- Why it's worth asking more than 'how's things?'
- Funny questions to ask your friends
- Nostalgic questions for old friends
- Deeper questions for close friends
- Would you rather questions for friends
- Questions for friends you don't see often
- How to get better conversations with friends
- My advice for catching up with friends
- Frequently asked questions
Here are 34 questions to ask your friends, from funny ones for a group chat to deeper questions for a long walk or a late-night catch-up. Don't be shy about the deeper ones: research reported by the American Psychological Association found people consistently underestimate how much others want to hear what they really think.
Friendships can drift into autopilot. You see each other, you swap news, you talk about work, and somehow you never get round to the stuff that matters or the stuff that makes you cry laughing. These questions are a nudge out of that rut. Some are silly, some are nostalgic, and some might surprise you with how much you didn't know about someone you've known for years.
Why it's worth asking more than 'how's things?'
Two findings make a good case for better questions between friends:
| Study | What it found | What it means for friendships |
|---|---|---|
| Kardas, Kumar and Epley (reported by the APA) | People underestimated how interested others were in their deeper thoughts and overestimated the awkwardness of deep talk | Your friends probably want the deeper conversation too |
| The liking gap (Boothby and colleagues) | After a conversation, people underestimated how much the other person liked them | You're likely more appreciated than you think |
The detail I find most encouraging is that, in the APA-reported study, people who had both a shallow and a deep conversation expected to prefer the shallow one but preferred the deep one afterwards. Friends are the safest people to test that on.
Funny questions to ask your friends
Perfect for group chats, pub nights and road trips.
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What's the most embarrassing thing you've ever done in public?
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If we were in a film together, what kind of film would it be?
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What's the weirdest thing you believed as a child?
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Which of us would survive longest in a zombie apocalypse, and why not you?
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What's your most useless skill?
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If you could only eat one meal for the rest of your life, what would it be?
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What's the worst haircut you've ever had?
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What would your reality TV show be called?
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What's the strangest thing in your bag right now?
Nostalgic questions for old friends
Memory lane questions. You'll remember things very differently.
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What's your first memory of me?
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What's the funniest thing we've ever done together?
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Which trip or night out would you relive if you could?
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What did you think of me when we first met?
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What's a song that always reminds you of us?
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Which of our old in-jokes still makes you laugh?
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What's something we used to do that we should do again?
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When did you know we'd be friends for a long time?
Deeper questions for close friends
For long walks and quiet evenings. Share your answer too.
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What's something you've been worrying about lately?
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What are you most proud of from the past few years?
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What's a dream you haven't told many people about?
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Is there anything you need from me right now?
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What's a lesson life's taught you the hard way?
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Who's had the biggest influence on the person you've become?
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What does a good friendship mean to you?
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When did you last feel really happy, and what were you doing?
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What's something you'd like to change about your life?
Would you rather questions for friends
Quick dilemmas for when the conversation needs a jolt. No 'both' allowed.
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Would you rather go on holiday together to a beach or a city?
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Would you rather know all my secrets or have me know all yours?
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Would you rather relive our best night out or skip our worst one?
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Would you rather have a friend who's always early or always fun?
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Would you rather lose your phone for a week or your voice for a day?
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Would you rather we had a podcast or a band?
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Would you rather have dinner with your younger self or your older self?
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Would you rather go back to school for a day or start a new job tomorrow?
Questions for friends you don't see often
Long-distance and busy friendships need a different approach. When you only catch up every few months, 'how are you?' gets 'fine, busy, you?' and the call ends with nothing said. Try opening with something specific instead: 'What's been the best part of the last few months?' or 'What's taking up most of your headspace right now?' On a video call, a quick round of would you rather breaks the ice before you get into the real news. And for group chats that have gone quiet, dropping in one funny question is often all it takes to get everyone talking again.
How to get better conversations with friends
- Mix funny and deep. A laugh first makes the serious question feel safer.
- Answer your own question. Friendship is a two-way street.
- Follow up on the answer before moving to the next question.
- Pick the moment. Deep questions suit a walk or a quiet table, not a noisy bar.
- Remember what they told you and bring it up later. It shows you were listening.
For a relaxed night in with friends, my round-up of party board games has easy picks, and if you're cooking, my easy dinner ideas take the pressure off.
My advice for catching up with friends
Next time you meet up, bring one funny question and one deeper one. Ask the funny one early and save the deeper one for later in the evening. You'll probably learn something new, and the research suggests your friend will enjoy it more than either of you expect.
Frequently asked questions
What are good questions to ask your friends?
Mix funny questions like 'What's your most useless skill?' with deeper ones like 'What's something you've been worrying about lately?'
What are funny questions to ask friends?
Try 'If we were in a film together, what kind of film would it be?' or 'Which of us would survive longest in a zombie apocalypse?'
What are deep questions to ask a best friend?
Questions like 'What's a dream you haven't told many people about?' or 'Is there anything you need from me right now?' work well.
Do friends want deeper conversations?
Probably more than you think. Research reported by the APA found people underestimate how interested others are in their deeper thoughts.
What should I avoid asking friends?
Steer clear of questions that put someone on the spot in front of others, such as relationship troubles or health worries. Save personal topics for one-to-one moments, and let friends choose what to share.
How do I start a deeper conversation with a friend?
Start with a funny or nostalgic question, share your own answer to a deeper one, and choose a calm moment.
