List Of Uncomfortable Questions To Ask A Girl

Let me clear things up for you first. Why bother when no one wants to ask or be asked an uncomfortable questions? Unfortunately, the unpleasant hard-hitting questions are the only way for people to really get down to the nitty gritty of who they’re seeing and where their relationship is going.

Though asking awkward questions isn’t anyone’s favorite pastime, here’s a list of questions that will help you figure out what you’re up against and the nature of the girl you’re dating or want to date.

• Uncomfortable Questions To Ask A Girl:

1. Has anyone ever rejected you in your entire life?
2. What is this that makes you remain single?
3. Was it you or your ex-boyfriend, who decide to bring a halt to your last relationship?
4. How long did you and your ex-boyfriend last?
5. Are you on your cycle days?
6. Can you tell me the most in-depth secret about you that nobody knows?
7. How many guys before me have you tolerated dating?
8. Have you ever been attracted to another girl before in your life?
9. What do you think of homosexuality?
10. Why do you appear less pretty than you were before?
11. While you were in school, did you ever feel attracted to any of your teachers?
12. Have you ever tried online dating?
13. Which is the most embarrassing situation you have ever found yourself in?
14. What is the naughtiest thing you have ever done in your life?
15. How much time do you take before having sex with a guy?
16. Approximately, how much profit do you make in a month?
17. What is your bra size?
18. Have you ever been infected with an STD?
19. When was the last time you visited a doctor for an STD test?
20. Why do you like makeup that much?
21. Which kind of clothes are you wearing right now?
22. What is the naughtiest dare that you have ever done?
23. Is it okay if we split this bill into half?
24. What is the most frustrating thing that you’re a best friend has ever told you?
25. Would you like to try an open relationship?
26. Have you ever embarrassed yourself because of money?
27. At what age did you lose your virginity?
28. What do you think about my looks?
29. How many times have ever cheated while in a relationship?
30. Do you tolerate cheating?
31. For how long would you like to date before saying ‘yes’ to a marriage proposal?
32. Do you feel attracted to your male best friend?
33. Have you ever tried to enter into a relationship with your friend?
34. Which kind of fantasies do you have?
35. Do you love self-pleasure?
36. Do you still feel attached to your ex-boyfriend?
37. Why do you admire your friends?
38. How long do you stay in the shower and what do you do?
39. When it comes to your moods, do you have a faked friendly attitude?
40. Is there any person you like more than me?
41. Is this the right moment to kiss you?
42. In your lifetime, have you ever tried any drugs, and if so which drug?
43. Which one would you prefer money or true love?
44. Do you have one of your friends who is a gold digger?
45. How often do you take a shower?
46. Which was the most prolonged period you had to endure without taking a shower?
47. In which category of girls do you think you fall in?
48. Isn’t it hard to wear the make up all day?
49. What do you like doing while no one is watching you?
50. How would you describe your body shape?

• Unique Questions To Ask Your Girlfriend:

1. When do you feel most free?
2. When do you feel most joyful?
3. When do you feel most fulfilled?
4. What aspects of your work make you feel these ways?
5. What aspects of spending time with others make you feel these ways?
6. What aspects of spending time with me make you feel these ways?
7. Where should our next trip be?
8. What do you imagine our next house looks like?
9. Where do you really want to live?
10. What has excited you recently?
11. What does your ideal day look like?
12. What does your ideal life look like?
13. What hobby do you wish you could pursue?
14. What do you imagine our life together looks like in the future?
15. What would you do for a year if you were free to do whatever you wanted?
16. What is the best way for me to tell you that I am out of balance?
17. How are you most comfortable letting me know that you are out of balance?
18. What do you do to take care of yourself?
19. How much space/time do you need for yourself?
20. How can I support you in taking care of yourself?
21. When you are out of balance what do you need from me?
22. What does your perfect day look like?
23. How can I be more supportive of you in day-to-day life?
24. What in this relationship has been hard for you to deal with?
25. What in past relationships has been hard to deal with?
26. What has made you feel not free?
27. How have you felt fulfilled in our relationship?
28. When have you been most joyful in our relationship?
29. What would you enjoy doing more of together?
30. In the past week, what are you most grateful for in this relationship?
31. What worries you?
32. What ticks you off?
33. Are your needs being met?
34. What scares you the most?
35. What’s your favorite date that we’ve been on?

• Awkward Questions To Ask A Girl:

1. How would you describe yourself? Angel or devil?
2. What would you do if you were invisible for a day?
3. What is the weirdest nickname you ever had?
4. What is the weirdest crush you ever had?
5. What are the best and worst about being a woman?
6. What’s your favorite joke?
7. What’s the habit you hate most in a boyfriend?
8. What’s the worst thing someone has walked in on you while doing it?
9. If people could read your mind, what would they usually hear?
10. Would you rather be beautiful and dumb or ugly and clever?
11. If you could be a guy for one day, what would you do?
12. Who would you do between…?
13. Is Your Sister/Friend Single? – Awkward Especially When You’re The One Eyeing Him
14. Am I Your Type?
15. Are Those Real? – Drunken Guys Really Come Up With The Most Awkward Questions To Ask A Girl
16. What Is The Most Embarrassing Thing That Has Ever Happened To You?
17. Why Are You Single?
18. Have You Ever Done Drugs?
19. How Much Does Your Job Pay? – Boys, This Is Definitely An Awkward Question To Ask A Girl, Especially If You’ve Just Met
20. Tell Me Something You Haven’t Told Anyone Before/What’s Your Deepest Darkest Secret? – What Makes You Think I Want To Tell You?
21. How Many Partners Have You Been With?
22. Do You Want To Go Dutch?
23. Can I Kiss You? – This Is Such An Awkward Question To Ask A Girl. A Good Response Would Be “Only If I Can Punch You”
24. Is It Okay If I Sleep Over?
25. Have You Tried Peeing Standing Up?
26. Ever Been With A Woman?
27. Do You Like That? Or Other Such Questions In Bed. There Is No Right Way To Answer That And That’s What Makes It An Awkward Question To Ask A Girl
28. Why Did Your Ex And You Part Ways?
29. Are You Pmsing? – Yes, And When I’m Done, Im Going To Kill You
30. How Come You Didn’t Return My Call? Don’t Make It Embarrassing For Yourself And For Her By Asking This Awkward Question. Obviously, She Saw Your Call And Chose Not To Return It
31. Does Size Really Matter? – Especially When You Know He’s Not As *Ahem* Gifted
32. Was Sex Better With Your Ex Than With Me?
33. Do You Love Me?
34. Anything To Do With STD’s- Important No Doubt But Also An Awkward Question To Ask A Girl
35. What Do You See In Our Future?- Again, A Vital Question At Some Point But Sure To Be Awkward
36. Have You Put On Some Weight? – This Is Possibly The Most Awkward Question To Ask A Girl. Boys, If You Value Your Lives, Find A Nicer Way Of Telling Her She’s Put On Weight
37. Do You Spit Or Swallow….Gum?
38. Am I your type of guy?
39. What would you consider the most embarrassing experience you ever had?
40. Why are you still single?
41. Have ever been a drug addict?
42. Have you ever shoplifted?
43. How much do you earn presently
44. What was the craziest thing you ever did?
45. How long have you ever stayed without a shower? What did you smell like within that period?
46. How long do you think people should be in a relationship before thinking of getting married?
47. What do you consider the deepest secret in your life?
48. How many guys have you dated so far?
49. Have you ever tried peeing while standing?
50. If you are ever asked to choose between love and money, which would you choose?
51. Have you ever embarrassed yourself in a public place?
52. How old were you when you started using the internet?
53. Have you ever been guilty of drinking and driving?
54. Have you ever regretted being with someone?
55. Do you see our relationship leading to marriage?
56. What do you find most attractive about me?
57. Did you ever kiss someone you shouldn’t have even thought of kissing?

• Hot Questions To Ask A Girl:

1. What does it feel like when you orgasm?
2. What do you need to happen for your orgasm to be absolutely mind-blowing?
3. What’s one thing that’s made you feel unexpectedly good in bed?
4. What’s one thing that you hesitated to try during sex but ended up loving?
5. Are you a screamer? A moaner?
6. How did you learn to masturbate, and how old were you when you first succeeded?
7. What’s your favorite method for getting yourself off?
8. What types of props have you used during sex?
9. What’s your favorite kind of foreplay?
10. Have you ever repurposed a regular household item as a sex toy? If so, which one(s)?
11. If you had to choose, would you be a dominatrix or a submissive?
12. What’s the nastiest thing you’ve ever said to get someone off?
13. What’s the dirtiest thing you’ve ever sexted someone?
14. Do you like taking naked photos of yourself?
15. What’s your personal record for the number of times you’ve had sex in one night?
16. What’s the most daring place you’ve done it in public?
17. What sexual position makes you feel most like yourself?
18. In what position to you orgasm most reliably?
19. What’s your favorite way to get a man off?
20. What’s your favorite blowjob technique?
21. What makes you wet without fail?
22. What’s your favorite strategy for getting him to cum asap?
23. How many different ways have you orgasmed?
24. What, if anything, makes you feel vulnerable when you’re naked with someone?
25. What makes you feel comfortable when you’re naked someone?
26. What’s your favorite part of a man’s body?
27. What’s your favorite part of your own body?
28. What’s the dirtiest dream you’ve ever had?
29. Have you ever made an erotic fantasy come true?
30. If you had one day left to live, how would you want it?
31. Who’s the one person in this world you wish you could fuck?
32. What’s the dirtiest thought you’ve ever had?
33. What’s the sexiest compliment you’ve ever gotten?
34. What’s the sexiest compliment you’ve ever given?
35. How do you like your pussy to be licked?
36. Do you like it rough or gentle?
37. What’s the most sexually daring thing you’ve ever done?
38. What’s the naughtiest thing you’ve ever asked someone to do to you?
39. How would you describe the taste of your own vagina?
40. What does your ideal penis look like?
41. How seriously do you take your sex life?
42. What turns you on the most about the opposite sex?
43. What is your hottest sexual memory?
44. What’s your biggest sexual fear?
45. If you could take on any fictional character’s personality in bed, who would you be?
46. What’s your favorite sex toy to play with?
47. Have you ever had sex with two different people in one night?
48. How good are you at faking an orgasm? Show me…
49. How many different people have you had great sex with?
50. What’s the one sex act you want to try before you die?

• 21 Sexually Questions To Ask A Girl:

1. What’s your favorite pair or underwear?
2. Where is your favorite spot to be kissed?
3. How do you feel about kissing in public?
4. What is one thing that gives you butterflies?
5. Would you hold my hand?
6. Would you let me hug you?
7. Would you let me kiss you?
8. Are you a snuggler?
9. Do you think about me when I’m away?
10. Have you ever tried to picture me naked?
11. What is the most exotic dream you’ve ever had?
12. What is the most exotic dream you’ve had about me?
13. What was your first impression of me?
14. Using three words, how do you feel about me?
15. If you were to give me a pet name, what would it be?
16. What are you doing later?
17. When did you first realize you liked me?
18. What is your favorite thing about when we’re together?
19. Have you been working out?
20. Can you tell me some reasons why I like you?
21. What do you expect most out of a relationship?

• Sex 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?

Have you ever used sex toys?