So you’re looking for some very awkward questions to ask a woman? Well you have come to the right place.

In this article you will find a compilation of all the questions that girls find very uncomfortable . Some of the questions have to be used with care as they can be quite annoying, but we have included them in the list anyway.

 These uncomfortable questions can be asked of any girl even if she is not in a relationship. They are questions to have a good time with a friend, with your girlfriend or with a girl you like.

Broadly speaking, an uncomfortable question would be any question that talks about a woman’s insecurities, such as appearance, gender and weight. 

But be careful!. Any question that seems awkward to a girl could also be awkward to a guy.

Table of Contents

  • 1 50 awkward questions to ask a woman
    • 1.1 20 uncomfortable general questions for women
    • 1.2 30 awkward questions related to sex to ask a girl

50 awkward questions to ask a woman

20 awkward general questions for women

1- How much do you weigh?

One of the most uncomfortable questions you can ask a woman and especially if she is somewhat out of her ideal weight.

2- What is the most embarrassing experience you’ve ever had?

With this question you will make her think and it will also help you to get to know that woman a little more about the situations that make her ashamed.

Why are you still single?

Another one of those questions that can be very uncomfortable since it may be that you are wanting to get married but your partner does not like the idea of ​​marriage or you are an independent person who flees from commitment.

Have you ever been addicted to drugs?

The question of drugs and addictions is always very uncomfortable. Will he tell the truth?

Have you ever stolen?

Another uncomfortable question that depending on the way that woman is, it may be that by pretending she does not dare to admit it.

How much do you currently earn?

Many women find it uncomfortable to admit how much money they earn.

If you could kill someone without anyone knowing, would you?

A question that will undoubtedly make the woman think that you ask her.

How long have you been without showering? 

Personal hygiene is something very intimate, so this question and its answer can be very uncomfortable.

How long do you think people should be in a relationship before thinking about getting married?

A question that tries to find out how that woman sees relationships.

What is the most intimate secret of your life?

This type of question may not have an answer, and that secret remains undiscovered.

How many guys have you dated so far?

An uncomfortable question to ask a woman since sometimes acknowledging that a woman has had many relationships is not well seen.

Have you ever tried to pee while standing up?

Well, this uncomfortable question will bring to your mind the image of that woman urinating standing up….

If you were ever asked to choose between love and money, what would you choose?

The eternal question of love and money…..

What do you like most about yourself?

Saying what you like about yourself can be very uncomfortable.

Have you used the internet to flirt?

Although today it is quite common to use different apps to flirt, it may be uncomfortable for that woman to recognize it.

Have you ever driven drunk?

If one thing is clear, it is that alcohol and driving should never go together. Dare you admit it?

Have you ever regretted hooking up with someone?

There can always be that person of whom we feel ashamed when remembering that you slept together and that nothing really should have happened.

Do you think our relationship will end in marriage?

An uncomfortable question because it reveals what you really think about the future of your relationship.

What is the worst thing you have done for love?

We all have unspeakable sins that we have done out of love and that under normal circumstances would never have taken place.

Have you ever been unfaithful?

30 Awkward Sex-Related Questions To Ask A Girl

  1. Is it okay if I kiss you?
  2. What is your best type of underpants?
  3. Do you usually watch porn?
  4. Does size matter that much to you?
  5. Did you enjoy sex with your ex more than with me?
  6. Which of your friends would you love to have sex with?
  7. What time of day do you enjoy sex the most? Morning, afternoon or night?
  8. Do you think you can ever have sex in the bathroom or shower?
  9. What do you prefer, an aggressive or passive sexual partner?
  10. What are your favorite sexual positions  ?
  11. Have any of your friends or family tried to sexually abuse you?
  12. What is the most romantic place you have always dreamed of having sex?
  13. What is the strangest place you would like to have sex?
  14. What would be your reaction if you were ever caught having sex?
  15. Have you ever had sex for money?
  16. Have you ever gone to a club just for the sex?
  17. Would you ever consider having sex in a movie theater?
  18. Would you ever have sex in a church?
  19. Have you had sex with another woman? Would you like it or do you like it?
  20. Would you have a threesome with me and another woman?
  21. What do you think of anal sex?
  22. Can you masturbate in a public place if I encourage you?
  23. Can you masturbate in my presence?
  24. Would you ever have sex in your workplace?
  25. How old were you when you lost your virginity?
  26. Have you ever considered phone sex?
  27. What are your sexual fantasies?
  28. Have you ever given up on one night stand in a serious relationship?
  29. Have you ever had sex with your partner thinking of someone else?
  30. Have you ever used sex toys?
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