200 Funny Questions to Ask Your Boyfriend What to Talk About Make Him Laugh

Alright, let’s get this party started. You’re here because you’ve hit that point in the relationship where the standard “How was your day?” just isn’t cutting it anymore. We’ve all been there! You want to connect, to really talk, but you also want to keep things light, fun, and maybe even a little ridiculous. Because let’s be honest, nothing beats the feeling of making your partner genuinely laugh.

I’ve always believed that shared laughter is the secret sauce to a great relationship. It’s the glue. So, I’ve put together this massive list of 200 funny questions to ask your boyfriend. Think of it as your secret weapon against boring conversations. We’re going to break them down into categories because, hey, even chaos needs a little organization. Ready to become the funniest person he knows? Let’s go.

Why Funny Questions Are Your New Best Friend

Ever found yourself staring at each other over dinner, both secretly scrolling through your phones under the table? Yeah, not a great look. Funny questions do more than just break the ice; they shatter it completely.

They catch him off guard, spark his creativity, and reveal sides of his personality you might not see during everyday chit-chat. It’s not an interrogation; it’s an adventure. You’re not just asking “what’s your favorite movie?” you’re asking “what inanimate object would you choose to be and why?” See the difference? It’s about creating moments, not just exchanging information.

The Ultimate Categories of Chaos

To make this easy to navigate, I’ve sorted these questions into ten hilarious categories. Pick your mood, choose a category, and fire away. IMO, the weirder, the better.

Hypothetical Hilarity: The “What If” Zone

These questions are pure gold for revealing how his brain works. They’re silly, imaginative, and have no right or wrong answer.

1. If you could have any superpower, but it had to be incredibly useless (like the ability to turn left really well), what would it be?
2. You’re the world’s politest zombie. How do you ask someone for their brain?
3. If animals could talk, which species would be the rudest and why? (My money’s on geese. Those guys are savages.)
4. What would be the absolute worst “buy one get one free” sale ever?
5. If you were arrested with no explanation, what would your friends and family assume you had done?
6. You have to replace your hands with something that isn’t hands. What do you choose?
7. If you could only listen to one song for the rest of your life, but it had to be a commercial jingle, which one would you pick?
8. What would be the title of your autobiography and the title of the embarrassing tell-all written by your pet about you?
9. If you had to describe yourself as a type of pasta, what would you be and why?
10. You’re forced to compete in the Olympics. What made-up sport do you have the best chance of winning a gold medal in?
11. If you could instantly become an expert in something ridiculous, like competitive dog grooming or yodeling, what would it be?
12. What completely normal everyday activity would look the most suspicious if done while wearing a full tuxedo?
13. If all your clothes had to be one bright, neon color for a year, which color would you choose?
14. You’re given a million dollars to spend in 24 hours, but you can’t buy anything that retains its value. What’s your plan?
15. If you could add one completely nonsensical rule to a popular sport, what would it be? (e.g., Soccer, but the goalie is on a unicycle.)
16. What would be the worst possible name for a boat?
17. If you could communicate with one type of animal, but only to argue with it, which animal would you pick?
18. What inanimate object do you think has the worst job?
19. If you had to lose one of your five senses, but could gain a ridiculous new sense in return (like sensing when someone is mildly annoyed), what would you trade?
20. You have to start a cult based on a mundane household item. What’s your item and what are your teachings?

Goofy “Would You Rather” Scenarios

The classic game, but we’re turning the absurdity dial up to eleven. These are guaranteed to spark a debate.

1. Would you rather have to speak in rhyme for the rest of your life or have to sing everything you say?
2. Would you rather fight one horse-sized duck or 100 duck-sized horses?
3. Would you rather have a permanent, friendly, but very chatty parrot on your shoulder or have your phone loudly narrate your every text as you type it?
4. Would you rather have to wear swim flippers everywhere you go for a year or have to wear a snorkel indoors for a year?
5. Would you rather have every light you turn on be strobe lighting or have every song you hear be played at half-speed?
6. Would you rather be an amazing singer but only when you’re in the shower, or be an amazing dancer but only when no one is watching?
7. Would you rather have to high-five everyone you meet or have to give a detailed, whispered weather report to everyone you meet?
8. Would you rather your sneeze sound like a chipmunk squeak or your laugh sound like a car alarm?
9. Would you rather have to read every book out loud in a celebrity impression or have to cook every meal while blindfolded?
10. Would you rather be permanently slightly sticky or permanently slightly damp?
11. Would you rather have to answer your phone by yelling “AHOY HOY!” or end every call by saying “Over and out, captain!”
12. Would you rather have a personal theme song that plays whenever you enter a room, or have a dramatic slow-clap follow you after every minor accomplishment?
13. Would you rather have to replace the word “the” with “a” in every sentence or have to replace every noun with the word “potato”?
14. Would you rather have to wear a different silly hat every day for a year or have to wear the same pair of mismatched socks for a year?
15. Would you rather be an expert in a skill that is 100 years outdated (like blacksmithing) or a skill that won’t be useful for 100 years (like Mars colonization guide)?
16. Would you rather have to whisper everything you say or shout everything you say?
17. Would you rather have a rewind button for your life or a pause button?
18. Would you rather have an unlimited supply of one kind of food that you have to eat for every meal, or have every meal be a surprise you can’t choose?
19. Would you rather be famous for something embarrassing or be incredibly wealthy but everyone thinks you’re a total fool?
20. Would you rather always have to say everything that’s on your mind or never be able to speak again?

Quirky Personal Deep Cuts

These questions are funny but can also lead to surprisingly deep and personal conversations. It’s a win-win.

1. What’s the most embarrassing fashion phase you went through?
2. What’s a hill you’re willing to die on that is completely trivial? (For me, it’s that pineapple does belong on pizza. Fight me.)
3. What’s the weirdest thing you’ve ever done when you thought no one was looking?
4. What’s a completely irrational fear you have? (Mine is that ducks might be secretly judging me.)
5. What’s the most childish thing you still do?
6. If your childhood pet could have sued you for one thing, what would it be?
7. What’s the most ridiculous thing you’ve ever cried over?
8. What’s a song you’re secretly ashamed of loving?
9. What’s the strangest dream you’ve ever had that felt 100% real?
10. What’s the most unhinged text in your camera roll right now?
11. What’s a movie you loved as a kid that is absolutely terrible when you watch it now?
12. What’s the worst piece of advice you’ve ever been given, and did you follow it?
13. What’s a food you pretend to like to seem more sophisticated?
14. What’s your most controversial food opinion?
15. If your life was a sitcom, what would the opening credits sequence look like?
16. What’s the most embarrassing way you’ve ever injured yourself?
17. What’s a useless skill you’re weirdly proud of?
18. What’s the strangest rumor that was ever spread about you?
19. If you had to be a character from any commercial, who would you be?
20. What’s the cringiest phase of your internet history?

Relationship Revelations with a Twist

Funny questions about your relationship that are way more interesting than “where do you see us in five years?”

1. If we were a buddy-cop duo, what would our intro sequence be?
2. What’s the most ridiculous argument you think we’ll ever have in the future?
3. If our relationship had a smell, what would it be and why?
4. What animal would you compare me to when I’m hangry?
5. If we had to create a secret handshake right now, what would the first move be?
6. What would be the absolute worst couple’s costume you can imagine us wearing?
7. If our love story was a genre of movie, what would it be? (Disaster film? Romantic comedy? Horror? Be honest.)
8. What’s a totally minor and insignificant habit of mine that you find secretly endearing?
9. If you had to describe our relationship using only three emojis, which would you choose?
10. What’s the silliest thing you’ve ever done to impress me?
11. If we started a band, what would our name be and what instruments would we play?
12. What would the title of the rom-com about our meeting be?
13. If we could swap bodies for a day, what’s the first thing you’d do?
14. On a scale of “well-oiled machine” to “three raccoons in a trench coat,” how would you rate our teamwork on a project like assembling IKEA furniture?
15. If you could give me a superlative award (e.g., “Most Likely to…”), what would it be for?
16. What’s a weird couple tradition you’d want us to start?
17. If we were stranded on a desert island, what’s the one non-essential item you’d hope I packed?
18. What’s the most embarrassing song you’d dedicate to me?
19. If our relationship had a theme song that played every time we entered a room together, what would it be?
20. What’s a completely unrealistic superpower you wish I had to make your life easier?

Embarrassing & Awkward Adventures

Time to dig up those cringey, hilarious memories from the past. These are great for bonding over shared human awkwardness.

1. What’s the most embarrassing thing your parents ever did to you in front of your friends?
2. What’s the worst haircut you’ve ever had?
3. What’s the most awkward encounter you’ve ever had with a celebrity?
4. What’s the most embarrassing thing you’ve ever had to buy at a store?
5. What’s the funniest wrong-number text you’ve ever received or sent?
6. What’s the most awkward thing that’s ever happened to you on a date? (Before me, of course. I hope.)
7. What’s the most ridiculous lie you told as a kid that you thought was brilliant?
8. What’s the most embarrassing thing you’ve ever been caught doing?
9. What’s the strangest thing you’ve ever done to try and get out of a social obligation?
10. What’s the most awkward thing you’ve ever said to a police officer or authority figure?
11. What’s the most embarrassing nickname you’ve ever had?
12. What’s the worst present you’ve ever given someone?
13. What’s the most awkward thing you’ve ever had to apologize for?
14. What’s the funniest time you’ve ever gotten lost?
15. What’s the most embarrassing thing you’ve ever posted on social media?
16. What’s the worst pickup line you’ve ever used, or had used on you?
17. What’s the most awkward thing that’s ever happened to you in a public bathroom?
18. What’s the most ridiculous thing you’ve ever done for a dare?
19. What’s the most embarrassing thing you’ve ever Googled?
20. What’s the most awkward thing you’ve ever said to a waiter or cashier?

Pop Culture & Geekery Gone Wild

For the movie buffs, gamers, and internet dwellers. These questions are a deep dive into his unique brand of nerdiness.

1. If you could be any video game character, but only during their most embarrassing glitch, who would you be?
2. What’s a terrible movie you’ll always stop to watch if it’s on TV?
3. Which fictional character would be the most boring to meet in real life?
4. If you could add one character from any show or movie to the Avengers, who would it be and why?
5. What’s the most overrated video game of all time, IMO?
6. If you could live in any fictional universe, but only as a background extra, which would you choose?
7. What’s a song that is an absolute lyrical masterpiece of nonsense?
8. Which cartoon character’s life would actually be a total nightmare to live?
9. If you could reboot any movie, but make it wildly inappropriate, which one would you pick?
10. What’s the worst possible casting choice you can imagine for a superhero movie?
11. If you could have one item from any video game, what would it be? (And no, not something useful. Something like the Wabbajack from Skyrim.)
12. What’s a popular meme you just don’t get?
13. If you could have a five-minute cameo in any TV show, which one would it be and what would you do?
14. What’s the cringiest line from a song or movie that you unironically love?
15. If all food now tasted like the food in your favorite video game (e.g., everything tastes like Minecraft stew), would that be awesome or terrible?
16. Which celebrity would you least want to be stuck in an elevator with?
17. What’s a plot hole in a famous movie that still bothers you to this day?
18. If you could make any two characters from different shows/movies fight, who would you pick?
19. What’s the most ridiculous product you’ve seen advertised on a podcast?
20. If your life had a soundtrack, what song would play during your morning routine?

This or That: The Silly Edition

Quick, silly, and perfect for when you want a low-effort laugh.

1. Wizard with a wand that only works half the time or a knight with armor that’s always slightly too big?
2. Ability to talk to plants but they’re all really sarcastic or ability to talk to animals but they only complain about the weather?
3. Always have a dramatic soap opera music cue follow you or always have a laugh track play after everything you say?
4. Have your phone constantly autocorrect to something embarrassing or have your GPS always be 10% wrong?
5. Be forced to wear clown shoes to a job interview or be forced to communicate only through charades at a fancy dinner party?
6. Have a permanent tiny raincloud just over your head or have your shoes squeak loudly with every step on any surface?
7. Be an expert at a sport no one has ever heard of or be terrible but famous at a popular sport?
8. Have to start every sentence with “According to my sources…” or end every sentence with “…but that’s just what they want you to think.”
9. Have a personal jester who follows you around or a personal bard who sings about your every move?
10. Be unable to tell the difference between a muffin and a cupcake or be unable to tell the difference between a salad and soup?

Rapid-Fire Randomness

When you just need a quick, one-sentence question to lob his way. No thinking required, just instant laughs.

1. What’s the worst name for a dog you can think of?
2. What’s the least appropriate song to play at a wedding?
3. What’s the most suspicious way to eat a banana?
4. If you could make one vegetable illegal, which would it be?
5. What’s the worst thing to hear right before you go under anesthesia?
6. What’s the most unprofessional thing for a brain surgeon to say during an operation?
7. What’s the worst thing to say on a first date?
8. What’s the least heroic superhero name you can come up with?
9. What’s the worst possible food to bring to a potluck?
10. If your life was a book, what would the chapter titles be?
11. What’s the worst advice you could give to a tourist visiting your hometown?
12. What’s the most ridiculous law you would enact if you were ruler of the world?
13. What’s the most annoying sound a human can make without using their voice?
14. What’s the worst thing to yell out during a yoga class?
15. What’s the most inconvenient time to break out into a musical number?
16. What’s the least fun “fun fact” about yourself?
17. What’s the worst thing to hear from your pilot over the intercom?
18. What’s the most embarrassing way to die in a video game?
19. What’s the worst thing to find in your hotel bed?
20. If you had to be a ghost and could only haunt one specific object, what would it be?

“How Would You Survive?” Scenarios

These are a little more scenario-based and great for bringing out his inner (and hilarious) survivalist.

1. How would you survive a zombie apocalypse if your only weapon was a spatula?
2. You’ve been hired as a consultant for a heist movie. What’s the most ridiculous way to break into a vault that you’d suggest?
3. How would you explain the concept of a smartphone to a medieval knight?
4. You’re on a sinking ship and can only save three items: a rubber chicken, a roll of duct tape, and a single ski. How do you use them to survive?
5. How would you convince a friendly alien that you are the leader of Earth?
6. You’ve been transported back to the 1800s. What’s the first