50 Funny Questions to Start a Conversation (2023)

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Believe it or not, you can learn a lot about someone after asking one simple question. Questions are a gateway to further conversation —one question often leads to another as the conversation builds and develops. Instead of taking the normal route of asking about someone’s job, hometown or college, try to kickstart your conversation with one of these funny questions! Fun questions can keep the mood light, relaxed and help the conversation to easily carry on.

Improvise with Imagination

Let your mind roam and ask some outrageous questions that let you get a look at the thoughts living in someone else’s mind. Whether you are wondering about a fictional superpower or a hypothetical situation, the possibilities are endless!

1. What superpower do you wish you always had? Let’s be honest, we’ve all had some sort of childhood fantasy that we dreamed about coming true. Will they choose a classic power like invisibility or super strength, or a superhero power like Thor or Wonder Woman?
2. What secret conspiracy theory do you think might be true? Allow creativity and jokes to take hold and see what someone’s mind can conjure up. Maybe Bigfoot or aliens are real – see what funny answers are given.
3. If you were immortal for a day, what would you do? Learn what someone would choose to do if the limitations of death did not apply. Skydiving and venturing to the bottom of the ocean are both great options.
4. If you had to be a Disney character, who would you choose? It’s fun to learn how a person sees themselves in the world of Disney. Will they be a prince or princess, villain or classic Disney character?
5. If you got three wishes from a genie, what would they be? Winning the lottery, ending world hunger, and endless wishes? Find out what someone will do when they have infinite possibilities at their fingertips!
6. How long would you last in a Zombie apocalypse? This is a great question to get a read on someone’s survival instincts. If they think they can survive, you may want to stick close to them if you ever start seeing dead people come back to life.
7. If you could talk in your sleep, what would you say? You will most likely reveal what people really say in their sleep or hear what they dream about. Either way, it’s valuable information.
8. If you had an intro song that played every time you walked into a room, what would it be? With this question, you’ll get a read on what type of music best describes their personality or what song gets them pumped up. Who will be the hip hop to your rock n’ roll?
9. If you could travel back in time to any point in history, what would it be? Do they want to see the Declaration of Independence signed in 1776? Or dance all night at a disco in the 1970’s?
10. If you had to change your name, what would your new name be? Find out an individual’s alter ego from the name they would choose. A person can also opt to keep their name the same, showing a sign of self-acceptance and appreciation.

Fancy the Future

Understand how someone envisions their future through the filter of silly questions. Keep in mind, while these questions may be humorous, a person’s answers can uncover what they are truly looking for in the upcoming years.

11. What reality show would you appear on? Get a glimpse at which reality show best defines their personality. Does their future hold a lot of baking, or the chance to gossip with the neighbors?
12. If a movie was made of your life, what genre would it be and who would play you? This question will help you understand how a person interprets their own life, but as they describe it through a movie genre and actor.
13. If money did not exist and you could have any job in the world, what would you do? Realistically, the concept of money will always be around, but you can uncover a great deal about what someone is truly passionate about.
14. Would you like a world with magic in it? We highly encourage everyone to consider a world like Harry Potter (minus He Who Shall Not Be Named and Death Eaters, of course).
15. If you could live on Mars, what would you do? Discover what someone would do in a situation that is quite literally out-of-this-world. The future may hold this opportunity sooner, rather than later!
16. What would you do with your “15 minutes” of fame? There are so many possible ways to capitalize on a moment to shine when you have the attention of the world. Find out if the person would seek fame and what they would do, or if they would shun the limelight entirely.
17. If you could travel anywhere in the world, where would you go? A romantic getaway to Paris, an exciting trip to Las Vegas, or a relaxing vacation to Cancun can be indicators of various personality traits and help you learn what means most to them.
18. What celebrity do you wish you would run into walking around town? Learn who someone idolizes and wishes they could meet outside of their television. Go further and ask them what their first question would be for the celebrity and whether they would ask for a selfie.
19. What business pitch would you make if you were on Shark Tank? There have been some crazy ideas presented on this TV show, so no pitch is out-of-bounds. Robot Drive Suits and Wired Waffles are a few of our favorites that didn’t quite bait the sharks.
20. If you could pass one talent on to your children, what would it be? Find out if a person has a secret talent that may be in store for future generations.

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Food for Thought

Connect with someone over a topic that everyone loves to discuss. Bonding over food is an easy way to become acquainted with someone and figure out your next dining spot.

21. What food represents your personality? This question can reveal a great deal about how someone views themselves. Are they spicy, sweet or salty? Comfort food or healthy cuisine?
22. What is your favorite restaurant? This question tells you a lot about a person’s food preferences. It’s also a fun way to learn about some good eating spots in your area.
23. What is the strangest thing you’ve ever eaten? Discover if someone is a risk-taker when it comes to food. Accidental or unaware consumption also counts and can lead to a great story.
24. What is the best meal you’ve ever eaten? This question may bring up stories about travel or memories of gathering around the table with family. Suggest a top three list if the person can’t decide on a clear favorite meal.
25. What food do you avoid at all costs? Whether someone has a personal vendetta against a food item or has severe allergies, you’ll learn what dish or snack to stay away from the next time you see them.
26. If you could be any flavor of ice cream, what would you be? It may be surprising, but a cookie dough person can be very different from a strawberry person. Discussing this topic will be even sweeter over ice cream.
27. If you were competing on a cooking show, what would you make? Find out the meal or dish they would show off to the world, whether it’s a five-course gourmet feast or a favorite family recipe.
28. How do you feel about pineapple on pizza? Disclaimer: the debate over pineapple on pizza can divide even the closest of friends.
29. Do you prefer a center or corner piece of a brownie? Interpret if someone is warm and gooey on the outside, or if they have a tough exterior but sweet interior. We’d recommend discussing this over a treat to curb your sweet tooth.
30. What’s the weirdest food combination you’ve ever tried? Everyone’s tastebud wirings are different, so this is the perfect chance to see what might make them unique.

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Spill Your Secrets

It’s safe to say that everyone has awkward life experiences, so you might as well relive your cringey moments by laughing about them with others.

31. What’s the most awkward thing that ever happened to you? Have you ever tripped in public or waved back to someone you thought was waving to you, but they were waving at the person behind you? It’s likely the other person can relate, so you can bond over those embarrassing moments.
32. What famous people do you obsess over on social media? We all do it, so we might as well admit it. Revealing a social media crush can shed light on their lifestyle aspirations, fashion sense, and many other traits.
33. What is one thing you own that you wish you didn’t? Ask away to find out something that they wish would disappear. Is it old workout equipment in the basement? A car they can’t wait to replace?
34. What did you last Google? Prepare yourself for some strange and mundane answers.
35. Did you ever have an imaginary friend? Get to know the ideal friend the person created to perfectly complement them.
36. What is your guilty pleasure? Invite the other person to let you in on something they may not share with everyone. You may find that you are not as different as you thought!
37. What’s one thing you’ve never told your best friend – but will tell me? People may find it easier to disclose a secret to someone they barely know than those who know them the best.
38. What was the best reason you faked being sick? Find out what someone would risk getting in trouble for by making up a fake illness. Skipping a test? A Ferris Bueller-inspired day of fun?
39. What shows are you binge-watching? Many of us love to spend some of our free time getting hooked on a new TV show. Make sure you have your own list of favorite shows ready to discuss!
40. What song do you know word-for-word? This could be a childhood tune or a song that plays on the radio today. Either way, be prepared to ask them to prove it. How else can you confirm they know all the words?

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Would You Rather?

This topic of questions truly speaks for itself and tends to give people two choices that will both land them in uncomfortable, hypothetical situations. This can be the best way to really see how someone’s mind works.

41. Would you rather speak in rhyme or riddles for the rest of your life? We’ll chime in with our line; our rhymes would be divine, but the needed time leaves us disinclined. Riddles it is!
42. Would you rather live in the 1800s or the 3000s? Learn if someone would rather time travel to the past or get a glimpse at the future.
43. Would you rather wear only uncomfortable shoes whenever you go outside or comfortable shoes 24-hours a day? Yes, the latter does include when you sleep. Sometimes it’s difficult to put the shoe on the other foot and consider what you would do.
44. Would you rather explore the depths of the ocean or outer space? It’s their choice to explore uncharted territory. Choose between uncovering the mysterious creatures that lie in the depths of the ocean or venturing into space to explore what might live beyond the earth.
45. Would you rather be able to speed read and or run at an incredible pace? Ask them to imagine the knowledge they would gain in a short amount of time by speed reading. Or save time by moving at super speed!
46. Would you rather never be able to wear pants or never be able to wear shorts? Listen to their response to a fundamental question, disguised as a funny question, of whether the person prefers warmer or colder weather.
47. Who would you rather be able to read your thoughts, your boss or your parents? We’re uncomfortable either way, so the value is in the reasoning.
48. Would you rather have five half-sized clones of yourself or one full-sized clone of yourself? This question is especially relevant if you want to catch someone off-guard and give them a good chuckle.
49. Would you rather live without the internet or live without air conditioning and heating? Ask this question to determine if someone prefers to stay plugged into technology or deal with the temperature Mother Nature sets.
50. Would you rather be trapped in a romantic comedy with your enemies or trapped in a horror movie with your friends? Regardless of your company, it’s fun to picture running around in a Hollywood scene.

Whether you’re on a date or meeting a new friend, use one of these ideas to break the ice and let the laughs guide the natural ebb and flow of the conversation. It’s always great when you can end the day with a memorable conversation and a few more funny stories to tell!

Celine Ives is a native Charlottean who enjoys cuddling with her dog, cheering on her Carolina Tar Heels and reading a good book at the park.