Funny Questions to Ask
111 questions · By Dima Tretyak, creator of DeepTalk · Updated
The funniest questions aren't jokes. They're questions that get someone to tell a story they'd normally keep to themselves, like the worst thing they've ever cooked or the most elaborate excuse they've made up to skip plans. The laugh comes from the answer.
The questions below start with ones that work on anyone, then get random, weird and a little dumb. There are rounds for friends, your partner, your crush, a guy or a girl, funny questions to ask people about you, and a set for texting.
Funny questions to ask anyone
Safe with coworkers at a party, new friends or a table of strangers. Each one asks for a small, harmless story.
- 1What's the most confidently wrong you've ever been about something?
- 2What's a rule your family had that you thought every family had?
- 3What's the weirdest task you've been given at a perfectly normal job?
- 4What's the most elaborate excuse you've made up to get out of plans?
- 5What's the most expensive mistake you've made by not reading the instructions?
- 6What did you think adults did all day when you were a kid?
- 7What's the worst thing you've ever cooked, and who had to eat it?
- 8What went wrong at the best wedding you've ever been to?
- 9What's a petty hill you're willing to die on?
- 10What's the most baffling gift you've ever had to say thank you for?
- 11What's the strangest thing you've done to avoid someone you know in public?
- 12What piece of trivia do you bring up way too often?
Random and weird questions to ask when you're bored
Random questions with no theme, for a slow afternoon, a long drive or a quiet group chat. Some answers will be strange, which is the fun part.
- 13What's the strangest thing you've found in a coat pocket?
- 14What's the weirdest pet you've ever met?
- 15What's the funniest thing you've overheard a stranger say?
- 16What's the most questionable thing you've ever put on toast?
- 17What's a dream you were sure was real for a whole morning?
- 18What conspiracy theory is funny enough that you almost want it to be true?
- 19What's the most random thing you've bought online at 2 a.m.?
- 20Which fictional character would be the worst roommate, and why?
- 21What's a sound that annoys you way more than it should?
- 22What's the oddest thing you've looked up just to settle an argument?
- 23What's something harmless you're irrationally scared of?
- 24What was your most embarrassing childhood obsession?
Rather play than scroll? DeepTalk deals these out one card at a time.
Dumb questions to ask (that are secretly great)
Stupid questions with no right answer, the kind people argue about for twenty minutes. Ask one with a straight face and see who takes it seriously.
- 25Why do we say "heads up" when we actually mean duck?
- 26Why is it called a building when it's already built?
- 27Why do we drive on a parkway and park on a driveway?
- 28How do you think the first person to milk a cow explained what they were doing?
- 29What do you think fish call water?
- 30Why isn't the word "phonetically" spelled the way it sounds?
- 31How would you argue that a hot dog is or isn't a sandwich?
- 32Why do noses run while feet smell?
- 33How many ducks would it take to carry a person, and how did you get that number?
- 34Who decided that the alphabet should go in this order?
- 35Why do we park our cars outside and keep junk in the garage?
Funny questions to ask your friends
For friends with shared history and a few stories they'd rather forget. More rounds in questions to ask your friends.
- 36What's the worst idea I've talked you into?
- 37Which of our inside jokes would make zero sense to anyone else?
- 38What do you remember about me from when we first met that I'd rather you forgot?
- 39Which argument in our group lasted way longer than it deserved?
- 40What's the dumbest plan we've ever actually gone through with?
- 41What's a photo of me you've been saving for the right moment?
- 42Which gift did I give you that you secretly hated?
- 43What's a story about me you tell people that I'd tell differently?
- 44Which night out with us do you still tell people about?
- 45Which of your relatives would win a reality show, and which show?
- 46Who in our group would you trust least with your unlocked phone, and why?
Funny questions to ask your partner
Questions about the small, odd things you've learned about each other. Good for a lazy night in. For more, see questions for couples.
- 47What's the weirdest habit of mine you've gotten used to?
- 48What did you honestly think when you first saw my place?
- 49What's the silliest thing we've bickered about for more than an hour?
- 50What's my most dramatic reaction to a tiny problem?
- 51What noise do I make in my sleep that you've never told me about?
- 52What's the worst purchase we've made together?
- 53What would my contact name be in your phone if you were being honest?
- 54Which of my friends do you secretly think is the funniest?
- 55What's the most embarrassing thing I've done in front of your family?
- 56What's something I say so often that you could do an impression of it?
- 57What song do I sing the wrong words to that you've never corrected?
Funny questions to ask your crush
Playful questions that make someone laugh and talk about themselves at the same time. They work in person or over text. More in questions to ask your crush.
- 58What's a snack you'd defend in court?
- 59What's the worst date idea you've ever heard of?
- 60How have you tried to look cool and failed spectacularly?
- 61What's your go-to karaoke song, and how good is your performance really?
- 62What's a red flag of yours that's actually just funny?
- 63What's the most over-the-top thing you've done to get a crush to notice you?
- 64What was your most awkward phase, and how long did it last?
- 65What's a compliment you got that you're still not sure was a compliment?
- 66Which cartoon character did you have a crush on as a kid?
- 67What's a dance move you're weirdly proud of?
- 68How did your strangest first date end?
Funny questions to ask a guy
Questions about dares, DIY disasters and questionable purchases. Most guys have at least one story for each.
- 69What's the dumbest thing you and your friends have done on a dare?
- 70What's the worst injury you've gotten trying to show off?
- 71What kitchen tool have you used for something it was never meant for?
- 72How long have you driven around lost before admitting you needed directions?
- 73Which sports team do you hate for reasons you can't explain?
- 74What's the most money you've spent on something you used once?
- 75What TV show would you never admit to bingeing?
- 76How far have you gone to fix something yourself instead of calling someone?
- 77What was your most questionable fashion choice in high school?
- 78What toy from your childhood would you still play with today?
- 79What nickname have your friends given you that you'd never let your mom hear?
Funny questions to ask a girl
Questions about group chats, home experiments and the movie lines she can recite. Light, a little nosy and good on a date.
- 80What's the funniest thing that's happened to you while waiting in a bathroom line?
- 81What's the most dramatic thing your group chat has ever argued about?
- 82Which celebrity do you feel weirdly protective of?
- 83What's the worst beauty or hair experiment you've tried at home?
- 84What's a hobby you picked up and dropped within a week?
- 85What's the most unhinged thing you've done for a concert ticket?
- 86What's the most awkward thing you've said to someone you admire?
- 87What movie scene have you watched so many times you can recite it?
- 88Which text from someone you were dating still makes you laugh?
- 89What's the worst outfit your mom made you wear for a photo?
- 90Which reality show would you be kicked off first, and for what?
Funny questions to ask about yourself
Turn the questions around and ask a friend or partner about you. Be ready for honesty. To see how well they really know you, try do you really know me questions.
- 91What do you think my search history looks like?
- 92Which animal do I remind you of, and why?
- 93What would my warning label say?
- 94What do you think I was like in middle school?
- 95Which sitcom character do I turn into after two drinks?
- 96Which song should play every time I walk into a room?
- 97What job do you think I'd be hilariously bad at?
- 98What would my dating profile say if you wrote it?
- 99What do strangers probably assume about me in the first five minutes?
- 100Which emoji is the most me?
Funny questions to ask over text
Questions you can answer with a screenshot, a photo or a meme. Good for reviving a quiet chat.
- 101What's the funniest autocorrect fail you've ever sent?
- 102What's the most chaotic screenshot on your phone right now?
- 103What's the weirdest voice note you've ever received?
- 104What's the oldest photo in your camera roll you'd still post?
- 105What's the last meme that made you snort?
- 106Which contact in your phone has the strangest name, and why?
- 107What's the worst thing you've accidentally liked while scrolling someone's old photos?
- 108What's the most passive-aggressive text you've ever received?
- 109What's the funniest wrong-number text you've gotten?
- 110What GIF best describes your week so far?
- 111What's the dumbest argument you've had over text?
How to use these questions
- Start with the questions for anyone. Save the ones about your partner, your crush or yourself for people who know you.
- Answer your own question first if the other person hesitates. A good story makes it easier for them.
- In a group, go around the circle with the same question and vote on the best answer.
- Throw in a dumb question when the conversation stalls. Arguing about it is the whole point.
- Over text, ask for a screenshot or a photo instead of a long answer.
- Keep it kind. Laugh with people, and skip anything that would really embarrass someone in front of others.
Play them as cards instead
DeepTalk deals questions like these one card at a time, with 20 decks and over 2,000 questions for couples and friends.
Frequently asked questions
What are some fun questions to ask?
Questions that pull out a small story: "What's the most confidently wrong you've ever been about something?", "What's a rule your family had that you thought every family had?" or "What's a petty hill you're willing to die on?" They work with almost anyone and need no setup.
What makes a question funny?
Usually the answer, not the question. Ask about mistakes, odd habits, disasters and things people only admit to with a laugh, like the worst thing they've cooked. Specific questions get funnier answers than broad ones, because they bring up a real memory.
What are some random questions to ask?
Try "What's the strangest thing you've found in a coat pocket?", "What's the most questionable thing you've ever put on toast?" or "What's the most random thing you've bought online at 2 a.m.?" Random questions are good when you're bored or a group chat has gone quiet.
What are some joke questions?
Joke questions are dumb questions that sound like they have no answer, like "Why do we drive on a parkway and park on a driveway?" or "Why is it called a building when it's already built?" Ask one with a straight face. The fun is in watching people try to answer it.
What are good funny questions for 21 Questions?
Pick ones that lead to a story, like "How have you tried to look cool and failed spectacularly?" or "What's a snack you'd defend in court?" Open with a few funny questions before the personal ones. Our [21 Questions game page](/questions/21-questions) has a full funny round.
What are funny questions to ask your friends?
Ones about your shared history: "What's the dumbest plan we've ever actually gone through with?", "Which of our inside jokes would make zero sense to anyone else?" or "What's a photo of me you've been saving for the right moment?"
Related collections
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