130 Questions to Ask Your Friends: Fun, Deep and Catching Up

The best questions to ask your friends are the ones that get past "good, you?". A friend you see every week can still surprise you, and a friend you've drifted from is often one good question away from a real conversation again.

Below are 130 questions, grouped by mood: fun, catching up, deep, about your friendship, how well do you know me, memories, the future, friends who live far away, newer friends and a quick either/or round. They're short and plain, so they work in person, in a group chat or typed to someone in another country.

If you're meeting someone for the first time, start with our conversation starters for online chat. If you want to go one level deeper with a single person, see questions to get to know someone deeply. This page is for people you already call friends, or would like to.

Fun questions to ask friends

Good for a group, a long drive or a slow evening.

1. What's a food you pretend to like when other people are around?
2. If your week had a theme song, what would it be?
3. What's the most useless thing you know a lot about?
4. Which fictional world would you move to, and what job would you have there?
5. What's a trend you joined and now regret?
6. If you had to teach a class tomorrow with no preparation, what would it be about?
7. What would the title of your autobiography be right now?
8. What's the strangest thing in your bag or pocket at this moment?
9. Which app would you delete first if you could keep only three?
10. What's a small thing that annoys you far more than it should?
11. If you were a snack, which snack would you be? 12. What's the most "you" thing you did this week?
12. What would you name a pet rock, and what would its personality be?
13. Which of your habits would confuse someone from 100 years ago?
14. What's a word you always spell wrong?
15. If you got a free billboard for one day, what would you put on it?
16. What's the worst haircut you've ever had?
17. What's the best thing you've ever found by accident?
18. Which household chore would you happily do forever, and which one never?
19. If animals could talk, which one do you think would be the rudest?

Catching-up questions

For when you haven't really talked in a while.

21. What's taking up most of your head space lately?
22. What's been the best part of your week, even if it was small?
23. What's something you've started that I don't know about yet?
24. Is there anything you're waiting to hear back about?
25. What are you watching, reading or listening to that you'd recommend?
26. What's been harder than you expected lately?
27. What did you do last weekend that you'd do again?
28. Who have you met recently who made an impression on you?
29. What's a decision you're stuck on right now?
30. What's something you're looking forward to this month?
31. How are you sleeping these days, honestly?
32. What's one thing that went better than you thought it would?
33. What's changed in your routine since we last talked properly?
34. Is there something you'd like help with, even a small thing?
35. What's a win you haven't told anyone about yet?

Deep questions to ask friends

Save these for one-to-one, when the conversation is already easy. Answer them yourself as well.

36. What do you understand now that you couldn't have understood five years ago?
37. What part of your personality took you longest to accept?
38. What's a fear you've outgrown?
39. What does "home" mean to you now?
40. What's something you do that you hope people notice, but they rarely do?
41. When was the last time you changed your mind about someone?
42. What's a compliment you've never forgotten?
43. Which version of yourself do you miss?
44. What's a question you're still trying to answer about your life?
45. What would you do differently if nobody you knew could see it?
46. What does a successful life look like to you, apart from money?
47. What's something you're quietly proud of?
48. What kind of person do you want to be at 70?
49. What's a hard conversation you're glad you had?
50. When do you feel most at peace?
51. Who in your life do you think about more than they know?
52. What's a lesson you keep having to learn again?
53. What's something you'd like to forgive yourself for?
54. How do you know when you need a break?
55. What gives you energy, and what drains it?

Questions about your friendship

These can feel a bit brave to ask. That's what makes them good.

56. Do you remember the moment we became real friends, not just people who knew each other?
57. What's your favourite memory of the two of us?
58. What's something I do that always makes you laugh?
59. Is there something I've said that stuck with you?
60. What's one thing we should do together that we never have?
61. When things are bad, what helps you most: advice, distraction, or just company?
62. Is there anything I do that bothers you that you've never mentioned?
63. What do we have in common that most people wouldn't guess?
64. Was there a time you needed me and I didn't notice?
65. What's the best way for me to cheer you up after a long day?
66. Which of our inside jokes do you think will last the longest?
67. What do you value most in our friendship?
68. If we met for the first time today, do you think we'd still become friends?
69. How has our friendship changed since the start?
70. What should I know about you that I probably don't?

For what makes a friendship hold up over time, see our guide to the traits of a good friend.

"How well do you know me?" questions

Ask your friend to answer these about you. Score it if you like.

71. What's my usual order at a café?
72. What would I do with a completely free Saturday?
73. Which song would you put on to cheer me up?
74. What's the one food I'd never eat?
75. What's my most-used phrase?
76. Where would I go if I could travel anywhere tomorrow?
77. What's my worst habit?
78. What am I most likely to be late for?
79. What gift would make me happiest?
80. What do I talk about when I'm really excited?

Memories and nostalgia

81. What's a smell that takes you straight back to childhood?
82. What's a song that reminds you of one exact year?
83. What did your bedroom look like when you were twelve?
84. What's a game you used to play that nobody plays any more?
85. Which teacher do you still think about, and why?
86. What's the best day you remember from a school holiday?
87. What did you collect as a kid?
88. What's a family story that gets told every time you're together?
89. What was a rule at home growing up that you thought was unfair?
90. What's a mistake from your past that's funny now?

Dreams, plans and the future

91. What's one thing you want to learn this year?
92. Where do you see yourself living in ten years, and why there?
93. What's a trip you keep saying you'll take?
94. If you could switch careers with no risk, what would you try?
95. What's a habit you want to drop before next year?
96. What do you want an average Tuesday to look like in five years?
97. What's something small you're saving up for?
98. What's one thing you want to do before your next big birthday?
99. Which skill would make your life easier the fastest?
100. What would you start if you had a year off with pay?

Questions for a friend who lives far away

Distance makes small details matter more. Ask for the ordinary things.

101. What's the weather doing where you are right now?
102. What's a new place near you that I'd like?
103. What can you do there that you couldn't do here, or the other way round?
104. What time do you usually go to sleep these days?
105. What did you eat today? I want details.
106. What's a local habit you've picked up?
107. What's a show or song that's popular there that I've never heard of?
108. What do you miss most about where you used to live?
109. If I visited for a weekend, what would we do?
110. What should we both watch or read this week so we can talk about it?

If your friend is several hours ahead or behind, our time zone overlap tool shows when you're both awake.

Questions for a newer friend

For someone you like and want to know better, without jumping straight to the deep end.

111. What's something you're into that you could explain in one minute?
112. What's your idea of a perfect lazy day?
113. Which of your friends knows you best, and why?
114. What do you do to relax after a busy week?
115. What's a hobby you dropped but want to restart?
116. What's the first place in your town you'd take a visitor?
117. What kind of humour makes you laugh hardest?
118. What do you like most about the work or study you do?
119. Are you more of a planner or a "let's see what happens" person?
120. What's something you'd like to try but haven't found anyone to try it with?

Quick either/or round

Fast, easy, and a good way to restart a chat that has gone quiet. Ask "why?" after each one.

121. Sunrise or sunset?
122. Big party or small dinner?
123. Window seat or aisle?
124. Call or text?
125. Mountains or a city break?
126. Sweet or salty?
127. Plan the trip, or just turn up?
128. Books or films?
129. Cook at home or eat out?
130. Old favourite or something new?

How to ask your friends questions (without it feeling like a quiz)

• One question, then listen. Don't read three in a row. The answer is the point, not the list.
• Answer it too. Share your own version after they reply. That turns a question into a conversation.
• Follow the interesting word. If they mention a trip, a new colleague or a bad week, ask about that before you go back to the list. Our guide on how to keep a conversation going has more on this.
• Match the setting. Fun and either/or questions suit a group. Deep and friendship questions belong one-to-one.
• Let them pass. "You don't have to answer that" makes people more likely to answer.

Over text, send one question per message, keep it short, and don't expect an instant reply. A question like "What did you eat today?" is easy to answer from anywhere, at any time.

Want more? Try our hypothetical questions for what-if fun, hot seat questions for a group game, or philosophy questions for a slow, thoughtful evening.

Try them on someone new

Questions are also how new friendships start. If your usual friends are busy, Olu matches you, in one tap, with a real person who is online now in another country. It's text only, every message is translated both ways, and it runs in your browser with nothing to install. If nobody is free, you may meet an AI local, always labelled as AI. It's free and for adults 18 and over.

Pick a question from the fun or newer-friend list and try it on someone in another country right now. For staying safe while you chat with people you've just met, read our random text chat safety tips.