So you need some very awkward questions to ask a girl? Yes, you get them in the right place. This article has a compilation of all the questions girls find very awkward. Some the questions might be quite annoying, but they were still included on the list anyway. Specifically, these are simple questions a guy can ask a girl, and not necessarily for people who are already in a relationship. On a general note, any question that bothers on the girl's insecurities, such as looks, sex, weight, will always appear awkward. And don't forget to prepare yourself. Any question that appears awkward for a girl could also be awkward for a guy.

50 Awkward Questions to Ask a Girl


20 General Awkward Questions to Ask a Girl

  1. Am I your type of guy?

  2. What would you consider the most embarrassing experience you ever had?

  3. Why are you still single?

  4. Have ever been a drug addict?

  5. Have you ever shoplifted?

  6. How much do you earn presently

  7. What was the craziest thing you ever did?

  8. How long have you ever stayed without a shower? What did you smell like within that period?

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

  10. What do you consider the deepest secret in your life?

  11. How many guys have you dated so far?

  12. Have you ever tried peeing while standing?

  13. If you are ever asked to choose between love and money, which would you choose?

  14. Have you ever embarrassed yourself in a public place?

  15. How old were you when you started using the internet?

  16. Have you ever been guilty of drinking and driving?

  17. Have you ever regretted being with someone?

  18. Do you see our relationship leading to marriage?

  19. What do you find most attractive about me?

  20. Did you ever kiss someone you shouldn't have even thought of kissing?


30 Sex Related Awkward Questions to Ask a Girl

  1. Is it OK if I kiss you?

  2. What is your best kind of underpants?

  3. Have you dated a fellow girl before?

  4. Does size matter to you that much?

  5. Did enjoy sex with your ex better than you do with me?

  6. Which of your male friends would you love to have sex with?

  7. What time of the day do you enjoy sex most? Morning, afternoon, or night?

  8. Do you think you can ever have sex in the bath or shower?

  9. Which do you prefer, an aggressive or passive sex partner?

  10. What are your favorite sex positions?

  11. Has any of your friends or relatives ever tried to abuse you sexually?

  12. What is the most romantic location you have always dreamt of having sex?

  13. What is the weirdest spot you would love to have sex in?

  14. What would be your reaction if you ever get 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 theatre?

  18. Would you consider having sex outside a movie theatre?

  19. Would you ever have sex in a church?

  20. Can you go for anal sex?

  21. Can you masturbate in a public place if I dared you to?

  22. Can you masturbate in my presence?

  23. Would you ever have sex in your place of work?

  24. How old were you when you lost your virginity?

  25. Have ever considered phone sex?

  26. What are your sexual fantasies?

  27. Have you ever given in for a one night stand while in a serious relationship?

  28. Have ever called your mate someone else's name during sex?

  29. Have you ever engaged in group sex?

  30. Have you ever used sex toys?


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