy a question like this because he probably doesn’t want to admit to a mistake, but you know you have a keeper if he can. When a guy can own up to his shit, he is not full of ego.

9. What do you want between us?
Don’t be embarrassed and ask a guy about getting married, but you can and should ask what he wants, no matter how awkward. The ‘what are we?’ talk is always uncomfortable, but it is necessary to clarify your situation. [Read: How to get an answer to the ‘what are we?’ question]

10. What makes you feel the most awkward?
Is he awkward in social situations? Does he hate interviews or first dates? What makes him feel uncomfortable? Asking this can help him open up to you.

Just be prepared to answer yourself. Maybe you can help each other break down those walls.

11. What is the first thing you noticed about me?
This is always an awkward question to ask a guy because his answer could come out of left field. But, if you want to know what he first saw when he looked at you, ask. It could be very eye-opening. Was it love at first sight? Did he see a stain on your shirt? Or was he entranced by your beauty?

12. What is your most embarrassing moment?
This is a great first-date question to ask a guy. Yes, it is embarrassing, but that is the whole point. Showing that you and he can be humble and honest is a great way to know each other better.

13. When was the last time you cried and why?
Society has imprinted the idea into men that boys don’t cry. Of course, that’s rubbish! But what does he have to say about it? Did he cry while watching a movie? Or was it when something bad happened in his life?

14. What are your biggest goals in life, personal and professional?
This awkward question to ask a guy can help you take a peek into his dreams and desires. Does he want to be a millionare? Is he working towards it? Is he looking for true love? Is he content with his life? And most importantly, is he grateful for what he has already?

15. What is something you want to know but are embarrased to ask me?
Find out what he wants to know about you. Let him be the awkward and embarrassing one for a change.