120 Questions to Ask Your Friends: Fun, Deep and Totally Random

You can know someone for years and still be surprised by their answer to the right question. Good questions turn a regular hangout into the kind of conversation you’re still talking about the next day.

Here are 120 questions to ask your friends, from silly to surprisingly deep, plus a few ways to use them so they feel like a conversation rather than an interview.

Fun questions to ask your friends

1. What’s the most useless talent you have?
2. If your life had a theme song, what would it be?
3. What’s the weirdest food combination you secretly love?
4. Which fictional world would you most like to live in?
5. What’s the funniest thing that’s ever happened to you in public?
6. If you could instantly master one skill, what would it be?
7. What’s your most controversial food opinion?
8. If animals could talk, which would be the rudest?
9. What would your reality show be called?
10. What’s the worst haircut you’ve ever had?
11. If you had to eat one meal every day forever, what would it be?
12. What’s a trend you’ll never understand?
13. Which celebrity would you want to swap lives with for a day?
14. What’s the most ridiculous thing you’ve ever bought?
15. If you were a ghost, who would you haunt?
16. What’s the strangest dream you remember?
17. What’s your go-to dance move?
18. What would you do if you were invisible for a day?
19. What’s the most embarrassing song on your playlist?
20. Which household chore would you pay any amount to never do again?

Would you rather questions

1. Would you rather be able to talk to animals or speak every human language?
2. Would you rather live without music or without movies?
3. Would you rather always be too hot or always be too cold?
4. Would you rather have a rewind button or a pause button for your life?
5. Would you rather be the funniest or the smartest person in the room?
6. Would you rather explore space or the deep ocean?
7. Would you rather have unlimited free travel or unlimited free food?
8. Would you rather know how you’ll die or when you’ll die?
9. Would you rather never have to sleep or never have to eat?
10. Would you rather relive one day of your life or skip ahead ten years?
11. Would you rather have a famous parent or be famous yourself?
12. Would you rather lose all your photos or all your messages?
13. Would you rather always say what you think or never speak again?
14. Would you rather be a world-class athlete or a world-class musician?
15. Would you rather live in a treehouse or a houseboat?
16. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
17. Would you rather have a personal theme song or a personal laugh track?
18. Would you rather be stuck in a lift with your boss or your ex?
19. Would you rather only whisper or only shout for a week?
20. Would you rather give up your phone or your bed for a month?

Deep questions to ask your friends

1. What’s something you’ve changed your mind about in the last few years?
2. What’s a moment you felt really proud that nobody else saw?
3. What do you wish more people asked you about?
4. What’s the best piece of advice you’ve ever ignored?
5. When do you feel most like yourself?
6. What’s something you’re still trying to figure out?
7. What does a perfect, ordinary day look like for you?
8. What’s a fear you’ve overcome?
9. Who has influenced you the most, and do they know it?
10. What’s a belief you hold that most people around you don’t?
11. What would you do if you knew you couldn’t fail?
12. What’s a small thing that always makes your day better?
13. What do you think you’ll care less about in ten years?
14. What’s a memory you’d want to keep if you could only keep one?
15. What’s something you’re grateful for that you never say out loud?
16. Which version of yourself would you most like to meet: five years younger or five years older?
17. What’s the kindest thing a stranger has done for you?
18. What’s a goal you’ve never told anyone about?
19. How do you like to be comforted when you’re having a bad day?
20. What do you think our friendship would be like if we’d met ten years earlier?

Nostalgic questions

1. What was your favorite TV show as a kid?
2. What’s the first album or song you remember loving?
3. What toy would you buy again right now if you could?
4. What did you want to be when you grew up?
5. What’s your best memory from school?
6. Who was your first best friend, and where are they now?
7. What’s a smell that instantly takes you back to being a kid?
8. What’s the best holiday you went on as a child?
9. What were you weirdly obsessed with at age ten?
10. What’s a rule your parents had that you’ll never understand?
11. What was your first phone, and what was on it?
12. What’s the worst outfit you wore as a teenager?
13. What’s a game you played as a kid that you’d still play now?
14. What was your favorite snack after school?
15. What’s the first movie you remember seeing at the cinema?
16. What’s the best birthday you’ve ever had?
17. What was your bedroom like when you were twelve?
18. Which teacher do you still think about?
19. What’s something from your childhood that doesn’t exist anymore?
20. What did you get in trouble for most as a kid?

Hypothetical questions

1. If you could have dinner with anyone, living or dead, who would it be?
2. If you woke up with $10 million tomorrow, what’s the first thing you’d do?
3. If you could live in any decade, which would you choose?
4. If you could add one law, what would it be?
5. If you started a business tomorrow, what would it sell?
6. If you could only keep five apps on your phone, which would they be?
7. If your pet could talk, what would it complain about?
8. If you could master any instrument overnight, which would you pick?
9. If you were on a desert island, which three things would you bring?
10. If you could relive one year of your life, which would it be?
11. If you were a superhero, what would your weakness be?
12. If you could design your dream house, what’s one ridiculous feature it would have?
13. If you could be famous for one thing, what would it be?
14. If you could teleport anywhere right now, where would you go?
15. If you had to swap lives with someone in this room for a week, who would you pick?
16. If you could invent a holiday, what would it celebrate?
17. If your life were a movie, who would play you?
18. If you could ask the future one question, what would it be?
19. If you had a time machine for one trip, past or future?
20. If you could wake up with one new language, which would it be?

Questions to get to know a new friend

1. What do you do when you have nothing planned?
2. What’s something you’re looking forward to this month?
3. What’s the best thing you’ve watched or read lately?
4. Are you a planner or a go-with-the-flow person?
5. What’s your ideal weekend?
6. What’s a hobby you’ve always wanted to try?
7. What’s the best trip you’ve ever taken?
8. What’s a place you’d recommend everyone visit?
9. What’s something people often get wrong about you?
10. Are you more of a big party or a small dinner person?
11. What’s your favorite way to celebrate a win?
12. What do you love about where you live?
13. What’s a podcast, show or channel you’d recommend to anyone?
14. What’s a skill you’re proud of?
15. Coffee shop, park or sofa: where do you recharge?
16. What’s something you’re bad at but enjoy anyway?
17. What’s the best compliment you’ve ever received?
18. Morning workouts or late-night snacks?
19. What’s one thing on your bucket list?
20. What made you laugh the hardest this week?

How to ask questions without it feeling like an interview

• Answer them yourself. Share your own answer after theirs. Conversation is a trade.
• Follow up once. “Why?” or “What happened next?” gets you the story behind the answer.
• Mix the depth. Two light questions, then a deeper one, then something silly again.
• Make it a game. Pass a phone around and draw questions at random, or flip it around and guess each other’s answers. That’s where how well do you know your friends questions come in.
• Let people pass. Nobody should feel they have to answer something they’re not comfortable with.

Turn your questions into a game

If you want the questions with a bit of competition, try guessing instead of asking. In Fact Or Else, the phone picks a question about someone in the group (“Would Alex rather live in a treehouse or a houseboat?”), everyone debates, and the guesser scores a point if they get it right. You can add your own questions too, so the best ones from this list (and your group’s inside jokes) can go straight into the game.