100 Questions to Ask a Stranger

1. What's the best thing that happened to you this week?
2. What time is it where you are?
3. What are you up to tonight?
4. Coffee or tea?
5. What's your comfort food?
6. What's the last song you played?
7. What are you watching right now?
8. Morning person or night owl?
9. What's the weather like there?
10. What did you have for dinner?
11. What's your go-to way to relax?
12. What's a small thing that made you smile today?
13. What hobby are you into lately?
14. What's the best app on your phone?
15. Cats, dogs or neither?
16. What's the last thing you bought that was worth it?
17. Favourite season and why?
18. What's your phone wallpaper?
19. What are you looking forward to?
20. What brought you here today?

1. If you could be famous for one thing, what would it be?
2. What's your most useless talent?
3. Which fictional world would you live in?
4. What's a hill you'd die on?
5. What's the weirdest food you love?
6. Pineapple on pizza: yes or no?
7. What would your entrance song be?
8. Which animal would be the rudest if it could talk?
9. What's your karaoke song?
10. If you won a free trip tomorrow, where would you go?
11. What's the best show you've binged?
12. What trend do you not understand?
13. What would you name a boat?
14. What's your most-used emoji?
15. What's a movie you can quote by heart?
16. Which superpower would be most useful on a Monday?
17. What's the worst gift you've received?
18. What's your guilty-pleasure song?
19. If you opened a café, what would it be called?
20. Which video game would you live in?
21. What's the most overrated food?
22. What's your favourite word?
23. What would you do with an extra hour a day?
24. What's an unpopular opinion you hold?
25. Which era would you time-travel to?

1. What's something you've changed your mind about?
2. What are you most grateful for right now?
3. What's a lesson you learned the hard way?
4. What does a perfect day look like for you?
5. Who influenced you most growing up?
6. What's a goal you're quietly working on?
7. What do people often misunderstand about you?
8. What makes you feel most like yourself?
9. What's a risk you're glad you took?
10. What would you tell your younger self?
11. What does friendship mean to you?
12. What's something you wish you were better at?
13. When did you last feel proud of yourself?
14. What book or film changed how you think?
15. What are you curious about lately?
16. What scares you a little but excites you too?
17. What would you do if you knew you couldn't fail?
18. What tradition from your culture do you love?
19. What's a compliment you still remember?
20. What does success mean to you?
21. What's something small that makes life better?
22. What's a belief you hold that most people don't?
23. What's the kindest thing a stranger has done for you?
24. What are you learning right now?
25. What do you want more of in your life?

1. Explore space or the deep ocean?
2. Speak every language or play every instrument?
3. Live in a big city or a small town?
4. Know the future or change the past?
5. Never use social media again or never watch TV again?
6. Always be 10 minutes late or 20 minutes early?
7. Have a rewind button or a pause button for life?
8. Read minds or be invisible?
9. Live without music or without movies?
10. Be the funniest or the smartest person in the room?
11. Travel by train or by plane?
12. Have a personal chef or a personal driver?
13. Live in the mountains or by the beach?
14. Meet your favourite celebrity or a historical figure?
15. Have unlimited books or unlimited games?

1. What's a dish everyone should try from where you live?
2. What's a word in your language with no English equivalent?
3. What's a festival you love?
4. What do tourists get wrong about your country?
5. What's a popular song there right now?
6. What's school or work culture like where you are?
7. What's a local saying you like?
8. What's the best place to visit near you?
9. What sport is everyone into there?
10. What's a snack I've probably never heard of?
11. How do people greet each other where you are?
12. What does your country do better than anywhere else?
13. What's the funniest stereotype about your country?
14. What's a show from your country I should watch?
15. What would you show a visitor on day one?

Pick one that fits your shared interest, ask a follow-up before moving on, and share your own answer too. Deep questions land better after a few easy ones. Research suggests deep conversations with strangers go better than people expect (Chicago Booth Review).

Never ask for real names, ages of minors, addresses, schools, workplaces, phone numbers, social handles, photos or anything sexual. On TalkWithStrangers.club these break the Community Guidelines.

A great question with no follow-up dies in two messages. A simple question with a great follow-up can run for an hour. After any answer, try one of these:

• "What do you like most about that?"
• "How did you get into it?"
• "What's the best/worst part?"
• "Has that changed for you over time?"
• "What would surprise people about that?"

When the chat is dying: "Okay, random one: what's a food you'll defend to anyone?" When they seem shy: "No pressure, but what's something you're into lately?" When they're from another country: "What's something about where you live that tourists never see?" When it's late: "What's keeping you up tonight?" When you want to go deeper: "Can I ask a slightly deeper one? What's something you've changed your mind about?"

If you ask three questions in a row without sharing anything, the chat feels like an interview. A good rhythm is question, follow-up, then a short answer of your own. Researchers who study conversation find that reciprocal sharing builds closeness, and that people underestimate how much strangers enjoy deeper topics (Chicago Booth Review).

You can learn a lot about a person without asking for personal data. If someone avoids every simple question about their interests but keeps asking where you live, what school you go to or for photos, skip and report.

Keep five go-to openers in your phone notes: one fun, one deep, one about music, one about food and one about where they live. You will never stare at an empty chat box again.