60 Questions to Ask Your Boyfriend to Make Him Laugh

By: Sarah Byrne

With some men, it’s almost impossible to get them to open up. That’s why it’s a good idea to tap into his funny bone. He’ll be giving up secrets before he even realizes what you’ve done. 

Asking out-of-the-box questions is a great way to do this. So, here are 60 questions to ask your boyfriend to make him laugh. 

Table of Contents

Romantic Questions to Ask Your Boyfriend to Make Him Laugh

1. Would you eat spaghetti with me like Lady and the Tramp?
2. If I was just a head in a jar, like on Futurama, would you be sad that we couldn’t hold hands?
3. If I were turned into a snail and the only way you could be with me was to be a snail too, would you become a snail?
4. If you end up in a coma somehow, can I take selfies with you and post them on social media with romantic hashtags? #sleepyhead
5. If we woke up in a musical, would you sing a love song to me over breakfast?
6. If we were both frogs, would you share your lily pad with me?
7. Would you help me hide if you found out I was a robot that had become sentient and escaped its creator?
8. What weird family traditions do you have that you want us to continue in our relationship?
9. How would you feel if I sang a love song while staring deeply into your eyes?
10. If my name was picked for the Hunger Games, would you volunteer as tribute?

Love and laughter go hand in hand, just like you and your man. A study from the UC Davis Undergraduate Research Journal reports that sharing laughter is a good way to support a partner through a tough time. 

The study’s author, Jia Chong, says “A partner’s appropriate use of humor to cut through fear and anxiety and connect with a partner through shared positive feelings is likely to be conducive to greater intimacy in a relationship.”^[1] 

Sure, there’s a time and a place for serious, deep questions. But these silly romantic questions are perfect for keeping the love alive in a fun way.

Funny Questions to Ask Your Boyfriend to Make Him Laugh

1. What superpowers would you have if you could choose two? What would you do with them?
2. If you lost a hand and had to choose between having a hook or having a perfectly functioning new hand that would always stink of dead fish, which would you choose?
3. Where do your balls go when you ride a bicycle?
4. Would you stake me if I turned into a vampire, or would you let me turn you too?
5. For the rest of your life you can only eat your least favorite food served on a plate or your favorite food licked off my feet. What do you choose?
6. If the Purge happened in real life, what usually illegal thing would you do, and why would you do it?
7. If we swapped bodies for a day, what would you do with my body, and what would you want me to do with yours?
8. If we were stranded somewhere, starving to death, would you let me eat you so that I could live longer?
9. If I were half fish, would you rather my top half or my bottom half was the fish half?
10. Would you rather live without your skin or without your bones?
11. If you were a Spice Girl, what would your Spice Girl name be?
12. Would you rather have sex with an animal but nobody would ever know or not have sex with an animal but everyone thinks you did?
13. What is your favorite dinosaur?
14. If you could have any mythical creature as a best friend, which one would you want? 
15. If you had to eat one crayon, which color crayon would you choose?
16. What would your name be if you were a girl?
17. Do you think Transformers need car insurance?
18. What’s the first rule of Fight Club?
19. If we were to play hide and seek, where would you hide right now?
20. Do you think we will do well as a team when the zombie apocalypse comes? What qualities and skills do you think we will both bring to the table?

Asking random and ridiculous questions is a good way to show your fun side and to learn new things about your partner. A lot of these questions should be followed up by more questions, so you can get to the reasoning behind their answers and find out what drives them in life. 

According to research from the University of Western Ontario, people prefer to date others who have a good sense of humor. But in the long run, if partners share a similar sense of humor, they will be more satisfied in their relationship, and if they don’t, well, they won’t be quite so happy together.^[2] 

If you make one another laugh every day, it can only enhance your relationship. 

Sexual Questions to Ask Your Boyfriend to Make Him Laugh

1. Want me to bite you? Where?
2. How would you feel if I refused to have sex with you unless you wore an Iron Man mask throughout, every time? Would we still have sex? 
3. What sequence of emojis would you use to describe your sex life?
4. Would you prefer an afternoon nap or some afternoon delight?
5. You can only use one sexual position for the rest of your life — what is it?
6. Have you ever been caught having sex, and if so, did you stop or keep going?
7. What is one thing you have tried in the bedroom that you never want to try again because it was so awful?
8. What is the weirdest thing you’ve ever masturbated to?
9. Where is the weirdest place you’ve ever had sex?
10. Is that an erection in your pocket or are you just pleased to see me?

If you’re secure enough in your own skin to hear about your partner’s past exploits (sexploits?) then these personal questions are for you. 

Beyond knowing your partner’s sexual history, which you absolutely should, questions like this can break the ice and, as long as you’re not both Puritans, lead to some laughs. It also might give you some clues about the best turn-on to use with him. 

Just remember, don’t ask any juicy questions you don’t want to hear the answers to.

Dirty Questions to Ask Your Boyfriend to Make Him Laugh

1. If your penis had to be the shape of a vegetable, what vegetable shape do you think I would enjoy the most?
2. If you could have me dress up as any fantasy character for sexy time, who would it be? 
3. Do you think it would be faster to remove my underwear with a hockey glove or a baseball glove?
4. Would you prefer to watch people having sex or be watched while you are having sex?
5. Will you pretend to be a carpenter so you can nail me?
6. Have you ever thought about a cartoon character from your childhood during sex?
7. Are you a stalker? Do you want to hide in my bush?
8. If I were a PlayStation controller, which part of me would be your favorite button?
9. If I could only have one orifice in my body, and you were the one that had to choose it, which hole would you leave me with?
10. What happened in the weirdest sex dream you have ever had?

It’s important in most romantic relationships — of course there are exceptions — that the sexy spark is kept alive and that both sides feel attractive to the other. 

According to an article from the National Library of Medicine, studies show that “body valuation by a committed male partner is positively associated with women’s relationship satisfaction when that partner also values them for their non-physical qualities.”^[3]

Nonphysical as in . . . sense of humor. 

These dirty but funny questions can help you to discover intimate things about one another in a lighthearted way. They’re also more fun than having things fizzle out when you get bored with the same old program. 

And, for bonus points, they’ll heat things up in the bedroom. 

Flirty Questions to Ask a Guy to Make Him Laugh

1. If I were a cute little ghost, would you peek under my sheet?
2. Have you ever stolen anything — besides my heart?
3. If I was a dessert, what would I be?
4. If our relationship was a rom-com, how would we have gotten together?
5. Does your penis have a name?
6. We are two scoops of ice cream on a cone. What flavors are we?
7. Are you on Santa’s naughty or nice list?
8. Hey, Aladdin, wanna see my magic carpet?
9. If you had to eat breakfast off my naked body, what breakfast food would you choose?
10. Do you want to be the little spoon or the big spoon?

Flirting is so much fun, and it makes people feel good. 

An article from the University of Pennsylvania’s Penn Journal of Philosophy indicates that flirting is not only used to show sexual attraction, and to assess and explore the potential for a good partner, but also to increase intimacy in an existing relationship. It explains, “On the other hand, people often flirt simply because it represents an enjoyable form of interaction.”^[4]

Like I said, it’s fun!

So bat your eyelashes, giggle, flip your hair around in a sexy manner, and ask him flirty questions.

Conclusion

There’s no shortage of questions to ask your boyfriend to make him laugh out loud. While you’re exploring these, I bet you’ll come up with many more funny questions of your own.

Hopefully, they will give you and your man lots of laughs together. Questions like these will lead to intimate conversations where you can both learn a lot — about one other, yourselves, and your relationship. 

Need some more tips and advice on Being in a Relationship? Check link here!

References

1. Chong, J. (2014). Love and laughter: Attachment style and the use of humor when emotionally supporting a relationship partner. The UC Davis Undergraduate Research Journal, 16, 1–12. https://academia.edu
2. Caird, S. M. (2011). Laughter and love: The role of humour styles in dating relationships [Master’s thesis, Western University]. Western Libraries Digitized Theses. https://ir.lib.uwo.ca/cgi/viewcontent.cgi?article=7246&context=digitizedtheses
3. Meltzer, A. L., & McNulty, J. K. (2014). “Tell me I’m sexy…and otherwise valuable”: Body valuation and relationship satisfaction. Personal Relationships, 21(1), 68–87. https://doi.org/10.1111/pere.12018
4. Chang, E. (2017). The evolutionary function of flirting. Penn Journal of Philosophy, 3(1). https://repository.upenn.edu/server/api/core/bitstreams/0e68aba5-18b4-4745-bd55-8b351b3f64ae/content