100 Funny Questions to Ask Your Boyfriend

Updated on June 17, 2019
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I'm Tatiana and am a firm believer in the power of holistic healing and home remedies! Apple cider vinegar for the win!

Asking questions is by far the best way to get to know someone, particularly a new boyfriend! What’s even better is tying a bit of humor into the questions to encourage a few laughs during this long “getting to know you” process!

Whether you’re looking for funny questions to ask your boyfriend, or simply some questions that will elicit funny responses, it never hurts to keep the mood light!

Funny and random is the way to be if you want to catch your boyfriend off guard! Take a look at this list of funny questions to ask your boyfriend and take a few!

Be sure to also check out this list of 100+ Funny Questions to Ask a Girl!

Fun Questions to Ask Your Boyfriend

  • If you had a pet unicorn, what would you name it?
  • OR if you could make any animal your pet, what would it be and why?
  • OR if you could become any animal, what would it be and why?
  • What kind of animal am I?
  • If you made up an ice cream flavor, what would be in it?
  • What would you call it?
  • You can only eat one thing for the rest of your time on earth. What do you eat and why?
  • Who was your celebrity crush as a teen?
  • Who was your real crush as a teen?
  • Who’s your current crush?
  • Have you ever watched really terrible children’s television just because you were bored?
  • What’s the worst movie you’ve ever paid to see?
  • Who are you most like, Michael Scott, Dwight Shrute, Andy Dwyer, or Ron Swanson?
  • Kill, screw, or marry: Miss Piggy, the flying dog from Never Ending Story, or Tweetie bird?
  • When was the last time you peed in the pool?
  • What about the sink?
  • How often do you pee in the shower?
  • If you had a really fluffy bunny, what would you name it?
  • If you could give your bunny a super power of some kind, what would it be?
  • If you were a cartoon character, who would you be?
  • Would you rather be turned into a hologram or into 2-dimensions?
  • Nachos. What would you put on yours?
  • You have five dollars to spend on anything you want at the dollar store — what do you buy?
  • Name three random things. Just do it!
  • What are three things you can’t live without?
  • When you were a kid, what did you think being this age would be like?
  • What's the grossest thing you've ever eaten?
  • What’s something you love that other people think is gross?
  • What is the most exotic thing you’ve ever eaten?
  • What's the first thing that comes to mind when I say "Bruce Jenner?"
  • What’s the secret ingredient?
  • If you could do any kind of magic, what kind of magic would you do?
  • Finish this statement: "Look out! It's a _____!"
  • If you were invisible for a day, what would you do?
  • What kind of superpower would you have if you had a choice?
  • What is the best organ?
  • What did you want to be when you grew up?
  • Have you ever pretended to be a woman?
  • Have you ever worn a dress?
  • Have you ever tried walking in heels?
  • Have you ever put on makeup?
  • Do you want to?

Funny Things to Ask Your Boyfriend

  • Has anyone ever walked in on you in the bathroom?
  • What is the most embarrassing thing someone has caught you doing?
  • What is the most embarrassing moment you’ve ever had?
  • If you could legally change your middle name, what would it be?
  • Do you call your muscles “guns?”
  • What’s the most cringeworthy thing you’ve ever said to someone you were attracted to?
  • What is the funniest dream that you had that you can recall?
  • What’s the worst nightmare that you’ve had that you can recall?
  • Will you do your best animal sound for me?
  • Have you ever been streaking?
  • What about skinny dipping?
  • Do you want to?
  • What food do you love, but would hate as a Dairy Queen Blizzard?
  • What’s the food you like to have the most on your birthday?
  • What is your biggest guilty pleasure?
  • What was your childhood nickname?
  • What was your favorite thing to wear as a child?
  • Would you rather crank call or ding-dong-ditch your neighbor?
  • What cartoon character am I most like?
  • What movie is most like your life?
  • What is your favorite chick flick?
  • What is your favorite children’s book?
  • What is your silliest pet peeve?
  • What is your grossest habit?
  • Do you know how to spell antidisestablishmentarianism?
  • What is your lamest skill?
  • When your dog farts, do you leave the room or tough it out?
  • Where was the worst place that you had to fart?
  • How many selfies do you take a day?
  • Do you delete them or keep them?
  • Have you ever looked in the mirror and winked at yourself?
  • Do you ever talk to yourself in the mirror?
  • What is the cheesiest pickup line you’ve ever tried to use on a girl?
  • Did it work?
  • Have you ever been kicked out of a public place?
  • If you were a biker, what would your biker nickname be?
  • What is the best mode of transportation?
  • What’s grosser: Yellow teeth or yellow toenails/fingernails?
  • If there were a food that you absolutely couldn’t give up, what would it be?
  • What is your worst habit?

Video: Cute Gifts for Your Boyfriend

Random Questions to Ask Your Boyfriend

  • How long do you think you’d survive a zombie apocalypse?
  • What would be your weapon of choice in a zombie apocalypse?
  • What is the special skill you would add to a team trying to stay alive during a zombie apocalypse?
  • If you were a character from The Office, which one would you be?
  • If you were a Looney Toons character, which one would you be?
  • If you could be a superhero, which would you be?
  • What is your favorite body part on yourself?
  • If you could have another body part of some kind, what would it be?
  • Which is more important, happiness or intelligence?
  • Are you more happy or are you more intelligent?
  • What animal would you say most describes your appearance? What about your personality?
  • Have you ever kissed another guy?
  • Have you ever made a prank call?
  • What’s the dumbest idea that you’ve ever had that you thought was the smartest idea you’ve ever had?
  • If you go shopping by yourself, what does your shopping list usually consist of?
  • What three things do you consume each week?
  • What word do you find the most humorous?
  • What’s something that always makes you laugh?
  • Do you think you’re funny? Why?
  • Would you rather be a vampire or a zombie?
  • Have you ever tried hitting a target while peeing?
  • How many online dating sites have you tried?
  • If you catch a fish, do you eat it or let it go?
  • Do you scream on roller coasters?
  • What’s the scariest movie you’ve ever seen?
  • Do you wet your toothbrush before or after you put toothpaste on it?
  • What is the most awkward pet name you’ve ever been given?
  • What’s the most awkward romantic situation you’ve ever been in?
  • Did you ever listen to the Spice Girls?
  • What’s a song no one knows that you like?
  • What is your favorite Disney movie?
  • Who’s your favorite Disney princess?
  • Would you rather take a pie to the face or have ice water dumped over your head?
  • Would you ever drive a SmartCar?
  • Would you rather drive a tank or a submarine?
  • If I was a motorcyclist, would you ride on the back?
  • Do you make pictures out of the clouds?
  • If you could draw anything perfectly, what would it be?
  • Do you ever feel tempted to splash in a big puddle?
  • Have you ever felt tempted to commit a crime?
  • If you had to kiss a guy other than family, who would it be?
  • If I am mad at you, what is the safest way to handle it?
  • Do you ever get mad at me?
  • If you could date any celebrity, who would you choose?
  • What about any politician?
  • What is one movie that you wish was real life?
  • If you went to Comic-Con, who would you dress up as?
  • What would you spend $500 on?

Silly Questions to Ask Your Boyfriend

  • If you could dip anything into chocolate and eat it, what would it be?
  • How much do you think this computer weighs?
  • What do you think life will look like in 100 years?
  • Which do you believe in more: the Easter bunny or the tooth fairy?
  • If you could go back in time to any moment, what moment would you go to and why?
  • Which is better: a tiny scarf, or a tiny hat?
  • If you could either not be able to recognize voices, or to not recognize faces, which would you choose?
  • If you had to dip something in mayonnaise and eat it, what would you eat?
  • If your favorite type of noodle came to life and had something to say to you, what would it say?
  • What does your teddy bear think about you?
  • What is your favorite utensil?
  • If you had to eliminate one day of the week, which one would you eliminate and why?
  • What do you think about the most while you’re pooping?
  • What’s the best, brightest idea that you’ve ever had?
  • What would be the most disturbing thing you could find under your bed?
  • You can’t do peanut butter and jelly or peanut butter and honey, so instead you do . . . .
  • If you could put any kind of clothes on a dog, what would you put on it and why?
  • If you could put any kind of clothes on a hot dog, what would you put on it and why?
  • Ireland or Italy?
  • If you could have any foreign accent, which one would you pick?
  • If you could speak any foreign language, what would it be?
  • Have you ever had a manicure or pedicure?
  • If a movie was made about your life, what would the title be?
  • What actor would you pick to portray you?
  • What actress would you pick to portray me?
  • Who would be the director?
  • You find out I'm a KGB spy hired to collect information about you. What do you do?
  • You ask my father for my hand in marriage and he says "Over my dead body!" Do you propose anyways?
  • What’s something that you love and you don’t understand why?
  • Faced with starvation, what would you still never eat?
  • What’s something that you’ve wanted to do for a long time? Why haven’t you done it?
  • If you were the host of a TV show, what type of show would it be?
  • You have three ingredients to make a delicious dish for dinner: what do you make and how?
  • Would you rather go to Hogwarts, to Rivendell, or to the Death Star?
  • If you were on Cutthroat Kitchen, what three dishes would you hope for?
  • Who do we personally know that you would not want to meet under the mistletoe?
  • If you were a wizard in Harry Potter, what would your Patronus be?
  • You're given an ax, a sword, a crossbow, and a stick of dynamite. Which would you use to filet a fish?
  • You're a criminal mastermind — what do you leave at the scene of the crime as your calling card?
  • Have you ever played Candy Crush?
  • What store customer loyalty rewards cards are in your wallet?
  • What’s the most sentimental thing that you have?
  • What's the biggest turnoff: stinky feet, sweaty armpits or bad breath?
  • What is your favorite Britney Spears song?
  • Who are you secretly jealous of?
  • If you had to watch the same movie, once a day for a month, which movie would it be?

Weird Questions to Ask Your Boyfriend

  • What song have you listened to on repeat?
  • You accidentally say "I love you" to your boss. Do you address it or pretend it didn't happen?
  • You think you hear me say “I love you under my breath.” What do you do?
  • You either lose your sense of smell or your sense of taste — which do you prefer and why?
  • I’m going to take a hammer to either your laptop or your mobile phone: which one do you want to lose least?
  • You get to create any kind of holiday that you want! What kind of holiday do you make?
  • What are the rituals and celebrations around this holiday?
  • You get to design a new kind of never-before-seen clothing. What kind of clothing do you make? What does it look like? What do you call it?
  • What are all the positive things that could come from a nuclear apocalypse?
  • If you could create an app that could do anything, what would it be?
  • If your parents looked through your phone, would they find anything surprising in it? What about me?
  • How often do you stop to consider that we might all be holograms or something like that?
  • What is your favorite dance jam?
  • You just won an international award for creating an awesome new dance move. Please demonstrate it for me.
  • If you could be incredibly fit but as smart as a horse, or horribly obese but as intelligent as Richard Dawkins, what would you choose?
  • Would you rather fart every time you yawned or scream every time you sneezed?
  • A genie comes out of your mobile phone and gives you three wishes — what do you wish for?
  • Would you rather go to Mars or Buenos Aires?
  • If you could get drunk with any historical figure, who would it be?
  • What is something only your mom knows about you?
  • What’s something no one besides me knows about you?
  • You left your gym bag in my car. If I opened it, what would I find?
  • If I went through all your stuff in your room, would I find anything surprising?
  • Have you ever watched Twilight?
  • You meet my family for the first time and get hit on by a female family member. Do you tell me about it?

Fun Things to Talk About With Your Boyfriend

  • You’re locked in the mall overnight. What do you do first?
  • You have a magic lamp and something comes out of it that isn’t a genie. What is it?
  • It’s the night before Christmas and you hear footsteps on the roof — what do you do?
  • Either you have to wear a tube top to a wedding, or your mom has to wear a tube top to a wedding that you’re going to as well. Which one do you choose?
  • You can hold your breath for 10 minutes. What do you do with your power?
  • If you could find any kind of buried treasure, what kind of buried treasure would you want to find?
  • What’s better: sitting or standing?
  • Would you rather walk or bike on water?
  • You’ve created your own deodorant brand. What’s its name and mascot?
  • What is the best kind of crime?
  • What is the best color?
  • If you were the dictator of an imaginary country: what would you call it? What would your title be called? What would the traditions of the country be like?
  • What was your first screen name?
  • What is your robot name?
  • What’s the worst date you’ve ever been on?
  • What is the best kind of shoe?
  • If you were a type of instrument, what kind would you be?
  • Sci-Fi or Horror?
  • You can do anything with money except spend it: what do you do?
  • Invent a new piece of technology.
  • What is the best kind of butter?
  • You wake up and find out that everything you touch turns into cotton candy. What do you do?
  • First thing you’d do if you had the place to yourself and a whole bunch of opera costumes?

Keeping Things Fun

Make a date night out of it! Turn on your favorite playlist, get out some snacks and drinks, and chill out on the sofa, asking each other funny questions that will ultimately help you get to know each other better too!

Hopefully by asking him some funny questions, he’ll get into it too and throw some at you! It’s only fair, after all! If you have a good sense of humor, funny questions will probably come natural to you anyway!

And what night isn't better with a little laughter with your love?!

Deep Questions to Ask Your Boyfriend


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    • profile image


      7 hours ago

      He didn’t know what was going on because I just randomly started asking them but he loved the

    • profile image


      5 weeks ago

      Am very interested in this text

    • profile image


      2 months ago

      I really like these he love answering them

    • profile image


      4 months ago

      Was this written by a 12 year old ?

    • profile image


      5 months ago

      wow!!!!add more

    • profile image


      10 months ago

      we love all our firends so much.

    • profile image

      katie-john ANNAILES rowland 

      11 months ago

      i like so much

    • profile image


      24 months ago

      Yo I was talking to my bf on the phone and I asked him all these questions we were wierded out at first but then we got used to it

    • profile image


      2 years ago

      Funneh could you make more videos and funneh I know you I always watch your videos and I subscribed to your channel and have a good day

    • profile image

      everything is cool 

      2 years ago

      Nice love it

    • profile image


      2 years ago

      Amazing questions. I love them.

    • profile image


      2 years ago

      OMDG... These qstns are soo amazing.. I reaally had a good time with my boyfriend

    • profile image


      2 years ago

      hi everyone

    • profile image


      2 years ago

      So many funny ones

    • profile image


      2 years ago

      You ask the best questions

    • profile image


      2 years ago

      it was alot nut it was fun

    • profile image


      2 years ago

      i love the questions you should add 100 more

    • profile image

      Bree Anderson 

      3 years ago

      OMG this is amazing. I'm playing this game with my boyfriend right now.

    • profile image


      3 years ago

      i love this

    • profile image


      3 years ago

      absolutely love the questions


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