100+ Awkward questions to ask a girl!

Awkward questions to ask a girl
By Tessa Updated

Questions which genetically sound good may not be apt for every situation. Sometimes, we need to take the help of awkward questions to anticipate a person better. Honestly, the modern era is very upfront. People hardly differentiate between genders. Sex, racism, gender these are no more taboo in a society. These days, it is quite easy to think of awkward questions to ask a girl.

An awkward question has an excessive polished surface but can be very uneven at its core. There would always be some issues like sex, weight, age etc. that bother a girl. So, these are automatically considered as awkward.

A List of Awkward Questions to Ask a Girl

Here, we have provided 100+ awkward questions to ask a girl. We have made it suitable keeping in mind a variety of occasions. You can comfortably ask these to a lady. But, always remember one thing, that questions which are awkward to a girl would always be awkward to a guy as well.

General Awkward Questions to Ask a Girl

  1. Do you like me?
  2. Do you trust me?
  3. Are you single?
  4. How old are you?
  5. Do you weigh yourself frequently?
  6. Which is the most embarrassing moment you have ever had?
  7. Have you ever taken drugs?
  8. What is your current salary?
  9. How much crazy are you? Have you ever done something which you could have never thought of?
  10. Why you did not get the promotion; you work so hard?
  1. Are you on your periods?
  2. Would you like to have a one night stand with me?
  3. How long do you think one should be in a relationship before thinking of getting married?
  4. What is the one thing which nobody knows about you?
  5. How many guys have you dated so far?
  6. Is there anything you avoid to talk always?
  7. Have you ever tried to pee while standing?
  8. What is more important to you, financial stability or love?
  9. Do you drink?
  10. Have you ever discovered the Dark Web?
  11. Do you smoke?
  12. Why did you leave that job?
  13. Have faced a charge of drink and drive?
  14. Have you ever rejected anyone?
  15. Do you have any weird breakup experience?
  16. Why is your face looking so dull?
  17. Can we hang out together just for fun?
  18. Did you kiss anyone before?
  19. What is the thought comes to your mind while you kiss?
  20. Can I kiss you?
  21. Do you believe in bisexuality?
  22. Has anybody had ever hit on you?
  23. Did you have a crush on your teacher? When did that happen?
  24. Do you love to party a lot?
  25. Have you ever fantasized anyone in your dream?
  26. Would you ever do something only for money?
  27. Did you ever experience anything weird in a night bar?
  28. Have you ever been approached by any girl?
  29. Did you have any misconception related to your puberty?
  30. Has anyone cheated on you in a relationship?
  31. What is the first weird thing you do in the morning?
  32. Have you ever shown a fake attitude to anyone?
  33. What do you think of an open relationship?
  34. Would you like to split the bill with me?
  35. Would you consider me hot and handsome?
  36. What is your worst flirtatious experience?
  37. How far can you go with your online date?
  38. What is the most insane challenge you have ever accepted in a Truth and Dare game?
  39. What is the hilarious naughty joke you have ever heard?
  40. Would you ever picture me having sex with your best friend?
  41. What is the most expensive piece of lingerie you have ever bought?
  42. Do you like hairy chest?
  43. What is the unusual thing you do to relax?
  44. Before giving consent for marriage, what would you like to experience with your partner?
  45. What is the one thing you want to flush out from your life?
  46. What can make you wild anytime?
  47. Would you call yourself a hardcore feminist?
  48. Men and women are equal – are they truly?
  49. Which is the one food you cannot live without?
  50. Would you ever share the last piece of chicken burger with me?
  51. If I ever tell you to come without makeup, would you do that?
  52. What is the worst pickup line you have ever heard of?
  53. Have you ever expensed your last bit of savings to buy a luxury cosmetics?
  54. How would you react if a stranger suddenly kisses you?
  55. What are you wearing right now?
  56. What is the weirdest thing you have done in a lone night?
  57. Hug or kiss, which one do you find romantic?
  58. Have you ever done anything crazy with your best friend?

Sex-Related Awkward Questions to Ask a Girl

  1. Have you ever slept with a guy?
  2. Can we be friends? Though sex is also on my mind!
  3. Did you ever have sex before?
  4. Are you a virgin?
  5. What is your wildest fantasy?
  6. Is morning boner good or irritating? – think of a guy’s perspective.
  7. Can you send me a sexy picture of you?
  8. Would you like to do anal sex with me?
  9. If I give you a dare that you have to masturbate in public, would you do that?
  10. What is the first sex toy you used?
  11. Have you ever had sex without a condom?
  12. Have you ever pictured me naked?
  13. What do you think of BDSM?
  14. How did you react when you first saw your breasts?
  15. Have you ever experienced any weird sexual behavior?
  16. Have you ever had sex in your workplace?
  17. When did you lose your virginity?
  18. Have you ever had sex with a younger man than you?
  19. Were you asked for sex by any of your seniors or bosses?
  20. Do you scream during sex?
  1. Has any of your past dates turned into something wild?
  2. Which is the weirdest place you would like to have sex?
  3. How would you react if your parents find you in an uncomfortable position with your
  4. boyfriend?
  5. Have you ever been caught while watching porn at home?
  6. Would you ever have sex in a hotel?
  7. What is the wildest thing you can do with me?
  8. What excites you during sex?
  9. Does size matter to you while having sex?
  10. Have you ever had ‘Friends with Benefits’ moments with anyone?
  11. When do you enjoy sex the most?
  12. Have you ever read Kamasutra?
  13. Can we take a shower together?
  14. What do you like while having sex: candlelight or music or both?
  15. Why did you have an abortion?
  16. Which is the thing you condemn the most?
  17. What is your bra size?
  18. Which is your favorite lingerie?

Awkward questions can go to any level, and honestly, there is no such limit. A guy always needs to draw the borderline himself. We have compiled some of the best awkward questions to ask a girl. These questions have blunt edges and you can modify them anytime according to a particular situation. So, now when you have the list, are you ready to hop in for an adventurous date with your dream girl?


  • Do not make the situation uncomfortable with an unnecessary pause. It might give a bad signal to the girl.
  • Be relaxed while asking.
  • And lastly always remember that there is nothing like taboo topics. The only thing that matters is whether you are maintaining a decency level or not.