50 fun questions to ask your friends

How to use this list

1. Pick 10 questions you'd genuinely enjoy hearing your friends guess at.
2. Mix easy ones with a couple only your closest people would get — that's where the arguments start.
3. Read them out loud, or let everyone answer on their phone at the same time with a live game.

Easy icebreakers

Openers anyone can answer — good for warming up a group.

• What's the best meal you've had this year?
• What show are you watching right now?
• What's your most-used emoji, and is it accurate?
• What's a small thing that made your week better?
• What's the last photo you took on your phone?
• Coffee order — and has it ever changed?
• What's a song you can't skip when it comes on?
• Sweet or savory snacks?
• What's your favorite season and why?
• What's the best thing you've bought recently?

Fun and silly

Low stakes, high laughter — these always get the group talking.

• What's the weirdest food combination you secretly love?
• What cartoon character did you have a crush on as a kid?
• What's the most useless talent you have?
• If your life had a theme song, what would it be?
• What's the worst haircut you've ever had?
• What silly thing are you oddly competitive about?
• What's the longest you've gone without sleep, and why?
• What's a word you always spell wrong?
• What did you believe as a kid for way too long?
• What's your guilty-pleasure song?

Would you rather

Two bad options or two great ones — either way, people argue.

• Would you rather always be 10 minutes late or 20 minutes early?
• Would you rather give up your phone for a month or dessert for a year?
• Would you rather be able to fly or be invisible?
• Would you rather always say what you're thinking or never speak again?
• Would you rather have unlimited travel or unlimited great food?
• Would you rather relive the same day forever or skip ahead ten years?
• Would you rather lose all your photos or all your contacts?
• Would you rather be famous or be the best friend of someone famous?
• Would you rather only whisper or only shout?
• Would you rather win the lottery or find your dream job?

Stories and memories

The ones that turn into twenty-minute tangents — in a good way.

• What's the most trouble you got into as a kid?
• What's your most embarrassing moment that you can laugh about now?
• What's the best trip you've ever taken?
• Who was your childhood best friend, and where are they now?
• What's the weirdest job you've ever had?
• What's a moment you'd relive exactly as it happened?
• What's the kindest thing a stranger has done for you?
• What's the story your family tells about you at every gathering?
• What's the most spontaneous thing you've ever done?
• What teacher or mentor changed how you see things?

A little deeper

Save these for later in the night — they're the ones people remember.

• What are you better at now than you were five years ago?
• What's something you changed your mind about recently?
• What does a perfect ordinary day look like for you?
• What's a fear you've outgrown?
• What compliment do you still think about?
• What do you want more of in the next year?
• Who knows you best, and what would they say about you?
• What's something you're proud of but rarely mention?
• What advice would you give yourself ten years ago?
• What tradition do you want to start?