30 Questions to Get to Know Someone Deeply (for Online Chat)

Small talk gets a chat through the first few minutes. Deeper questions are what make it feel like talking to a friend. This list is for text chat with someone you've met online, and it's written so each question still makes sense after translation: short, plain and open.

For openers (the first hello, the easy "where are you from" questions), see our conversation starters for online chat. This page is for what comes after.

Before you go deeper

• Wait for real answers. If replies are a few words each, stay light for a while longer.
• One question at a time. Answer it yourself first, so it feels like a conversation and not a form.
• Let them choose the depth. If they stop, change the subject or give a short answer, follow them, not your list.
• Keep it balanced. Share about yourself as much as you ask. Going deep should go both ways.

Values and beliefs

1. What's a belief you held strongly a few years ago that you've since changed your mind about?
2. What does a good day look like for you, from morning to night?
3. What matters most to you that people around you might not know?
4. What's a rule you live by, even when nobody is checking?
5. When do you feel most like yourself?

Past and family

6. What's a childhood memory you still think about?
7. Who taught you the most about how to treat people?
8. What's a family tradition you would keep forever?
9. What's a place from your childhood you can still picture clearly?
10. What did you believe about grown-ups when you were ten that turned out to be wrong?

Goals and growth

11. What are you working toward right now, and why does it matter to you? 12. What's something you've gotten unexpectedly good at?
12. Where would you like to be in five years that you aren't yet?
13. What's a skill you wish you had started learning sooner?
14. What's one small habit that has made your days better?

Challenges and pride

16. What's a hard time you got through that you're proud of?
17. When have you been most surprised by yourself?
18. What's something that scared you that you're glad you did?
19. What helps you when a week goes badly?
20. What's a mistake that taught you something useful?

Friendship and trust

21. What do you need from friends that you don't always ask for?
22. What makes you feel really understood by someone?
23. What's a kind thing someone did for you that you still remember?
24. How do you know when you can trust someone?
25. What have you learned about being a good friend?

Your world and the world

26. What's something about your country that visitors usually get wrong?
27. Is there a custom where you live that you'd want a visitor to try?
28. What do people in your town worry about most, that you don't?
29. What do you think will look completely different in twenty years?
30. What's a question nobody asks you that you'd like to answer?

How to ask, step by step

1. Share first. One line about your own answer makes it easier for them to open up.
2. Make it specific. Build the question on something they already said: "You mentioned you moved last year. What did you miss most?" is easier to answer than a fresh topic.
3. Follow one detail. Pick the most interesting word in their reply and ask about that.
4. Hand it back. After they answer, share your own version, then pause.

Keep it clear in translation

• One question per message, in short sentences.
• Skip idioms and jokes that depend on wordplay. "What's on your mind?" can come out odd; "What are you thinking about today?" is clearer.
• If a reply looks confused, ask a simpler version instead of repeating the same words.

What to skip

• Anything about their body, looks or photos.
• Money, work details and where exactly they live. Those can wait for a friendship that has built up over time, and you should never need them to talk.
• Past relationships and dating unless they bring it up. This is a friendship chat, not a dating interview.
• Questions that test or corner them, such as "Why are you really here?" or "Prove you're real."
• Heavy topics as an opener. Loss, illness and trauma are their story to tell. If they choose to share, listen first and don't push for more.

Try one now

Pick one question, change it to fit what they just said, and send it after you've shared something about yourself. If you want a place to practise, Olu is a free, one-to-one chat with people in other countries. Whether someone is free to talk at a given moment depends on who is online, so keep the list handy and be patient.

For a friendship that goes beyond the chat, read how to make friends online, not dating. For staying safe while you get to know someone, read our random text chat safety tips.