Random Questions to Ask Your Boyfriend

Every now and then in a relationship, there comes an opportunity that you can ask your guy anything. Maybe he’s really drunk, or maybe you’ve been having a deep heart to heart and both been telling each other all your secrets. Well in this situation it’s prudent to take advantage of the opportunity and ask some questions that might be a bit of fun and random, but also be quite revealing and help you to learn more about him, about your relationship and about how he sees you.

Having a few questions prepared then can really help you to do this, and then when he wakes up from his hang over you can smile smugly knowing that you just outwitted him into telling you everything… (or perhaps slap him and kick him out of your house…). Read below then for some questions that can get pretty personal and give you the upper hand in the epic game of chess that is a relationship – remember, knowledge is power. Some of these can also be used for posterity, while others you can use to your advantage to be a better lover. Others will put him on the spot in a big way. Poor guy…

Random questions to ask your boyfriend

How many people have you slept with?

Have you ever found it hard to say you love me?

Which is the sexiest one of my friends?

Have you ever cheated on a previous girlfriend?

Do you have any secrets you haven’t told me?

When did you first know you loved me?

What is it about me you love?

Do you have any unfulfilled sexual fantasies? What are they?

What’s the most embarrassing thing that’s ever happened to you?

If I found out I was pregnant tomorrow what would you do?

Have I ever annoyed you?

What’s your biggest regret?

Have you ever thought about leaving me?

What’s the weirdest thing you ever masturbated too? (Be prepared for a shock…)

Have you ever been caught masturbating?

When was the best sex you ever had?

Who was your first crush?

Who’s the hottest celebrity?

What would you do if someone hurt me?

Have you ever kissed a guy?

Do you have any embarrassing nicknames?

Do you have any guilty pleasures?

Do you have a fetish?

Where do you see this relationship going?

Can you see us ever getting married?

Do you like my Mother?

Have you ever had any embarrassing diseases?

How many times do you wank during a day when I’m not around?

Do I do anything wrong when we’re having sex?

How could sex with me be better?

Do you have any insecurities?

If you could change one thing about yourself what would you change?

What’s the angriest you’ve ever been at me?

Have you ever cheated on me in your dreams?

Do you have any phobias or embarrassing fears?

Comments 1
  1. The question's are too personal. They are questions that I myself wouldn't want to answer /+ I wouldn't want to know the answer to these question's from my boyfriend!

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