Questions to Ask Your Friends
113 questions · By Dima Tretyak, creator of DeepTalk · Updated
Most friend groups settle into a few default topics and rotate through them forever: work, plans, the same old stories. The right question gets you past that, even with someone you've known for ten years.
The questions below go from fun and funny to deep and juicy. There are sections for best friends, new friends, questions about yourself and about relationships, and a round for the whole group on game night or a road trip.
Fun questions to ask your friends
Easy, light and good with any friend. Start here.
- 1What's the best decision you've made this year?
- 2What's an app you'd delete if you had any self-control?
- 3What's a hobby you'd quit your job for if it paid the same?
- 4What's a movie you can quote from start to finish?
- 5What's the most last-minute plan you've ever said yes to?
- 6What's a skill you're quietly working on right now?
- 7What's a guilty pleasure song you know every word to?
- 8What's the best thing you've bought for under $20?
- 9What's your dream way to spend a three-day weekend?
- 10What's a trend you followed that you're embarrassed about now?
- 11What's a place you'd go back to in a heartbeat?
- 12What's a board game you refuse to play with us anymore?
Funny questions to ask your friends
For when you want the whole table laughing. Every answer here is a story.
- 13What's the most embarrassing thing that's happened to you in public?
- 14What's the clumsiest thing you've done this year?
- 15What's the worst text you've sent to the wrong person?
- 16What's a lie you told as a kid that got way out of hand?
- 17What's the weirdest thing you've done when you thought nobody was watching?
- 18What's your most awkward date story?
- 19Which of your habits would get you kicked out of a shared apartment?
- 20What's the most chaotic thing that's happened at a family holiday?
- 21What's the worst haircut or dye job you've talked yourself into?
- 22What's a photo of you that should never see the light of day?
- 23What's the most ridiculous thing you've been scared of?
Rather play than scroll? DeepTalk deals these out one card at a time.
Deep questions to ask your friends
For one-on-one talks, late nights and long drives. More in our deep questions.
- 24What's something you're going through that you haven't told many people about?
- 25What's a belief you had five years ago that you've let go of?
- 26When was the last time you felt truly at peace?
- 27What's a part of yourself you're still learning to accept?
- 28What do you wish you'd known at sixteen?
- 29What scares you most about the next ten years?
- 30What's a decision you're proud of even though it was hard?
- 31What does home feel like to you?
- 32Who do you miss the most right now?
- 33What would you want your friends to say about you at your 80th birthday?
- 34What would make the next year better than this one?
- 35What's a moment that changed the direction of your life?
Juicy questions to ask your friends
Secrets, crushes and confessions. Only for friends who can keep a straight face and a secret.
- 36Who was your first real crush, and do you still think about them?
- 37What's the sneakiest thing you did as a teenager?
- 38What's a grudge you're still holding, even though it's silly?
- 39Which ex would you actually pick up the phone for?
- 40What's the most scandalous thing you've done on a night out?
- 41What's a red flag you ignored because the person was attractive?
- 42Which celebrity would you drop everything for?
- 43Who's a crush you've never told anyone about?
- 44What's the most dramatic thing you've done after a breakup?
- 45What's the most trouble you got into at school?
- 46What's the worst thing you've done to get someone's attention?
- 47What's a rumor about you that was somehow true?
Questions to ask your friends about yourself
Find out how your friends really see you. To test how well they know you, try our do you really know me questions.
- 48What did you think of me before we became friends?
- 49What's something I do without realizing it?
- 50What do you think I'll be doing in ten years?
- 51What song reminds you of me?
- 52What's my most annoying habit?
- 53When have I been a good friend to you?
- 54What do you think I underestimate about myself?
- 55What job do you think I'd be secretly great at?
- 56How would you describe me to someone who's never met me?
- 57What's a memory of us you always come back to?
- 58What's one thing you'd want me to do more of?
Questions to ask your best friend
For the friend who already knows everything. Almost everything.
- 59When did you know our friendship was going to last?
- 60What do you think people misunderstand about our friendship?
- 61What's something you've never told me but probably should?
- 62When have you been proud of me?
- 63Where do you see our friendship in twenty years?
- 64What's a thing we do that only makes sense to us?
- 65What's the hardest moment we've gotten through together?
- 66What's something I taught you without realizing it?
- 67If our friendship were a sitcom, what would it be called?
- 68Who introduced us, and do we owe them a thank-you?
- 69What's a promise we should make each other right now?
Questions to ask your friends about relationships
Dating, love and everything in between. Better with a drink and an honest friend.
- 70What's the best relationship advice you've ever gotten?
- 71What's your biggest dealbreaker on a first date?
- 72How do you know when you're actually falling for someone?
- 73What's a green flag you look for in a partner?
- 74What did your last relationship teach you?
- 75What's a relationship you look up to, and why?
- 76What's your love language, and do the people you date get it?
- 77What's the most thoughtful thing a partner has done for you?
- 78What would you need to know before moving in with someone?
- 79What's something you've done for love that you'd never do again?
- 80How do you want me to tell you if I don't like who you're dating?
Questions to get to know a new friend
Past the small talk but not too personal. Good for a first coffee or hangout.
- 81What does a typical week look like for you?
- 82How did you end up living here?
- 83What's your favorite way to spend a night in?
- 84What would your high school self think of you now?
- 85What's a show you could talk about for hours?
- 86What's a cause you care a lot about?
- 87What's your family like?
- 88What's something you want to do before the end of the year?
- 89What kind of friend are you when someone's having a bad week?
- 90What's the best thing you've done in this city so far?
- 91What's a hobby you'd love to have someone to do with?
Questions for a group of friends
For game night, road trips and the group chat. Everyone answers, then everyone argues. More rounds in most likely to questions.
- 92If everyone here swapped lives for a day, whose would you want?
- 93What's your go-to order at our favorite spot?
- 94Who here would you trust to plan your whole birthday?
- 95What's the best trip this group has taken, and where should we go next?
- 96What's the funniest inside joke in this group, and how did it start?
- 97What's a tradition this group should start?
- 98Which song should be our group anthem?
- 99What's the worst idea this group has ever gone along with?
- 100If we opened a business together, what would each of us do?
- 101What's something everyone here should try at least once?
- 102What's the best night out we've had, and what made it so good?
Questions about friendship
What makes a friendship work, and what breaks one. Good for a quiet talk with a close friend.
- 103What do you value most in a friendship?
- 104What's a friendship dealbreaker for you?
- 105What's the best advice a friend has ever given you?
- 106How do you handle a fight with a friend?
- 107What's something a friendship taught you the hard way?
- 108What do you do when you feel left out by your friends?
- 109What's the kindest thing a friend has said to you?
- 110How do you make time for friends when life gets busy?
- 111How do you stay connected with friends who live far away?
- 112What's the best way to make new friends as an adult?
- 113What's a friendship you wish you'd fought harder to keep?
How to use these questions
- Start with the fun or funny questions and move to the deep or juicy ones once everyone is relaxed.
- Answer your own question too. It's a conversation, not an interview.
- In a group, let everyone answer before anyone jumps in.
- Questions about yourself work best one-on-one, when your friend can be honest without an audience.
- Anything said during the juicy round stays in the room.
Play them as cards instead
The Friendship deck in DeepTalk has 97 questions like these, one card at a time, plus 19 other decks for couples and friends.
Frequently asked questions
What are good questions to ask your friends?
Open questions with a story behind them: "What's the best decision you've made this year?", "What did you think of me before we became friends?" or "What's a moment that changed the direction of your life?" Mix light and deep ones, and ask a follow-up when an answer gets interesting.
What are some deep questions to ask your friends?
Ask about change, fears and what matters to them now: "What's a belief you had five years ago that you've let go of?", "What scares you most about the next ten years?" or "What would make the next year better than this one?" Deep questions work best one-on-one, on a walk or late at night.
What are some juicy questions to ask your friends?
Questions about crushes, secrets and exes, like "Who was your first real crush, and do you still think about them?" or "What's a red flag you ignored because the person was attractive?" Keep them for close friends and let anyone skip a question.
What questions can I ask my friends about myself?
"What did you think of me before we became friends?", "What's my most annoying habit?" and "What job do you think I'd be secretly great at?" Ask one-on-one and be ready for honest answers. If you want a quiz, ask friends to guess your favorite things and score their answers.
What are funny questions to ask your best friend?
Ones that lead to a story or a roast: "What's the clumsiest thing you've done this year?", "What's the worst text you've sent to the wrong person?" or "If our friendship were a sitcom, what would it be called?"
How do you make a game out of questions for friends?
Take turns drawing a question and answering it. Anyone can pass once per round, and the group votes on the best answer. Party games like most likely to, never have I ever and two truths and a lie use the same idea. A card app like DeepTalk deals the questions for you, so nobody has to pick the next one.