150+ Random Questions To Ask A Guy


Good communication is one major ingredients for a happy and successful relationship. A relationship starts to deteriorate when there is a break in communication. Communication  also includes asking questions especially about each other, because the more you understand each other the better the relationship becomes. Despite the fact that you are deeply in love with your boyfriend, there are times when conversation is dry and you may seem to not have anything to talk about, making the atmosphere boring, this is actually the perfect time to take advantage of and ask him some random but crucial questions. Incase you don’t know what to ask, here is a list of some of the random questions to ask a guy.

Random Questions To Ask A Guy

Random Questions to Ask a Guy

What are your regrets in life?

When was the last time you cried?

Describe your relationship with your mother and sister?

Do you sing while taking bath?

Do you snore while sleeping?

Have you ever taken advantage of anyone?

Do you like to clean your room?

If you could live anywhere in the world, where would it be?

Into which personality’s shoes would you like to step for a day?

What 5 words would a close friend use to describe you?

Do you believe in love at first sight?

What is your most treasured possession and why?

What is your favorite month of the year?

Which is the place/country that you want to visit?

What are your hobbies or interest?

Do you like reading? Which is your favorite book?

Do you have a pet name? How did you get it?

Who all are there in your family?

Who is your inspiration?

Which is the best holiday you ever had?

How much do you love me?

Do you dream of a future with me?

Would you accept me if I cheat on you?

Do you approve of working married women?

What is the thing that you like most about me?

Which is your ideal honeymoon destination?

Did you ever have a crush on your teacher or some other woman?

Would you talk to me at night if you are feeling dead sleepy?

Are you a virgin? If not, when did you lose your virginity?

Who do you find most beautiful among my friends?

What was your first impression of me?
Do you watch porn?
How would you react if you found your girlfriend or wife was into porn?
Are there any fears you have that you would like to get over?

Do you find yourself prejudiced or biased in any area?

Tell me five of your pet peeves?

If you could have sex with any three people you chose, who would they be?

When you meet someone of the opposite sex, what do you first notice about them?

Which are the parts of their body that you notice?

Have you ever dated two girls at once without either of them being the wiser about it?

Have you ever been arrested or charged with a crime?

Have you ever used being drunk as an excuse for doing or saying something?

Who is your role model?

What do you do in your free time?

Do you like children?

How would you deal with a difficult mother-in-law?

Tell me about your strengths and weaknesses?

What are your career aspirations and dreams?

What’s the hardest thing you’ve ever done?

What is your idea of a perfect Valentine’s Day?

If I ask you to dedicate a song to me, what would it be?

What would you do if I die?

What are the things that you can do to cheer me up?

Do you believe in the seven births companionship concept?

What is your favorite dish?

Who is your favorite actress?

What’s your favorite movie and why?

Would you rather spend a day in the woods or at the beach? Why?

Tell me about a sporting event you’ll never forget

If you could have any superpower, what would it be?

Which is the one job in the world that you would love to do?

If you were an animal in the wild, what would you be?

What is the most embarrassing moment of your life?

Who was your first girlfriend?

Why did you break up with her?

Which is your dream car?

Do you like pets?

Will you like to keep any at home?

If you win a lottery of $1000, what will you do with it?

Are there any causes you strongly believe in?

If you won a million dollars in a lottery, what would you do with it?

If you knew you had only 2 weeks to live and death was imminent what ae the regrets you would have?

Why haven’t you done anything about those regrets?

How would you spend those two weeks?

Is there someone from the past you really miss and would like to locate?

Who was your first love?

If you could take a year off and go travelling, where would it be?

Which sports do you play or watch?

Which is your favorite Comic book character?

What do you like about him/her?

If you could relive the last five years of your life, what would you change?