20 Funny Questions to Ask Your Boyfriend

By on December 7, 2013

Want to spice up the conversation with your man? Or perhaps you’re just looking to find out the goofier side of your boyfriend? Either way, these 20 funny questions to ask your boyfriend will have the two of you holding your sides!

1. What fictional character would you be?


Obviously a hilarious question- who knows what he will come up with! Plus the mental image of your boyfriend wearing the costume of his favored fictional character is sure to bring a laugh or two.

2. What fruit would you be?


This question is just plain out ridiculous- and funny! Does your boyfriend dream of being an apple hanging from a tree, or would he rather be an exotic mango from a deserted island? There’s really no telling what he’ll come up with.

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


Whether he slipped on a banana peel or walked out of the bathroom with toilet paper hanging out of his jeans, his most embarrassing moment is undoubtedly going to make you giggle endlessly.

4. What was your worst date?


We’ve all heard of dating horror stories. Does your boyfriend have a hilarious story about a date he wishes he could forget?

5. If you named a drink after yourself, what would it be?


This question really gives your man the opportunity to be as funny and creative as his heart desires.

6. What qualities of mine do you dislike?

bad habits2

We never want to hear the negative parts about ourselves. But when it’s coming from an honest boyfriend, the results can be pretty funny. Just remember that this is a funny question and is nothing to take too seriously. Remain light-hearted!

7. What is your deepest darkest secret that nobody else knows?

deep secret

This could end up being a really funny or serious answer. But either way, you’ll find out something about your man that absolutely no one else knows. Now that is trust!

8. In one word, how did you feel about me when you first saw me?

Side swept bangs_48

Sometimes you’ll get a funny answer like ‘Oh, I thought you were a total nerd!’ in which case you’ll both giggle about how dorky you were. On the other hand, this could end up an incredibly romantic answer that sends the two of you closer to tying the knot.

9. Do you like my friends?


For some reason, boyfriends usually don’t like their girlfriends friends. Therefore, this question might promote your boyfriend to make a few jokes about your friends (that you can totally relate to!).

10. If you were taken by aliens, what would you do?


The question alone is pretty funny. But your boyfriend turning into a warrior hero fending off the alien species may be even funnier.

11. What would you do if I accidentally farted?


These things just happen. But it’s always a good thing to know how he will react before the actual embarrassing incident happens.

12. Do you secretly enjoy chick flicks?


You never know- your man could have a feminine side, and his favorite movie might be the Notebook.

13. Have you ever worn makeup?


Whether it was eyeliner for a rock concert or something his guy pals did while he was fast asleep, admitting that he’s worn makeup is sure to get some laughs.

14. Is there anything silly you’re afraid of?


You might be shocked with the answer you get- is your rough and tough boyfriend secretly afraid of itsy bitsy spiders? Or is your black belt boyfriend terribly afraid of ladybugs?

15. Would you ever dance ballet with me?


Seeing your boyfriend in a pair of tights is an obvious win for you- you just have to find out whether or not he’s up for the challenge.

16. What is something you’re secretly insecure about?


With this question you have a great chance at some easy compliments. He doesn’t like his nose? No problem. Tell him how incredibly cute and attractive he is, and watch his ego grow.

17. What’s the wildest thing you’ve ever done?

extreme sports

Get ready for some seriously crazy- and probably very intriguing answers. Your boyfriend might be a bit wilder than you ever imagined.

18. If you were a woman for a day, what would you do?


This question always sparks up some hilarious answers. Who knows what incredibly weird or funny things he will come up with!

19. What is the funniest dream you have had?


Dreams are completely random sometimes, and finding out what your partner’s brain has come up with during slumber is sure to bring a few laughs. Perhaps he was walking through the streets completely nude?

20. Would you rather be incredibly short or incredibly tall?


This question is just plain fun, because either way you’ll receive an answer filled with explanations. Maybe he’d prefer to be small to hide in tiny crevices, or so tall that he could smash buildings beneath his feet.


Leave a Reply

Your email address will not be published. Required fields are marked *