Want to make your boyfriend laugh and start a random, funny conversation? Asking him silly and nonsensical questions is a fun way to learn more about him and get you both in a good mood. In fact, laughing and playing with your partner can strengthen your relationship! To help you get the conversation and laughter going, we’ve compiled 100 funny questions to ask your boyfriend, ranging from “would you rather” to random questions about his interests and beliefs.

Things You Should Know

  • Start a funny conversation with "would you rather," "this or that," or hypothetical questions.
  • Make your boyfriend laugh with questions about his childhood, embarrassing moments, and his best impressions.
  • Get to know your boyfriend better by asking about his favorite foods, movies, destinations, and random objects.
1

“Would you rather sing every other word you say or yell every other word?”

  1. Spark a funny conversation with a game of “would you rather.”Play “would you rather” by giving your boyfriend 2 ridiculous scenarios or dilemmas that he has to choose between. Get a conversation going by asking him why he chose his option. Share what you would rather choose after he answers to see how similar or different you think![1]
    • “Would you rather your shoes are always untied or your pants zipper is permanently down?”
    • “Would you rather never listen to music ever again or only listen to your least favorite songs?”
    • “Would you rather forget to buy 1 important item or buy 10 unnecessary items every time you go to the grocery store?”
    • “Would you rather be able to talk to animals or control plants?”
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2

“French fries or tater tots?”

3

“If you were in a zombie apocalypse, where would you hide?”

  1. Put him in an apocalyptic scenario to see what he would do. Maybe he’d sail away to a secluded island while you think it’s best to hole up in a grocery store. This is a fun way to see how he would react to the situation and gives you the opportunity to tease him about his answer. Get creative with the situations you throw him in by incorporating places he goes or people he interacts with.[3]
    • “You just won the lottery but you can only buy 5 things before you have to donate the rest. What do you buy?”
    • “You stumble across a time machine. Do you go back into the past or to the future?”
    • “You’re offered a pill that will make you 50% more attractive or 50% more intelligent. Which one do you choose?”
    • “If you were deserted on an island, but could bring 5 items with you, what would you choose?”
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4

“If you were a power tool, what would you be?”

  1. Fire off a totally random question to give your boyfriend a good laugh. Look around your surroundings and have him choose to be an inanimate object or ask him what body part he’d want an extra of. Some questions don’t have to tell you anything about him, but they can be a great way to lift your boyfriend’s mood when he has a bad day.[4]
    • “If you could be any type of musical instrument, what would you be?”
    • “How many geckos would it take to beat a bear?”
    • “How would you reorder the alphabet?”
    • “If you were a type of drinking glass, what would you be?”
5

“What’s the most embarrassing thing that’s happened to you?”

6

“What’s the funniest nickname you had as a kid?”

  1. Uncover silly moments from his childhood. You might not have known your boyfriend as a kid, so this is a great way to see what he was like. You can tease him about how different he is from his younger self and grow closer from knowing more about him.[6]
    • “What’s something funny you believed in as a kid that you were completely wrong about?”
    • “Did you have a toy you couldn’t live without as a kid? What was it?”
    • “What did you want to be when you grew up?”
    • “Did you have an imaginary friend when you were a kid?”
    • "Were you good or bad as a kid? Were you always in trouble?"
7

“What’s the worst date you’ve ever been on?”

  1. Ask him about funny moments from his past relationships. If you and your boyfriend are still getting to know each other, this is a way to talk about previous partners and crushes and build trust while focusing on the lighthearted, embarrassing moments.[7] Share your answers too so he knows he’s not alone in having awkward experiences.
    • “What’s the most embarrassing moment you had with a crush?”
    • “What’s the cringiest line you’ve used on someone?”
    • “Have you ever been stood up by a date?”
    • “Who was the funniest celebrity crush you had as a kid?”
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8

“What’s your best animal impression?”

  1. Test your boyfriend’s impression skills while making him laugh. Make a game out of your questions to see who can do the best impressions. While you’re both laughing and playing, you're growing closer and building a more satisfying relationship.[8]
    • “What’s your best cartoon impression?”
    • “What’s your best celebrity impression?”
    • “Can you act out your favorite movie scene?”
    • “Can you do a dramatic reading of our most recent texts?”
9

“If you could be any fictional movie character, who would you be?”

  1. Learn about his favorite shows and movies. Understanding the genres, themes, and types of characters he likes to watch might tell you about the kind of person he is.[9] Asking about his favorite movies and shows also gives you an arsenal of potential gift ideas and themed celebrations to plan.
    • “You’re stuck in your favorite movie. How will things go for you? What will happen?”
    • “If you had to watch the same TV show every month, what would you choose?”
    • “What would you title the movie about your life?”
    • “Which cartoon character do you think is most like you?”
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10

“If you could eat only one food for the rest of your life, what would it be?”

  1. Find out what foods your boyfriend likes and dislikes. Questions about food can lead you to surprising places, like your boyfriend's favorite foreign meal or his nostalgic comfort snacks. As a bonus, you will learn what meals you can cook together to continue building your relationship.[10]
    • “What’s the grossest thing you’ve ever eaten?”
    • “What food would you still not eat even if you were starving?”
    • “You have to give up one of your favorite foods for the rest of your life. What do you choose?”
    • “What’s a food that you hate but other people love?”
11

“If you could re-do the day that we met, what pick up line would you use on me?”

13

“You can travel to one place and then can never travel again. Where are you going?”

16

“What’s a useless skill you have?”

  1. Play a silly game of trivia—and make it all about your boyfriend's life. Ask questions about him that are unique and that you couldn’t find out without asking to keep the game fun. You will both grow closer as you laugh and learn random facts about each other.[16]
    • “What’s a random fact that no one knows about you?”
    • “Who is the most interesting person you’ve met?”
    • “What’s your favorite memory?”
    • “What moment or memory will always make you laugh?”

About This Article

John Keegan
Co-authored by:
Dating Coach
This article was co-authored by John Keegan and by wikiHow staff writer, Devin McSween. John Keegan is a dating coach and motivational speaker based in New York City. He runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health. This article has been viewed 49,858 times.
10 votes - 50%
Co-authors: 3
Updated: November 7, 2022
Views: 49,858
Categories: Dating
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