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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. With over 10 years of professional experience, 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.
There are 19 references
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This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources.
This article has been viewed 200,925 times.
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.
Steps
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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] X Research source
- “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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Start a silly debate with “this or that” questions. Be creative with your options and make the choices unrelated for a wacky conversation. These questions will highlight you and your boyfriend’s similarities and differences in a funny way! Don’t worry if he loves french fries while you’re a champion for tater tots, it’s actually healthy to have different tastes and interests from your boyfriend. [2] X Research source
- “Beach or mountains?”
- “Dinosaurs or mythical creatures?”
- “Salty or sweet?”
- “Always cold or always hot?”
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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] X Research source
- “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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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] X Trustworthy Source Mayo Clinic Educational website from one of the world's leading hospitals Go to source
- “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?”
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Make him laugh and blush with an embarrassing question. This is a lighthearted way to get him to open up about his past. You can both grow closer and build trust as you share moments and experiences you don’t want anyone else to know about. [5] X Research source
- “Have you ever been caught in a lie?”
- “What’s the weirdest thing you did as a kid?”
- “What’s the weirdest thing I’d find in your search history?”
- “Have you ever sent a text or made a post on social media that you regretted?”
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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] X Trustworthy Source PubMed Central Journal archive from the U.S. National Institutes of Health Go to source
- “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?"
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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] X Research source 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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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] X Trustworthy Source Greater Good Magazine Journal published by UC Berkeley's Greater Good Science Center, which uses scientific research to promote happier living Go to source
- “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?”
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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] X Trustworthy Source Science Direct Online archive of peer-reviewed research on scientific, technical and medical topics Go to source 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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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] X Research source
- “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?”
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Ask him about your relationship to strengthen your bond. Relationship talk doesn’t always have to be serious. Silly questions about yourself and how you met can help you both reminisce about your relationship and reaffirm your love for each other. [11] X Research source
- “If we swapped bodies for a day, what would you do?”
- “What song describes our relationship?”
- “What’s your funniest memory of us together?”
- “What embarrassing nickname would you give me?”
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Increase your connection as you laugh and bond over flirty questions. Asking flirty questions can improve your communication and relationship satisfaction. Your questions can be as silly or suggestive as you’d like. [12] X Research source
- “Who’s your celebrity crush?”
- “What’s your favorite part of my body?”
- “What’s your favorite romantic movie?”
- “What does the perfect date look like to you?”
13
“You can travel to one place and then can never travel again. Where are you going?”
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Open up a conversation about travel experiences and wishes. This is a great way to learn more about your boyfriend’s past. Use his answers to plan a trip together that will help you grow your connection. [13] X Research source
- “If you could live at the bottom of the ocean or on Mars, what would you choose?”
- “What are the top 3 places you want to visit?”
- “If you could have been born in a different country, where would you choose?”
- “What popular destination do you have no desire to visit?”
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Ask about his favorite random objects and things. While it’s useful to know your boyfriend’s favorite foods, movies, and books, useless information is fun and can still help you learn more about him. [14] X Research source Surprise him with random categories and keep him guessing about what you’ll ask next.
- “What’s your favorite tree?”
- “What’s your favorite type of cheese?”
- “What’s your favorite sea animal?”
- “What’s your favorite time of day?”
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Uncover your boyfriend’s wild side. Maybe he’s a secret thrill seeker or had a wild past, but by sharing his funny misadventures you are building trust and vulnerability. [15] X Research source If he is a thrill seeker, start planning some exciting activities that you can do together, like skydiving or zip lining.
- “Have you ever been kicked out of a bar?”
- “Have you ever dined and dashed?”
- “Have you ever crashed a wedding?”
- “Have you ever been skinny dipping?”
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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] X Trustworthy Source Greater Good Magazine Journal published by UC Berkeley's Greater Good Science Center, which uses scientific research to promote happier living Go to source
- “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?”
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Ask questions about magic and powers to understand his personality. Magic and superpowers might not exist in reality, but asking questions about them can be a fun way to see if his answers match up with his real personality. [17] X Research source
- “If you could have any superpower, what would it be?”
- “What psychic ability would you choose to have?”
- “If you had a useless superpower, what would it be?”
- “Would you rather team up with Batman or Superman?”
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Ask about his funny quirks and routines he has at home. If you are spending a lot of time together or want him to move in with you , you want to know your boyfriend’s tendencies and routines. He probably has silly habits that might not make him perfect, but certainly make him more endearing. [18] X Research source
- “Do you wash your hair first or your body first?”
- “What’s your worst habit?”
- “Are you an early riser or do you sleep in?”
- “What 5 things could you not live without?”
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Find out if he believes in the occult or if he’s had ghostly encounters. Chat about the supernatural and other mysterious topics—you might learn that your boyfriend has some surprising, spooky interests. If he doesn’t have any supernatural experiences to share, you can take turns telling spooky stories . [19] X Research source
- “What’s the most outrageous conspiracy that you believe in?”
- “What’s an urban legend that you believe in?”
- “Do you believe in karma?”
- “Do you believe in astrology?”
- "What is your rising sign?"
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Get to a deeper level while keeping the conversation light. You can ask questions that will elicit a funny response, but that your boyfriend can take deeper if he wants. Ask him questions that will help you understand him more as a person while avoiding intense questions. [20] X Research source
- “What’s your greatest dream?”
- “If you could have dinner with anyone in the world, dead or alive, who would you choose?”
- “What’s something you still want to try?”
- “What’s your greatest skill?”
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References
- ↑ https://conversationstartersworld.com/would-you-rather-questions/
- ↑ https://www.huffpost.com/entry/things-couples-dont-need-to-have-in-common_n_5acbfa9ce4b07a3485e796ca
- ↑ https://icebreakerideas.com/hypothetical-questions/
- ↑ https://www.mayoclinic.org/healthy-lifestyle/stress-management/in-depth/stress-relief/art-20044456
- ↑ https://leadingwithtrust.com/2011/10/09/want-to-build-trust-it-helps-to-embarrass-yourself/
- ↑ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8607910/
- ↑ https://www.huffpost.com/entry/talking-about-your-ex_n_5533210
- ↑ https://greatergood.berkeley.edu/article/item/what_playfulness_can_do_for_your_relationship
- ↑ https://www.sciencedirect.com/science/article/abs/pii/S0191886904003496
- ↑ https://extension.usu.edu/relationships/faq/creating-connections-through-cooking
- ↑ https://psycnet.apa.org/record/2007-16550-004
- ↑ https://popculture.com/lifestyle/news/21-fun-and-sexy-questions-to-ask-your-partner/
- ↑ https://matadornetwork.com/notebook/definitely-travel-partner-getting-serious/
- ↑ https://www.funlovingfamilies.com/questions-to-ask-your-significant-other/
- ↑ https://psychcentral.com/relationships/trust-and-vulnerability-in-relationships#what-does-it-look-like
- ↑ https://greatergood.berkeley.edu/article/item/what_playfulness_can_do_for_your_relationship
- ↑ https://learnthefiveelements.com/personalitytypes/
- ↑ https://www.brescia.edu/2017/06/pratfall-effect/
- ↑ https://madamewriterblog.com/2018/10/22/30-spooky-halloween-tag-questions/
- ↑ https://psychcentral.com/relationships/creative-curious-questions-to-deepen-your-connection-with-your-partner
About This Article
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. With over 10 years of professional experience, 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 200,925 times.
30 votes - 75%
Co-authors: 4
Updated: May 7, 2024
Views: 200,925
Categories: Dating
Thanks to all authors for creating a page that has been read 200,925 times.
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Co-authors: 4
Updated: May 7, 2024
Views: 200,925
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