70 Deep Questions to Ask Friends (From Light to Properly Deep)

Good deep questions ask about experience rather than opinions, and they leave room for an answer of any size. “What's something you've changed your mind about recently?” works because a friend can answer it with a joke or with something that matters, and either is fine. Below are 70 deep questions to ask friends and people you're getting to know, grouped from light to properly deep.

The questions are the easy part. What makes them land is how you ask: one at a time, at the right moment, answering them yourself too, and following the answer rather than the list. That bit comes first.

How to ask deep questions without it feeling like an interview

The best-known research on this is Arthur Aron's 1997 study, the one behind the “36 questions” that did the rounds online. Pairs of strangers took turns asking and answering questions that escalated gradually from light to personal, and they ended up feeling noticeably closer than pairs who only made small talk. Two features did the work: the questions got deeper slowly, and both people answered every one.

More recent work points the same way. In 2022, Michael Kardas, Amit Kumar and Nicholas Epley found that people expected deep conversations with strangers to be more awkward than they turned out to be, and underestimated how interested the other person would be. Most people are more up for a real question than you think.

So, a few ground rules:

• One at a time. Two deep questions back to back is a quiz. One, then a long tangent, is a conversation.
• Answer it yourself. Ideally after they do. If they hesitate, go first to show the size of answer you mean.
• Pick the moment. Walks, long drives, cooking together, the end of a night. Side by side is easier than across a table.
• Offer an out. “You can totally pass on this one” makes people more likely to answer, not less.
• Follow the answer, not the list. The best question is usually the follow-up: “What made you change your mind?”
• Don't go deep in a big group. Eight people at dinner want the lighter end. Save the rest for one-to-one.

Light: easy questions to get things going

These are conversation starters for friends, new or old. Fine for a group, a first coffee or a quiet group chat.

1. What's the best thing that happened to you this month?
2. What's something you're looking forward to?
3. What's a small thing that's made your week better?
4. What's the last thing you got genuinely excited about?
5. What's a skill you'd learn instantly if you could?
6. What's your ideal ordinary Saturday, not a holiday?
7. What did you want to be when you were ten?
8. What's a smell or a song that takes you straight back somewhere?
9. What's something you're weirdly good at?
10. What's the best meal you've ever had, and who were you with?
11. Which year of your life would you happily do again?
12. What's something you've got into recently?

Deep questions to ask to get to know someone

Personal without being heavy. Good for someone you've met a few times and want to know properly, the stage where most friendships either deepen or stall.

1. What's something you're really into that most people don't know about?
2. What does a good day look like for you, start to finish?
3. What were you like at fifteen?
4. Who's had the biggest influence on how you turned out?
5. What's something you believed as a kid that you've had to unlearn?
6. Where do you feel most like yourself?
7. What's a decision that changed the direction of your life?
8. What do you do when you need to recharge?
9. What's something people often get wrong about you?
10. What's a compliment you've never forgotten?
11. What are you trying to get better at right now?
12. What's a place that feels like home that isn't where you live?

Middle: how you think

Questions about values and views. They tend to start debates, in the good way.

1. What's something you've changed your mind about in the last few years?
2. What's a rule you live by, even if you've never said it out loud?
3. What do you think you'll care less about in ten years?
4. What does success look like to you now, compared with five years ago?
5. What's something you'd defend even if everyone around you disagreed?
6. What's a piece of advice you ignored and later wished you hadn't?
7. What's the kindest thing a stranger has ever done for you?
8. Which do you value more: being understood or being liked?
9. What's something you're proud of that you rarely mention?
10. If you had a year off with money taken care of, what would you actually do with it?
11. What makes you trust someone?
12. What do you think most people are quietly worried about?

Deep questions to ask friends

These are for people you already know and trust, or for a late conversation that has got there by itself. Answer them yourself too, or don't ask.

1. What's something you wish people asked you about more?
2. When did you last feel properly proud of yourself?
3. What's a fear you've never really said out loud?
4. What's the hardest thing you've got through that most people don't know about?
5. When do you feel loneliest?
6. What do you wish you could tell your younger self?
7. What's something you're still hoping for, even if it seems unlikely?
8. What do you find hardest to ask for?
9. Is there a version of your life you sometimes wonder about?
10. What part of yourself do you hide the most?
11. Who do you miss?
12. What would you want people to say about you when you're not in the room?
13. When did you last cry, and what about?
14. What do you need more of at the moment?

Questions for old friends

Shared history is its own subject. These work especially well when reconnecting with an old friend.

1. What do you remember about when we first met?
2. What's a moment from back then you think about more than you'd admit?
3. How do you think we've each changed since then?
4. What's something you've never told me about that time?
5. Which of our old plans do you wish we'd actually done?
6. What do you think you'd be doing now if you'd never moved?
7. Is there anything you've wanted to say about how we drifted?
8. What's the best thing that's happened to you since we last properly talked?

Questions about each other

For close friends. These are the ones that tend to stick with people for days afterwards.

1. What's something you think I don't see about myself?
2. When have I been a good friend to you, and when have I missed?
3. What's something you'd like us to do together that we never have?
4. What's your favourite memory of us?
5. Is there anything you've been wanting to tell me?
6. How can I be a better friend to you right now?

Group chat and dinner table starters

Lighter, made for several people at once. Good for reviving a quiet chat.

1. What's the worst job you've ever had?
2. What's the best thing you've bought for under ten pounds?
3. Which fictional place would you actually live in?
4. What's a hill you'll die on that nobody else cares about?
5. What's your most irrational dislike?
6. What's something you've done that would surprise everyone here?

What to do with a big answer

Ask enough real questions and eventually someone gives you a real answer. This is the moment that matters, and it is easy to fumble.

• Don't fix it. Unless they ask for advice, they probably want to be heard, not helped. How to support someone who's venting covers this.
• Don't top it. “Oh, that happened to me too, but worse” turns their moment into yours.
• Thank them. “Thanks for telling me that” is simple and it lands.
• Offer something back, at the same depth. Not deeper, not shallower. Matching is how trust builds both ways.

That last point is most of what opening up to people comes down to. A deep question is an invitation; the real connection happens when both people accept it.

One small Spillr note: if you write Scrolls, the app's one-letter-a-day-to-a-stranger feature, a question from the middle of this list makes a very good first line. Strangers tend to answer honestly when they have nothing to protect.