104 Best Awkward Questions To Ask Your Girlfriend And Friends

Looking for some awkward questions that you can ask your friends, girlfriend or whoever you want to ask.

Then you are in the right place. Want to know some embarrassing story of your friend, or want to make them uncomfortable on purpose.

Below I have shared the best awkward questions that will make others uncomfortable when you ask them.

Awkward Questions That No One Wants To Answer

Awkward Questions

There is a blue house, a red house, a green house, and a white house. If the blue house is in the north, the green house on the east and the red house on the west, where does the white house located?

Imagine you are in a drowning boat circled by sharks. How would you survive?

If a cop, a marine, a soldier, and a seal get into a gunfight, who is guaranteed not to get shot?

Joy’s father is john. Then john is the ——– of Joy’s father.

How many birthdays does an average person have?

What do cows drink?

What’s long, hard and has cum in it?

What’s goes in hard and comes out soft and wet and don’t mind you blow me?

Whats goes in dry and comes out wet, the longer it’s in, the stronger it gets?

What you can see in water but doesn’t get wet?

Have you ever been in love?

Have you ever lived with someone you don’t know?

How long did your relationship last?

What matters to you most in a relationship?

What are your goals for dating?

Do you love me?

Have you been married before?

Do you think about marrying me?

What kind of birth control do you take or prefer?

Have you ever had an STD or disease?

Do you feel like you can talk to me about making out/sex?

What was your age when you had your first sexual intercourse?

Do you like watching pornography?

The worst crime you have committed?

For a million dollars, would you exchange your partner?

What is the worst thing you searched for on Google?

How often do you shake your little brother?

Does size matter?

Have you ever had making out/sex in the workplace?

How much do you earn?

What is the greatest rejection you have had in love and life?

Do you masturbate for a week?

Have you ever fantasized about a teacher?

What’s your age when you started masturbating?

Have you ever stolen money?

Do you like to drink alcohol?

What was the age when you had your first drink?

What was the last search on facebook?

Have you ever watch pornography with your friends?

What’s the funniest thing to ever happen to you during sexual intercourse?

Have you ever laughed in the worst situation?

Have you ever got caught while watching porno?

Would You Rather…Eat Bugs for life OR Kiss somebody 24/7

For man, is it legal to marry his widow’s sister?

How many times can you take Five from 25?

What do you put in a toaster?

What colour is a mirror?

What comes once a year twice a week?

What has the most embarrassing thing happened to you?

What are your three weaknesses?

How many seconds are in a year?

A Woman shot Her Husband Drowned Him & Hung Him Then They Went To A Restaurant For Dinner 5 Minutes Later, How Is That Possible.

There was a plane crash, every single person died, but two people survived. How is this possible?

If a frog is dead in the middle exactly in the middle of the pond and he jumps three spaces to the north where does he land?

Why don’t polar bears eat penguins?

A man condemned to death was given a choice. He was to speak a sentence and if it was true, he would be hung, and if it were false, he would be shot. He said a sentence and lived. How?

Which hand do you stir tea?

How do you like to get fucked?

What is the most explicit sexual act you have performed or would perform?

How many women have you fucked in one day?

Who was your divorce lawyer?

Your place or mine?

Are there any more at home like you?

Want to make a porno? We don’t have to tape it.

What can I do to get you to sleep with me?

Can you give me an assignment for your body?

Will you marry me for just one night?

Have you ever played leap frog naked?

Do you believe in free love?

Do you sleep naked?

Awkward questions to Ask A Guy

Awkward questions to Ask A Guy

What do you hate most about yourself?

Did you ever have a crush on your teachers?

Have you ever been arrested?

Do you lie often?

Are you ever jealous of me?

Do you think my friends are hot?

Do your socks match your underclothes?

Do you pray?

What was the most unfortunate date you have been on?

Who was your hottest girlfriend?

What is the one thing you are most embarrassed about doing to a friend?

Are you interested in a commitment?

Are you comfortable with your current job?

Have you ever worn lingerie?

Have you ever been busted doing something unusual for a guy to do?

Have you ever wanted to sleep with a movie celebrity?

Have you ever cheated on an exam? How much did you score then?

What is the most horrible and awful thing you have ever done? Did you regret doing it?

When was the last time you stole something from a close friend or family member?

Did you ever get yourself fined for peeing in a public place?

Did you ever spy on someone? Why did you do it?

Have you ever gone for a week without taking bath or brushing your teeth?

Have you ever imagined you being a woman?

What attracts you to a girl and why?

Is there a substitute or complimentary for sex?

At what age did you lose your virginity?

When was your first time kissing a girl? Did you enjoy it?

Did you wet the bed as a kid?

Which part of your body would you love to be touched and why?

What is the best method to deal with a cheating partner?

Have you ever shoplifted?

Have you ever got attracted to a girl not for her looks but for her money?

Do you still stay in touch with your ex-girlfriends?

Would you render your “services” to a girl if she was to offer you some money?

I hope you enjoy these awkward questions.

Ask these questions to your friend and make them uncomfortable or share these questions with your girlfriend.

Let me know below which question you like the most and share your awkward questions below.

Also Read-

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