35 Awkward Questions Guys Secretly Want To Ask Girls

If you have something in your mind, then you shouldn’t hold it inside. You must share it with your girl. It might seem awkward to ask, but if the thought has crossed your mind, then you should ask these awkward questions. She might get angry at you, but at the end, you won’t have any doubt in mind. Trust and honesty go hand in hand, so always be honest in your relationship because a simple lie can ruin your relationship. Girls are insecure about their looks, weight, and height, so if you have any question related to these issues, then it will be quite awkward for her to answer your questions. So, the responsibility is on you to make her feel comfortable by framing the questions in the nicest way possible. Hey, it’s not that difficult. Trust me, you just go through the questions that we have suggested below and you will sail through all the awkwardness.

It is very important that the girl you like feels comfortable with you and is in a good mood. If you sense that she is not to the best of her mood then drop the idea of asking her all these awkward questions. Rather, compliment her about her looks and personality and how she has made your life a beautiful one. The girls would always love to know whether she could make any significant difference in your life or not. Once she is all smiles you can ask your girlfriend the awkward questions that you thought of asking her in the first place.

Your curiosity is about to end because all the questions that were in your mind are going to come up in the open. Though a clear communication is always welcomed, still when you are asking some personal questions it might open a can of worms. So, be prepared to handle the situation.

1. Why have you been single for so long?

It might come across as a harmless question, but for her, it is an awkward question to answer. You need to be prepared to explain the question to the girl you like. You are just curious that why she is still single, right? If you ask her casually, she will feel much more comfortable in answering the question that you have asked her.

2. Are you serious about me?

This will give you a clear idea about what she thinks about you and whether there is any hope of a great future with her. She is the girl you like, but you are not sure whether she also thinks in the same line or not. So, this question will provide you a lucid perspective of your relationship. If she hasn’t given it a thought then she might evade the question by answering vaguely, but you can prod her a little more to know the truth.

3. When do you want to get married?

This is a tricky question, but if she has evaded your previous question, then you can definitely ask her this question. Everybody has a marriage plan set in their mind, so this time around you can expect a definite answer from your girlfriend.

4. Do you think splitting the bill is a nice idea?

It’s a dreadful question to ask your girlfriend when the bill is on the table. So, ask this question beforehand. Some girls love the idea of splitting the bill, whereas there are some who thinks that her guy should pay the bill when they are out. It is better to know the girl you like prior to the dinner date so that you can avoid any kind of embarrassing situation regarding the bill. It won’t make you sound cheap if you ask your girlfriend this question.

5. Do you find me hot?

When it comes to looks, then men and women are equally insecure. But, a guy might feel a bit embarrassed to ask this question to her girlfriend. You shouldn’t feel embarrassed at all. Go and ask your girl whether she find you hot or not.

You know that there some forbidden questions that you must never ask the girl you like, but you cannot hold your thoughts back. It is lingering in your mind for long. What to do? You can hold it back and have all kinds of doubts and skepticism or you can get rid of the inhibitions and ask her directly. The choice is yours. You just have to keep in mind that when you are touching on the taboo topics you should do it gracefully.

Okay, so now you want to get a bit up, close and personal with her, but prior to that, you want to know her preferences. So, here is a list of questions that will let you know what she prefers.

6. Do you want a little bondage while getting intimate or do you want to go all out?

It can be quite embarrassing for both of you, but if you want to know what your girl wants, you have to come straight. She might feel a bit shy, but if you prod her a bit, then you will surely get an answer.

7. Do you like boxers or briefs?

It is one of the common things to have, but asking this question can be quite awkward. But, it is fun to know whether you need to change or stay put with what you have.

8. At what time of the day will you love to get intimate?

It is quite an awkward question to ask your girlfriend but if you want to make her happy then you should know her preferences. It will be easier for you to approach her.

9. Do you have any kind of fantasies?

When you have already asked the other questions, it might not be that awkward for you to ask. But, if it is important for you to know about her fantasies while getting intimate, then don’t hesitate to ask her this awkward question.

10. Will you mind if I start getting intimate on the phone?

Some girls love the idea of getting naughty while talking to their boyfriend over the phone. So, in order to find out whether the girl you like loves it or not, you will have to pop this awkward question to her.

We sometimes hold back our thoughts thinking that our partner might get offended by our questions. But, that is not right for any relationship. Our casual thoughts sometimes turn into evil thoughts and make our relationship sour. All this happens because we held back our thoughts and didn’t share it with the person whom we liked. When you are asking questions, your doubts are getting cleared. In any relationship, there is no room for doubts. If doubts and lies take over, then your relationship won’t stand the test of time.

If you want to know her more closely, then you will have to make an effort to know her behavior pattern, what she likes and what she hates the most. Once you are aware of everything she did in the past you will be able to accept the girl you like with open arms.

11. Have you ever been into drugs?

There are times when peer pressure makes us do things that we regret later. She might have gone through the same situation and been into drugs for a while. So, make her understand why you are asking this question and she will confide in you without hesitating.

12. Have you dated any guy before me?

As a guy, it is very important that you know whether you are the first man in her life or she has dated before. If she likes you she will be honest with you.

13. What is your present salary?

Asking about how much she earns can be a risky affair, but if you can put it nicely, then it won’t hurt.

14. Have you ever felt embarrassed in public place?

There are times when we do something in a public place thinking that nobody is watching us and then all of a sudden we realize that every eye was on us. You can ask her this question just to know whether she also has faced this kind of situation or not?

15. Have you ever been booked for DUI?

Most of us think that we can get away with drinking and driving, but not always luck is on our side. If she drinks, then it can be a possibility that she is booked for DUI. Clear your doubts by asking her this question.

Not always, we can ask awkward questions to our girlfriends because we are scared of hurting her. But, there are some awkward questions that are important to ask. Without knowing the answers to all these awkward questions your relationship might be incomplete.

Don’t think she will judge you while you are asking her these awkward questions. She won’t. She might get surprised when you start off, but gradually she will understand and will answer all your queries without hesitating.

16. Have you ever worn a dress inside out?

When we are in a hurry, we barely look at what we are wearing, so in a hurry, a t-shirt can be worn inside out and when we are in the public place we realize what we have done when everybody stares at us. Ask the girl you like, whether the same thing had happened to her as well?

17. Would you like to get intimate with me tonight?

You've been going out for a long time and now you want to know whether she would love some kind of intimacy or not. You never know, she might be waiting for you to ask her this question.

18. Which body parts of mine do you like the most?

If you are not sure what she likes about you, then the best thing to do is ask her.

19. Am I better than your ex?

If you know that she had a boyfriend before she started dating you and you are insecure about him, then you can pop the question in front of her and let her know about your feelings.

20. Have you ever regretted the thought of being with someone?

We get into a relationship very quickly and then we realize that the person is not best suited for me. Then we regret it, so if she also had a past you will get to know about it.

There is some social stigma attached to topics like money, intimacy, looks, and various other things like these. Be it a girl or a boy, it is an unsaid rule that we should not ask the questions that can make the other awkward. But, if we stop asking these questions, then how will we know each other better? Right, so don’t hesitate.

Your approach should be correct and everything else will fall into place.

21. Do you want to pursue your career after marriage?

You will find girls who want to take care of their family after marriage and doesn’t want to pursue their career and then there are some who are fiercely independent and are very much focused on their career. Asking this question will help you know your girl better.

22. How long do you think one should wait before planning a family?

It always differs from one person to the other. So, if you are serious about her then it is better to have an idea about what she thinks about this topic.

23. Would you like to be a full-time, hands-on mother or a working mother?

The decision should be hers. Ask this question to your girlfriend, so that she gets enough time to decide what she actually wants.

24. Have you ever felt jealous of the other girl’s curve?

The girl you like might not be fully satisfied with the body type she possesses, so asking this question will help you understand her insecurities.

25. Would you like it if I kissed you in public?

She might get offended if you do it, so asking it beforehand will save you from her slap across your cheek.

Misunderstanding is one of the major reasons for relationships going sour and this misunderstanding crop up when we stop asking questions, thinking that it might be awkward for her to answer. It is better to land up in an awkward situation rather than allowing your relationship to slip into a coma.

Flirting always works. Once you know that the girl you like is yours, you stop flirting with her. But, that should not be the case.

26. Where do you enjoy being stroked the most?

If you want to know whether you are doing it right, then ask her. It’s simple though it can be awkward for you to pop the question to her.

27. Are you hiding anything from me?

All of us have some secrets in our life that we share only with those who are really very close to us. If she answers your question, then you can consider yourself a one of the most important person in her life.

28. Whom do you find attractive: older men or younger men?

Some girls love to hang out with young men, ask her the question to know what she thinks about it.

29. Have you ever cheated on someone?

It is pretty awkward to ask this question to the girl you like. She will think that you might judge her and avoid answering this question. But make her realize that you won’t judge her and she will bare her heart out to you.

30. What attracts you the most in men?

It can be his sense of humor or the smell or the features. You will only be able to know when you ask her this question.

Awkward questions are not always bad. They will also give you enough fodder to laugh at. It will help you understand the girl you like in a better light. Just make sure that you don’t judge her after listening to all her answers.

These awkward questions will help you in steering your relationship to an interesting level altogether. Try it out at least one.

31. Do you like to sleep with your clothes on or without it?

If you answer this question first, then she will feel comfortable in replying you. Otherwise, it will be embarrassing for her.

32. What is the first thing that you notice in a man?

You will be pleasantly surprised to know the answer to this question because some girls like the shoes, some like the smile whereas some just can't resist the perfume that a guy wears.

33. Would you get intimate with any celebrity?

She might have a huge crush on some celebrity, so you can ask her how close she would go with that celebrity.

34. Have you ever got caught for getting intimate in public?

If you feel that your girl won’t be able to handle these types of questions, then the best way to make her feel comfortable is by answering the question first.

35. What do you think about the same gender relationships?

This will help you know about how and what she feels about the issue.

You can ask any question you feel like, but the most important thing is to frame it correctly. She should not feel like you are asking all these awkward questions to make her feel uncomfortable. Never ever judge her for her honest replies. If you can take her honest answers, then only ask your girlfriend these awkward questions.