- Why deep questions work better than we expect
- Gently personal questions to start
- Questions about values and life
- Questions about feelings and growth
- Big-picture and hypothetical questions
- Which questions suit which relationship
- How to get better answers without making it awkward
- My advice for using deep questions
- Frequently asked questions
Here are 32 deep questions to ask friends, partners, family or someone you've just met, grouped from gently personal to big-picture. They're safer to ask than they feel: research reported by the American Psychological Association found people expect deep conversations to be awkward, then enjoy them more than shallow ones.
Deep questions have a reputation for being intense, the kind of thing you'd only ask at three in the morning. In practice, a well-chosen one turns an ordinary dinner into the conversation people remember for years. The secret is pacing. You don't open with 'what are you most afraid of?'; you build up, the way the famous closeness study did, and you answer every question yourself as well.
Why deep questions work better than we expect
Two pieces of research shape how I'd use this list:
| Study | What happened | How to use it |
|---|---|---|
| Kardas, Kumar and Epley (reported by the APA) | People overestimated how awkward deep talks with strangers would be and underestimated how interested others were; after trying both, they preferred the deep conversation | Be braver than feels natural |
| Arthur and Elaine Aron, 1997 | Pairs of strangers asked each other 36 questions of increasing intimacy and developed a stronger sense of closeness; the list has been used in hundreds of studies | Build up gradually, and take turns |
The bit people miss about the Aron study is the word increasing. The questions start light and get more personal over time, and both people answer each one. Asking deep questions without sharing your own answers feels like an interview, not a connection.
Gently personal questions to start
A warm-up. These are personal without being heavy, perfect for a new friend or a first real chat.
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What's a small thing that always makes your day better?
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What were you like as a ten-year-old?
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What's a hobby you'd love to have more time for?
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Which smell takes you straight back to childhood?
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What's the best compliment you've ever received?
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What do you do when you need to recharge?
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Which place feels most like home to you?
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What's something you've done that you never thought you would?
Questions about values and life
The middle layer. These reveal what someone cares about and why.
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What does a good life look like to you?
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What's a belief you held strongly that you've since changed?
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Who has shaped the way you see the world most?
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What do you think you're here to do?
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What's something you'd stand up for even if you were the only one?
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Which decision are you most glad you made?
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What do you wish more people understood about you?
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What does being a good friend mean to you?
Questions about feelings and growth
More personal. Save these for when trust is there, and share your own answer first if it helps.
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When did you last cry, and what was it about?
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What's a fear you've never told many people?
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What's the hardest thing you've ever had to forgive?
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When have you felt most alone, and what helped?
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What part of yourself are you still learning to accept?
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What's something you're proud of that nobody else noticed?
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What would you tell your younger self about a difficult time?
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What do you need more of in your life right now?
Big-picture and hypothetical questions
Philosophical questions that are fun to argue about. Great for groups and long journeys.
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If you could know the answer to one question about your future, what would you ask?
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Would you rather be remembered for something you did or someone you helped?
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What would you do differently if no one would ever judge you?
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If you could live one day of your life again, which would it be?
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What do you think happens to our memories when we're gone?
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Is it better to be loved or understood?
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What's one thing you think the world will look back on and be ashamed of?
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If you had to describe your life as a book title, what would it be?
Which questions suit which relationship
With someone you've just met, stay in the first group and maybe dip into values. With a close friend, the feelings group is where the good conversations live. With a partner, mix values and feelings, and keep the hypotheticals for long car journeys. Family is the trickiest, because history gets in the way, so the big-picture questions are often the easiest way in; an argument about whether it's better to be loved or understood can tell you more about your dad than a direct question ever would. Whatever the relationship, read the room and stop while it still feels good.
How to get better answers without making it awkward
- Build up gradually, like the Aron study. Start with the gently personal group and work forward.
- Answer every question yourself as well. Reciprocity is what turns questions into closeness.
- Let people pass. 'You don't have to answer that one' makes everyone feel safer.
- Listen more than you talk. A follow-up like 'What was that like?' goes further than your next question.
- Pick the moment. A quiet table works; a loud bar or a hurried coffee doesn't.
If you'd like lighter ways to connect afterwards, my guide to party board games has easy picks for groups, and couples might enjoy my 2 player Switch games for a relaxed evening in.
My advice for using deep questions
Choose three questions, one from each of the first three groups, and bring them to your next dinner with someone you'd like to know better. Ask them in order, answer them yourself, and see where it goes. The research suggests you'll both enjoy it more than you expect, and you might find out something that changes how you see each other.
Frequently asked questions
What are deep questions to ask?
Questions about values, feelings, growth and big ideas, such as 'What does a good life look like to you?' or 'What's a belief you've since changed?'
Are deep questions awkward to ask?
Usually less than you'd think. Research reported by the APA found people overestimate how awkward deep conversations will be and underestimate how much they'll enjoy them.
What are the 36 questions?
A set of questions of increasing intimacy published by Arthur and Elaine Aron in 1997. Strangers who asked each other the questions developed a stronger sense of closeness.
How do you ask deep questions without being intrusive?
Build up gradually, answer the questions yourself, let people pass on any question, and choose a quiet moment.
What are deep questions to ask a friend?
Try 'Who has shaped the way you see the world most?', 'What are you proud of that nobody noticed?' or 'What do you need more of right now?'
