- 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.
“Would you rather sing every other word you say or yell every other word?”
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! “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?”
“French fries or tater tots?”
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. “Beach or mountains?” “Dinosaurs or mythical creatures?” “Salty or sweet?” “Always cold or always hot?”
“If you were in a zombie apocalypse, where would you hide?”
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. “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?”
“If you were a power tool, what would you be?”
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. “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?”
“What’s the most embarrassing thing that’s happened to you?”
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. “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?”
“What’s the funniest nickname you had as a kid?”
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. “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?"
“What’s the worst date you’ve ever been on?”
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. 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?”
“What’s your best animal impression?”
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. “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?”
“If you could be any fictional movie character, who would you be?”
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. 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?”
“If you could eat only one food for the rest of your life, what would it be?”
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. “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?”
“If you could re-do the day that we met, what pick up line would you use on me?”
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. “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?”
“Do you like being the big spoon or the little spoon?”
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. “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?”
“You can travel to one place and then can never travel again. Where are you going?”
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. “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?”
“What’s your favorite word?”
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. 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?”
“What’s the craziest thing you’ve ever done?”
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. 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?”
“What’s a useless skill you have?”
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. “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?”
“If you had to pick an element to control, what would it be?”
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. “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?”
“Do you sleep with your door open or closed?”
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. “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?”
“Have you ever had a supernatural experience?”
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. “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?"
“What’s something that scares you?”
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. “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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