Buzz
Looking to get your boyfriend laughing and spark a fun, random chat? Throwing silly and outlandish questions his way is a great way to learn more about him and bring on the smiles. In fact, sharing laughs and having fun together can bring you closer! To help kickstart the laughter, we've gathered 100 hilarious questions to ask your boyfriend, from 'would you rather' scenarios to random questions that explore his interests and views.
What You Need to Know
- Start off a funny conversation with "would you rather," "this or that," or hypothetical questions.
- Get your boyfriend laughing with questions about his childhood, embarrassing moments, and his best impressions.
- Discover more about your boyfriend by asking about his favorite foods, movies, travel spots, and quirky objects.
How to Proceed
“Would you rather sing every other word you speak or shout every other word?”
Kick off a hilarious chat with a round of “would you rather.” Play “would you rather” by presenting your boyfriend with two absurd situations or dilemmas, and let him pick. Keep the conversation flowing by asking him why he chose his option. After he answers, share your choice to see how your preferences align!
- “Would you rather always have untied shoes or a zipper on your pants that’s permanently down?”
- “Would you rather never hear music again or only be able to listen to your least favorite tunes?”
- “Would you rather forget to buy one essential item or pick up 10 unnecessary things every time you shop?”
- “Would you rather be able to communicate with animals or control plants?”
“French fries or tater tots?”
Start a playful debate with “this or that” questions. Get creative with your options and mix in some unrelated choices for a quirky conversation. These questions are a great way to explore your and your boyfriend’s similarities and differences in a fun manner! Don’t worry if he’s all about french fries while you’re a tater tot fan—having different preferences is totally healthy in a relationship.
- “Beach or mountains?”
- “Dinosaurs or mythical creatures?”
- “Salty or sweet?”
- “Always cold or always hot?”
“In a zombie apocalypse, where would you go to hide?”
Throw him into an apocalyptic scenario and see his reaction. Maybe he’d escape to a remote island while you think the best plan is to shelter in a grocery store. This is a fun way to explore his response to tough situations and gives you a chance to tease him about his choices. Get creative with the scenarios by including familiar places he visits or people he interacts with.
- “You’ve won the lottery, but can only buy 5 things before having to donate the rest. What are you purchasing?”
- “You discover a time machine. Do you travel to the past or the future?”
- “You’re given a pill that will make you 50% more attractive or 50% more intelligent. Which do you choose?”
- “If you were stranded on an island and could bring only 5 items, what would they be?”
“If you were a power tool, what would you be?”
Ask a totally random question to get your boyfriend laughing. Look around you and ask him to choose an inanimate object or inquire about which body part he’d want an extra of. Some of these questions might not reveal much about him, but they can definitely lift his spirits when he's having a rough day.
- “If you could be any musical instrument, what would you be?”
- “How many geckos would it take to defeat a bear?”
- “If you could rearrange the alphabet, how would you do it?”
- “If you were a type of drinking glass, which one would you be?”
“What’s the most embarrassing thing that’s happened to you?”
Ask him an embarrassing question to make him laugh and blush. This is a lighthearted way to help him open up about his past. You’ll both grow closer and build trust as you share experiences and moments you might not share with anyone else.
- “Have you ever been caught in a lie?”
- “What’s the weirdest thing you did as a child?”
- “What’s the strangest thing I’d find in your search history?”
- “Have you ever posted something on social media or sent a text that you later regretted?”
“What’s the funniest nickname you had as a kid?”
Dig into the funny moments from his childhood. Since you might not have known your boyfriend when he was younger, this is a fun opportunity to discover what he was like. You can tease him about how much he’s changed and bond over the funny stories he shares.
- “What’s something hilarious you believed as a child that turned out to be totally wrong?”
- “Did you have a favorite toy that you just couldn’t live without as a kid? What was it?”
- “What did you dream of becoming when you grew up?”
- “Did you have an imaginary friend back then?”
- “Were you a troublemaker as a kid, or did you behave well?”
“What’s the worst date you’ve ever been on?”
Ask about the funny moments from his past relationships. If you’re still getting to know each other, this is a lighthearted way to talk about past partners, build trust, and share embarrassing stories. Make sure to share your own awkward moments too, so he knows he’s not alone in having funny experiences.
- “What’s the most awkward moment you had with a crush?”
- “What’s the cheesiest pick-up line you’ve ever used?”
- “Have you ever been stood up by someone on a date?”
- “Who was your funniest celebrity crush growing up?”
“What’s your best animal impression?”
Challenge your boyfriend's impersonation skills while having a laugh. Turn your questions into a fun game and see who can do the best impressions. This playful activity will not only get you both laughing, but will help deepen your bond and make your relationship even stronger.
- “What’s your best cartoon character impression?”
- “What’s your best celebrity impersonation?”
- “Can you act out a scene from your favorite movie?”
- “Can you dramatically read our latest text conversation?”
“If you could be any fictional movie character, who would you choose?”
Discover his favorite movies and TV shows. Understanding the types of characters and genres he enjoys can give you a glimpse into his personality. It’s also a great way to come up with thoughtful gift ideas or themed celebrations.
- “You’re stuck inside your favorite movie. What’s going to happen to you?”
- “If you could only watch one TV show every month, which one would it be?”
- “What would the title of the movie about your life be?”
- “Which cartoon character do you think most resembles you?”
“If you could only eat one type of food for the rest of your life, what would it be?”
Find out what foods your boyfriend enjoys or dislikes. Food-related questions can reveal hidden favorites, from his favorite exotic dishes to his go-to comfort snacks. Plus, you’ll discover which meals to cook together as a fun bonding experience.
- “What’s the strangest thing you’ve ever eaten?”
- “Is there a food you’d never eat, even if you were starving?”
- “If you had to give up one of your favorite foods for life, which would you pick?”
- “What’s a food you can’t stand, but everyone else seems to love?”
“If you could relive the day we first met, what pick-up line would you try on me?”
Talk about your relationship to deepen your connection. Not every conversation about your relationship needs to be serious. Fun and quirky questions about how you met can bring you closer as you both reflect on the bond you share.
- “If we could swap bodies for a day, what would you do in my shoes?”
- “What song would you say sums up our relationship?”
- “What’s your funniest memory of us together?”
- “What silly nickname would you give me?”
“Do you prefer being the big spoon or the little spoon?”
Boost your bond by laughing and connecting with playful, flirty questions. Flirty questions can spice up your relationship and communication. Feel free to ask whatever makes you both smile.
- “Who’s your celebrity crush?”
- “What’s your favorite part of my body?”
- “What’s your favorite romantic movie?”
- “What’s your idea of the perfect date?”
“If you could visit one place and never travel again, where would you go?”
Start a conversation about travel adventures and dreams. This is a wonderful way to dive into your boyfriend’s past experiences. Use his answers as inspiration to plan a trip together that will help strengthen your connection.
- “If you had to choose, would you rather live at the bottom of the ocean or on Mars?”
- “What are your top 3 dream destinations?”
- “If you could have been born in any other country, which one would you pick?”
- “What popular place do you have absolutely no interest in visiting?”
“What’s your favorite word?”
Discover his favorite quirky things. While it’s great to know your boyfriend’s go-to foods, movies, and books, asking about fun, random topics can reveal more about him. Surprise him with these unexpected questions and keep him intrigued.
- “What’s your favorite kind of tree?”
- “What’s your top cheese choice?”
- “Which sea creature do you like the most?”
- “What time of day do you love the most?”
“What’s the wildest thing you’ve ever done?”
Discover his adventurous side. Maybe he’s a thrill-seeker or has a wild past. By revealing funny and daring stories, you’re building trust and vulnerability. If he’s into adventures, plan some exciting activities 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 gone skinny dipping?”
“What’s the most pointless skill you have?”
Play a fun trivia game all about your boyfriend’s life. Ask unique questions that only he can answer to make the game more interesting. This is a great way to bond and discover quirky facts about each other while sharing a laugh.
- “What’s a fun fact about you that nobody knows?”
- “Who’s the most fascinating person you’ve ever met?”
- “What’s a memory that stands out to you?”
- “What moment always brings a smile to your face?”
“If you could control any element, which one would you choose?”
Ask about magical powers and super abilities to get a glimpse of his inner self. While magic and powers aren’t real, these kinds of questions offer a playful way to learn more about his personality through his imaginary choices.
- “If you could have any superpower, what would it be?”
- “Which psychic ability would you want to have?”
- “What would your useless superpower be?”
- “Would you rather team up with Batman or Superman?”
“Do you prefer sleeping with your door open or closed?”
Inquire about his quirky habits and routines at home. If you're spending plenty of time together or considering moving in together, it's helpful to know his little routines and oddities. He likely has charming habits that make him uniquely lovable, even if they're not perfect.
- “Do you start with washing your hair or your body?”
- “What’s your most annoying habit?”
- “Are you a morning person or do you prefer sleeping in?”
- “What are the five things you can’t live without?”
“Have you ever experienced something supernatural?”
Discover if he has any interest in the paranormal or believes in ghosts. Dive into discussions about the supernatural and mysterious subjects—this might reveal some intriguing, spooky interests he has. If he hasn’t had any ghostly experiences, you can share some spooky tales with each other instead here.
- “What’s the most bizarre conspiracy theory you believe in?”
- “Is there an urban legend you swear by?”
- “Do you believe in karma?”
- “What’s your stance on astrology?”
- “What is your rising sign?”
“What’s one thing that terrifies you?”
Ask deeper questions without getting too serious. You can ask lighthearted questions that could lead to funny responses, but which also allow him to open up more deeply if he feels like it. These types of questions help you understand him better, while keeping the conversation easy-going.
- “What’s your biggest aspiration?”
- “If you could dine with anyone, living or deceased, who would it be?”
- “What’s something you still haven’t done but would like to?”
- “What’s your top skill or talent?”
