250 Funny Questions to Ask Your Boyfriend To Make Him Laugh

There’s something magical about making your boyfriend laugh—it can lighten the mood, strengthen your bond, and help you explore each other’s unique quirks. Funny questions are a playful way to break routine conversations and discover new sides of the person you’re dating. For deeper connection, here are the best funny questions that help you get to know him better with a bit of humor. So, get comfy, grab a snack, and let the silly, weird, random fun begin!

Fun Questions to Ask Your Boyfriend

• If you were in charge of creating a brand-new holiday, what would it celebrate?
• What’s the funniest prank you’ve ever pulled on someone (or had done to you)?
• If you could have an unlimited supply of one junk food for life, what would you pick?
• Which cartoon character do you relate to the most, and why?
• What movie instantly puts you in a good mood, no matter how many times you watch it?
• If you could give yourself a ridiculous nickname, what would it be?
• What’s the silliest fear you had as a kid that still makes you chuckle now?
• You’re an action figure—what two accessories do you come with?
• If you were a stand-up comedian, what would your signature joke be about?
• Which superpower would you use strictly to make your life more comfortable?
• If you had to karaoke one song every night for a month, which would you pick?
• Do you think you could survive without your phone for 48 hours? Why or why not?
• What’s your go-to dance move when no one is watching?
• If you could only wear one color for the rest of your life, what color would it be?
• Which fictional villain do you find weirdly charming or kind of cool?
• If you ran a food truck, what would be your best-selling (yet bizarre) dish?
• Which piece of clothing in your closet best describes your personality?
• If you had to pick an animal sidekick, which one would complement your personality perfectly?
• Would you rather always speak in rhymes or only talk in questions for a day?
• If you had the power to read minds for 10 minutes, whose mind would you pick?
• What’s the most embarrassing fashion trend you followed when you were younger?
• If you were a circus performer, what act would you do horribly but try anyway?
• What’s a TV show you secretly love but would never publicly admit?
• If you could design a roller coaster, what would be its weirdest feature?
• If you had a personal theme song that played whenever you walk, what would it be?
• Who would you choose as your sidekick in a zombie apocalypse scenario?
• If you could only eat breakfast foods all day or dinner foods all day, which do you choose?
• What’s your favorite ridiculous conspiracy theory, even if you don’t believe it?
• Which famous movie quote do you overuse in daily life?
• If you could crash any historical event, which one would you show up for uninvited?
• You have to rename yourself—what’s the funniest name you can think of?
• If you could live in any cartoon universe for a week, which one would it be?
• What’s your most impressive but totally useless talent?
• If you found a genie in a lamp, what’s the most trivial wish you might actually make?
• Which fruit or vegetable would you choose as your personal mascot and why?
• If you had to pick a new color for the sky, what would you paint it?
• What’s your strategy for tackling a buffet—desserts first or main course first?
• If you were made of candy, which part of you do you think people would try to eat first?
• How would you describe your sense of humor using just one word?
• Which actor would definitely lose a fight against you, no questions asked?
• If you could have a pet dinosaur, which one would suit your lifestyle best?
• What’s the weirdest Halloween costume you’d be willing to wear if I dared you?
• If you had to adopt a medieval weapon as your everyday tool, which one would you pick?
• Which celebrity do you think you’d most likely become BFFs with, and why?
• If you could replace your left hand with something else functional, what would it be?
• What’s your most cringe-worthy cooking disaster story?
• Would you rather wear clown shoes for a month or a clown wig for a month?
• If your life were a video game, what cheat code do you desperately need?
• Which mythical creature would be your best bud, and what’d you do together?
• If you were to open a theme park, what would be its bizarre main attraction?

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Weird Things to Ask Your Boyfriend

• What’s your guilty pleasure band or music genre that’s totally out of character for you?
• If you could speak to one inanimate object, which one would it be, and what’s your first question?
• Which cryptid (like Bigfoot or Loch Ness Monster) do you secretly hope is real?
• Would you rather have fingernails made of spaghetti or hair made of cotton candy?
• If you could see smells, what color do you think your favorite food would be?
• What’s the strangest superstition you kind of believe in?
• If your belly button could dispense any condiment, which would you choose?
• Which historical figure would be the worst roommate for you and why?
• If you had a pet rock, what would you name it and how would you decorate it?
• Would you rather always have wet socks or an itchy sweater you can’t remove?
• What’s your best argument for why aliens haven’t visited us yet?
• If you could only communicate via memes for a day, how would that day go?
• Which part of your daily routine would be most hilarious if reversed?
• If you had to spend a day living inside your favorite video game, which would you pick, and why?
• What weird theme would you choose for your dream house’s interior design?
• Would you rather have a boombox follow you around playing theme music or a personal paparazzi?
• If your shadow had a mind of its own, what mischief would it cause?
• You can replace your reflection in mirrors with a cartoon version of yourself—would you do it?
• If you could taste words, which word do you think would taste the best?
• What’s the oddest dream you’ve ever had that still confuses you when you think about it?
• If animals could talk, which one do you think would be the most annoying, and why?
• Which weird fear or phobia do you kinda get, even if you don’t have it?
• If you could only communicate through fortune cookies, what message would you slip people?
• If you had to rename Earth to something bizarre, what would it be?
• Which mythical power would you want if it only worked half the time?
• If you could shrink down to ant-size for a day, what’s the first thing you’d do?
• What’s the strangest thing you believed as a child that still haunts you?
• If your life was a horror film, what would the monster be made of?
• Would you rather have a tail that wags when happy or ears that droop when sad?
• What bizarre law would you create if you ruled the world for one day?
• If you could rebrand a planet in our solar system with a whimsical name, which planet and name?
• You can only eat food that’s purple for a week—do you survive or go insane?
• If you accidentally conjured a mini storm cloud that follows you around, how would you cope?
• If all your furniture could talk, who do you think would gossip the most?
• Would you rather have hands that glow in the dark or feet that squeak like rubber ducks?
• If you had to produce a bizarre perfume, what notes would it include?
• Which conspiracy theory do you think would be funniest if it turned out true?
• What’s the weirdest competition you’d totally dominate (e.g., burping the alphabet)?
• If you had to become a mutant fruit, which fruit would you combine yourself with?
• Would you rather live in a house with secret tunnels or secret trapdoors everywhere?
• If you found a hidden room in your house, what weird theme would you decorate it with?
• If you had a personal soundtrack that only played awkward music, would you keep it anyway?
• Which fairy tale would be the creepiest if it happened in modern times?
• You’re a ghost—what’s your signature haunting style?
• If your sneeze sounded like a random animal call each time, which animal call would amuse you the most?
• Which strange fact about you would you hide from future aliens if they visited?
• If you had a horse-sized hamster, what would be the best strategy to feed it?
• Would you trade places with your favorite cartoon villain for a day, and what chaos would you cause?
• If you had to choose between never washing your hair or never washing your feet again, which would it be?
• Which bizarre hairstyle would you try once if no one could judge you?

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Random Questions to Ask Your Boyfriend

• If you were a flavor of ice cream, which flavor would match your mood right now?
• What’s a hobby you’d secretly love to try, but haven’t told anyone about yet?
• If you had a 60-second commercial about yourself, how would you pitch “you”?
• Which childhood TV show do you think shaped your sense of humor the most?
• If you could have dinner with any fictional character, who would it be?
• What’s a common saying that you think is totally overrated or makes no sense?
• If you could live in any country for a year, just for fun, where would you go?
• Which random everyday item do you have strong, borderline irrational opinions about?
• If time travel were possible for one afternoon, what would you do first?
• Which random skill—like juggling or whistling—do you wish you instantly mastered?
• Have you ever had a recurring dream that you still remember?
• What’s the last thing that made you laugh out loud unexpectedly?
• Which app on your phone could you not live without, purely for entertainment?
• If your favorite band wrote a song about you, what would the title be?
• Do you have a go-to YouTube video you watch when you need a mood boost?
• If you had to teach a spontaneous workshop on any random topic, what would it be?
• What odd piece of trivia do you bring up way more often than you should?
• If you were forced to be an expert in one completely useless thing, what would it be?
• Who in your life do you think would be the best travel companion on a no-plan road trip?
• If you could give every human on Earth one piece of advice, what would it be?
• What’s something you tried that you thought you’d hate but ended up loving?
• If you won a lifetime supply of something random (like socks), would you enjoy it or get bored?
• What’s your unusual comfort food combination that other people might judge you for?
• If you found $100 in a random place, what’s the most spontaneous thing you’d buy?
• Which weird personality test result (like “Which sandwich are you?”) have you found shockingly accurate?
• What’s the strangest compliment you’ve ever received?
• If you could remove one common word from the English language, what would it be and why?
• You can only watch one movie on repeat for a year—what’s your somewhat weird choice?
• Which social media platform would you delete forever if you had the power?
• What’s the weirdest conversation you’ve overheard in public?
• If you could have a cameo in any film or TV show, which would you pick?
• Would you rather your phone’s autocorrect always be wrong or never exist at all?
• What’s a small thing that can completely make your day when it happens?
• If you had the power to speak any language instantly, which would you choose to impress people?
• You can invite any five random historical figures to a dinner—who’s on your oddball guest list?
• If a genie told you to choose between 100 free pizzas or 10 free flights, which do you pick?
• What random thing are you absolutely terrible at, even though you’ve tried?
• If you could rename common household items (like the fridge), what silly name might you give them?
• If a coffee brand offered to sponsor your life, would you say yes or prefer another brand?
• What’s the most bizarre text message you’ve received and couldn’t stop laughing at?
• If you had to do a random job for a day—like be a clown or a lifeguard—what would you pick?
• Which fictional or mythical place do you wish existed in real life for you to visit?
• Do you think you could handle being a reality TV star for a week, or would you go nuts?
• If your sense of humor was a shape or pattern, how would you describe it?
• What’s the weirdest outfit you secretly want to try but haven’t mustered the courage to wear?
• Which common piece of life advice do you think is actually kind of silly?
• If you had to live in a house that was completely themed—like a jungle or a spaceship—what would it be?
• Do you have any random weird talents, like eyebrow dancing or ear wiggling?
• Which music genre is your ultimate guilty pleasure, that no one would suspect?
• If you could fill a swimming pool with something other than water, just for fun, what would it be?

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Silly Questions to Ask Your Boyfriend

• Would you rather be able to talk to pigeons or have them deliver your mail?
• If you woke up tomorrow with feathers instead of hair, how would you style them?
• Which fruit do you think would win in a fight: a pineapple or a watermelon?
• If you had to serenade your reflection in the mirror, what tune would you hum?
• You’re forced to invent a new handshake—how weird would you make it?
• If you wrote a “How to Be Silly” manual, what would the opening chapter say?
• Which cartoon sound effect best captures your reaction to unexpected news?
• If someone challenged you to a silly walk-off, how would you describe your signature move?
• You can send an anonymous silly gift to anyone—what would it be and to whom?
• If you opened a restaurant where only awkward dishes are served, what’s on the menu?
• What ridiculous alternate name would you give to a giraffe if you discovered the species?
• Would you rather have bacon-scented breath or bubble gum-scented hair for a week?
• If “tickle fights” were an Olympic sport, would you compete or watch from a distance?
• Which superhero would be funniest if they had to wear an oversized, squeaky clown nose?
• You have to adopt one silly tradition, like “High-Five Fridays”—what do you pick?
• If you could only communicate with comedic sound effects, which ones would you overuse?
• Would you rather do a polar bear dip in a kiddie pool or run a 50-yard dash in clown shoes?
• If your dream job was “professional goofball,” what would be your daily duties?
• Which children’s nursery rhyme do you secretly still find unexplainably catchy?
• If you had to invent a new dance craze, what weird body movements would it involve?
• Which mythical creature would have the silliest accent if it could talk?
• If you were the voice actor for a cartoon donkey, how would you make it stand out?
• If you could swap laughter styles with a cartoon character, whose would you choose?
• Would you rather have bananas for fingers or grapes for toes for one day?
• If there was a jingle that played every time you entered a room, how would it go?
• If your phone could only speak in puns, how quickly would you silence it?
• Which household chore could be turned into the silliest competition among friends?
• Would you rather have your eyelashes beep whenever you blink or your knees squeak when you walk?
• If you had a catchphrase, what borderline absurd expression would it be?
• You invent a new holiday celebrating pure silliness—what’s the main tradition?
• If your snore had an auto-tune feature, what kind of remix would it create?
• If you had to embody a silly meme in real life, which one would represent you best?
• If you had a side hustle as a “Professional Silly Photo Bomber,” how would you sabotage photos?
• Would you rather have a pet turtle that tells corny jokes or a parrot that repeats them?
• If you were asked to star in a comedy sketch, which weird props would you insist on?
• What’s your secret (or not-so-secret) comedic catch to make me laugh in public?
• You must wear a costume for a whole day—clown, alien, or giant banana suit: pick one!
• If you replaced your daily greetings with dance moves, how would you greet your best friend?
• Which classic kid’s game would be your new form of exercise if you had to choose (hopscotch, freeze tag, etc.)?
• If everyone around you suddenly spoke like Muppets, how would you respond?
• If you had to invent a silly snack flavor, what bizarre combo would actually be tasty?
• If you could only giggle in the style of an evil cartoon villain, would you embrace it or try to hide it?
• Which inanimate object would you like to see come to life and try stand-up comedy?
• Would you rather be stuck in a room full of squeaky toys or whoopee cushions for an hour?
• If you turned into a baby goat for a day, how would you have the most fun?
• What’s the silliest disagreement you’d be willing to have publicly?
• If you had to design a silly T-shirt line, which phrase do you think would sell best?
• You’re given a jester’s hat—do you wear it everywhere for a week or hide it in shame?
• If you discovered you could talk backward flawlessly, how often would you show off?
• Would you rather be a teacher for a day in a clown college or a librarian in a cartoon city?

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Fun Things to Talk About With Your Boyfriend

• Childhood Adventures: What silly or risky escapades did you pull off with your friends?
• Comedy Crushes: Which comedian do you secretly wish was your best friend?
• Travel Fantasies: If budget didn’t matter, what weird but fun location would you jet off to first?
• Prank Tales: Share your best or worst prank moment—on the receiving or giving end.
• Funny Bucket List: Name three wild activities you’d love to try (like bungee jumping in a banana suit).
• Silly Phobias: Ever been freaked out by something super random?
• Cartoon Crossover: If you could meld two cartoon universes for an ultimate show, which would you pick?
• Accidental Embarrassments: Talk about the time you wore your shirt inside out all day.
• Food Debates: Which ridiculous “food hack” are you actually curious to try?
• Imaginary Pets: If you could keep a mythic creature as a pet, which would it be and how would daily life look?
• Reality Show Pitches: Invent a new reality show that’s so silly, it might just work.
• Meme-Worthy Moments: Which personal stories from your life would become an instant meme?
• Craziest Dreams: Let’s compare dream plots—who had the wildest storyline last night?
• Random Talents: If you were forced to show off at a talent show, what weird skill would you showcase?
• Personality Quizzes: Which quiz question always stumps you with its strangeness?
• Favorite Childhood Obsessions: Remember that one cartoon or toy you’d never part with?
• Creative Business Ideas: If you had to open a business tomorrow, what whimsical concept would you run with?
• Ridiculous World Records: Which record could you realistically (or maybe not) break?
• Public Dare Stories: Any time you did something silly in public just for the thrill of it?
• Cooking Mishaps: Share comedic kitchen disasters that ended up being a great story.
• Family Quirks: Is there a bizarre tradition in your family that cracks you up?
• Funniest One-Liners: Any quick jokes or quotes that always make you laugh?
• Dream Gadgets: If you invented a bizarre gadget, what problem would it fix?
• Nostalgic TV: Which old shows do you wish had a silly reboot now?
• Bad Advice Exchange: Swap the most hilariously bad advice you’ve heard.
• Karaoke Disasters: Ever tried belting out a song you completely butchered?
• Favorite Chips or Snacks: Argue over which flavor is the absolute best in a comedic debate.
• Pet Peeve Laughs: Talk about your strangest pet peeves that others find amusing.
• Conspiracy Fun: Dream up the most outlandish conspiracy theory for pure entertainment.
• Mystery Questions: If you could solve one historical mystery just for fun, which would it be?
• Favorite Stand-Up Bits: Share the comedic routines you can’t get enough of.
• Personal Catchphrases: Does your daily speech have a recurring line?
• Dorm Life Stories: If you lived in a dorm or similar, what’s your funniest memory?
• Birthday Traditions: Talk about the weirdest or coolest birthday tradition you’ve seen or tried.
• Survival Situations: If you got stuck in a supermarket overnight, how would you entertain yourself?
• Alien Scenario: If aliens landed and asked for entertainment, what show or game would you present?
• Friend Group Quirks: Does your friend circle have jokes only you guys get?
• Tech Fails: Ever had a phone or computer glitch that was comedic gold?
• Vacation Gone Wrong: Laugh over that time you planned a trip that turned into a comedic fiasco.
• Worst First Impressions: Reveal a story about meeting someone with a weird handshake or intro.
• Music Guilty Pleasures: Open up about a track you can’t stop jamming to but might be embarrassed about.
• Urban Legends: Heard any local legends that are more silly than scary?
• If YouTube Awards Existed for You: Which weird category would you dominate in?
• Re-Live a Day: If you could re-live one comedic day from your past, which would it be?
• Fictional Pet Peeves: If you had to scold a TV or movie character for their nonsense, who would it be?
• Odd Social Etiquette: Have you observed any unwritten social rules that are just plain funny?
• Secret Rooms: If your house had a hidden room, how would you decorate it and use it?
• Random Talent Competitions: If you could create a new type of Olympics for random skills, what event would you compete in?
• Quarantine Pastimes: Did you pick up any bizarre hobbies when you had extra time?
• Invention Brainstorm: If you had to pitch one silly product on a shopping channel, what would it be?

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Making the Most of These Questions

Things to Know

• Gauge His Mood: If your boyfriend’s having a chill or slightly silly day, these questions will fit right in. If he’s stressed, you might ease in with something light before going for the really weird stuff.
• Keep It Balanced: While it’s great to ask comedic questions, mix in moments of genuine follow-up. Humor plus real curiosity fosters deeper connection.

How to Use Them

1. Game Night: Turn these questions into a card game or quiz you can pull from whenever you need a laugh.
2. Road Trip Ammo: Jot down a few on your phone for a long drive. It keeps boredom at bay and the conversation lively.
3. Text Prompts: Send him one random question per day and see how funny or surprising his replies get.

FAQs

1. What if he’s not into goofy questions?
   • Try choosing milder ones first. You can always test the waters with something slightly offbeat before going all in.
2. Should I answer them too?
   • Absolutely. Make it a shared experience. Hearing your silly answers can encourage him to open up more.
3. Do I have to ask all 50 at once in each category?
   • Definitely not. Pick a few you like. Let the conversation flow naturally; the point is to have fun, not to blast through them as a checklist.

Closing Thoughts

Asking funny questions can turn an ordinary chat into a memorable moment, revealing a playful side of your boyfriend (and yourself) that might otherwise stay hidden. By weaving in humor, you’re not just entertaining each other—you’re also strengthening your bond through shared laughter and quirky insights. Feel free to adapt these prompts or create your own spinoffs. After all, the best part about a relationship is the endless ways you can discover more about each other, one hilarious question at a time. Enjoy!