40 Questions to Ask Your Friends (Fun, Deep and Anonymous-Worthy)

Good questions turn a dead group chat into a two-hour conversation. Here are 40, from silly to deep, plus kind ones that work anonymously.

Fun questions to ask your friends

1. What’s the most random thing in your camera roll?
2. If you had a theme song, what would it be?
3. What’s your go-to fast food order?
4. What would your reality show be called?
5. What’s the funniest thing that happened to you this year?
6. What app could you never delete?
7. Which celebrity would you want as a best friend?
8. What’s your most useless talent?
9. What would you do with a free day and $100?
10. What’s a food you’ll never try again?
11. Who in our group would survive a zombie movie the longest?
12. What’s your comfort show?
13. What’s the best gift you ever got?
14. If you could live in any movie, which one?
15. What’s a hill you’ll die on?

Deep questions to ask your friends

1. What’s something you’re proud of that nobody knows about?
2. What do you want to be known for?
3. What’s a moment that changed how you see things?
4. Who has had the biggest impact on you?
5. What scares you about the future?
6. What makes you feel most like yourself?
7. What’s a goal you haven’t told anyone?
8. What do you wish people asked you more?
9. What’s the best advice you’ve gotten?
10. When do you feel the most confident?
11. What’s something you changed your mind about?
12. What would you tell yourself a year ago?
13. What does a perfect day look like for you?
14. What’s a small thing that always makes your day?
15. What do you think you’ll be doing in 10 years?

Questions to ask anonymously (keep it kind)

1. What’s a compliment you wish you heard more?
2. Who do you look up to at school?
3. What song is stuck in your head right now?
4. What’s your hidden talent?
5. What’s your dream job?
6. What’s the best thing that happened to you this week?
7. What’s your favorite memory with your friends?
8. What do you love about your hometown?
9. What would you do if you knew you couldn’t fail?
10. Who would you call first with good news?

Ask anonymously, the right way

On portal.app, every page has an answering machine. You can leave a message, ask something anonymously or send a 15-second video message. Anonymous questions go only to that person, they can answer on camera, and anything unkind can be deleted or reported. Keep it kind and it’s one of the most fun parts of the app.

About portal.app

portal.app is a free iPhone app where your friends pick you. You get 4 picks a day to vote friends for positive superlatives like “best laugh” or “most likely to be famous.” They find out they got picked. Never who. You also get your own page with an answering machine, a camera-only feed with no uploads and no AI, and lists for your school, city, state and the USA. See what’s new in 2.0.

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