Awkward Questions to Ask A Girl

Asking questions plays a significant role in creating a conversation with a girl since one thing may lead to another. However, time to time you may be caught up in a dilemma on whether to ask a girl a specific question or to let it just pass. It is very normal if you have ever asked a girl question and she decided not to answer it, she just kept quiet, and you were left wondering why she did it. I am very sure it has happened to your time and again but there is a reason to that.

Some of these questions may not be really awkward you, but to a girl, it may hint at insecurity she doesn’t want out there. Likewise, a question can be really awkward if it’s not asked at the perfect moment. You can gauge to know she will really consider it uncomfortable by the time you have spent together. If you have spent more time together, then some of these questions will be less awkward to her. Well, let’s get right to the kind questions which are embarrassing 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?

#51) If you were to change a part of your body which part would it be?

#52) Which is your favorite part of your body?

#53) Which part of the man’s body do you like the most?

#54) Have you ever tried picking your nose?

#55) Which type of men makes you feel as if you are allergic to them?

#56) Can you describe the weirdest person you have ever dated?

#57) If you were given a chance to change your gender would you do it?

#58) What do you hate most about being a woman?

#59) Which habitual thing do you hate most in men?

#60) Which kind of difficulties are you experiencing right now?

#61) Have you ever felt jealous of the most beautiful friend you have?

#62) Which rule do you feel proud of breaking?

#63) If you were to write the story of your life how would you let it turn out?

#64) Which part of your life would you like to erase?

#65) Would you change your religion for me?

#66) Which is the most embarrassing thing you have ever done in front of a man?

#67) What is your love fantasy?

#68) What do you always do while you free late at night?

#69) Have ever freed yourself from your principles for a while a while?

#70) Can you fall in love with the same person who hurt you before?

#71) Have you ever lost your dream in life somewhere in the way?

#72) Can you describe me the man of your dreams?

#73) What makes you feel insecure about your body?

#74) Do you think that women look prettier or much worse in makeup?

#75) How many men have you ever dated at the same time?

#76) Which years would you like to skip in your life?

#77) Has one of your friends ever turned on you?

#78) Are you attached to monetary things?

#79) Would you date a guy because of how rich he is?

#80) Do you consider yourself as a lousy company?

#81) Which of your worst fears has ever come true?

#82) In which way do you reduce your stress?

#83) Do you always go out at night?

#84) Do you like parting?

#85) Have you ever considered yourself as a girl who cannot fit in?

#86) When are you likely to feel shy around a guy?

#87) Can you describe yourself as a nasty girl?

#88) In your collection, which is the ugliest thing which you own?

#89) What’s the most illegal thing you have ever done that could have got you arrested?

#90) What are the most remarkable things that guys do to you?

#91) Are you into politics or football?

#92) Based on the history of women drivers would you feel confident driving a car?

#93) Do you know that you are always on my mind?

#94) Can you give me a number of how many men you have slept with?

#95) On a scale of 1-10 could you rate me?

#96) Do you think that I am better than you ex-boyfriend?

#97) Which is your favorite position in sex?

#98) Have you ever thought of using your body to earn money?

#99) Can you date a guy who is older than you?

#100) Do I fit as the type to become your boyfriend?

Well, by now you have a grip on the most awkward questions that you can avoid to ask a girl on your first date. Anyway, not all the question will turn out to be awkward when they are asked at the right moment. If you feel the right time has come to ask, you can go ahead and do it. The level of awkwardness can also depend on the personality of the girl. Some of the girls out there are pretty open, and they are the kind that will feel less awkward when asked a question.