Deep Questions to Ask
87 questions · By Dima Tretyak, creator of DeepTalk · Updated
Small talk keeps things safe, which is exactly why it gets old. A good deep question skips the weather and the weekend plans and gets to what someone actually thinks, remembers or worries about.
The questions below are grouped by theme: life and meaning, values, the past, fears, love, self-knowledge and a few thoughtful what-ifs, plus sets for friends and for someone you've just met. Some come from the DeepTalk app, and the rest were written for this page.
Deep questions about life
Big-picture questions. Give them room and don't rush to the next one.
- 1What makes a day feel well spent to you?
- 2What would you still do if nobody ever found out you did it?
- 3What do you think most people get wrong about happiness?
- 4What does "enough" look like for you, in money, success or love?
- 5If you had to sum up what you've learned so far in one sentence, what would it be?
- 6What's something you think is worth struggling for?
- 7What part of your life feels most like it's actually yours?
- 8What do you think you're here to do, if anything?
- 9What do you think happens after death?
- 10Which chapter of your life do you think about most, and why?
Questions about values and beliefs
What someone stands for usually shows up in the small rules they live by.
- 11What's a rule you live by that you've never said out loud?
- 12Where do you draw the line between being kind and being honest?
- 13What's something you'd refuse to do even for a lot of money?
- 14Whose opinion of you matters more than it should?
- 15What's a belief you hold that others might disagree with?
- 16What do you admire in other people that you're still working on yourself?
- 17What would you want a stranger to understand about you after one conversation?
- 18What does loyalty mean to you, and where does it end?
- 19What's a cause you'd give up a weekend for without thinking twice?
- 20What value from your family would you keep no matter what?
Rather play than scroll? DeepTalk deals these out one card at a time.
Questions about the past
Memories are where most of the good stories live.
- 21What's a year of your life you'd happily live again?
- 22Which moment would you revisit just to watch, not change?
- 23What's a door you closed that you're glad stayed closed?
- 24What did your younger self worry about that turned out fine?
- 25Who were you trying to impress at sixteen, and did it work?
- 26What's a decision that looked small at the time and changed everything?
- 27What's a childhood experience that shaped who you are?
- 28If you could talk to your younger self, what would you say?
- 29What's a memory you return to when you need comfort?
- 30What's something you only understood years after it happened?
Questions about fears and vulnerability
Ask these gently, and be ready to answer them yourself.
- 31What's a fear you've outgrown, and how did it happen?
- 32When did you last feel completely out of your depth?
- 33What are you most afraid people will discover about you?
- 34What do you avoid thinking about because it feels too big?
- 35What's the hardest thing for you to ask for?
- 36When do you feel most alone, even around people?
- 37What's a risk you keep circling but haven't taken yet?
- 38What part of yourself do you hide at work?
- 39What kind of criticism still gets under your skin?
- 40What helps you when your mind won't slow down at night?
Deep questions about love and relationships
For friends and partners alike. For couple-specific ones, see our questions for couples.
- 41What did your parents' relationship teach you about love?
- 42What's the difference between being loved and being understood, for you?
- 43What's a relationship that changed how you see yourself?
- 44How can you tell when someone is really listening to you?
- 45What do you need from people that you find hard to put into words?
- 46What's the kindest thing someone's done for you?
- 47Who do you miss that you're no longer in touch with?
- 48What's a friendship that ended quietly, and what do you think happened?
- 49What does it take for you to trust someone again?
- 50How has your idea of love changed since you were a teenager?
Questions about who you are
The ones people rarely get asked, and usually enjoy answering.
- 51What's a compliment you secretly agree with?
- 52What's a compliment you never know how to accept?
- 53When do you feel like your true self?
- 54What's something about you that took a long time to accept?
- 55What do you do when nobody's watching that says a lot about you?
- 56What's a habit that tells people more about you than you'd like?
- 57What emotion do you struggle with the most?
- 58How are you different from the way your friends would describe you?
- 59What would your teenage self be surprised to learn about you now?
- 60What's a question about yourself you still can't answer?
Thoughtful what-if questions
Hypotheticals that aren't silly. The answer usually says more than a direct question would.
- 61If you could know the answer to one question about your life, what would you ask?
- 62If you had to spend the next ten years in one city, which would you choose?
- 63If you could keep only three memories, which would they be?
- 64If you had a year off with money taken care of, how would you spend it?
- 65If you could relive one conversation, which one would it be?
- 66If your life were a book, what would this chapter be called?
- 67If you could master one skill overnight, what would change for you?
- 68If you knew you had five years left, what would you stop doing tomorrow?
- 69If you could swap lives with anyone for a month, what would you hope to learn?
Deep questions to ask friends
For the friend you've known forever but haven't really talked to lately. More in our questions to ask your friends.
- 70What's something you wish we talked about more?
- 71When did you feel closest to me as a friend?
- 72What's a moment you needed a friend and didn't say so?
- 73What's a part of your life you think I don't really see?
- 74How do you want our friendship to look in ten years?
- 75What's a hard truth you'd want me to tell you, even if it hurt?
- 76What do you think brought us together in the first place?
- 77What's one way I could be a better friend to you?
- 78What's something you've picked up from me without realizing it?
Deep questions for someone new
Past small talk, but not too personal too fast. Good for a first coffee or a first date, and for a crush.
- 79What's something you're excited about that has nothing to do with work?
- 80What's the most interesting thing you've learned this year?
- 81What kind of people do you tend to feel at home with?
- 82What's a small thing that tells you you'll get along with someone?
- 83What's something about where you grew up that shaped you?
- 84What's something you do that most people would find surprising about you?
- 85What's a book, film or song that changed how you saw something?
- 86Who's someone you look up to that most people haven't heard of?
- 87Who's someone you can sit in silence with without it feeling awkward?
How to use these questions
- Ask one question and really listen. A single good answer beats ten quick ones.
- Go first when a question feels heavy. Sharing your own answer makes it easier for the other person.
- Use follow-ups like "what was that like?" or "why do you think that is?" to go deeper.
- Pick the setting: a walk, a long drive or a late dinner works better than a noisy bar.
- Let people pass. A deep question should feel like an invitation, not a test.
Play them as cards instead
The Deep & Personal deck in DeepTalk has 122 questions like these, one card at a time, plus 19 other decks for couples and friends.
Frequently asked questions
What are some good deep questions to ask?
Good deep questions are specific and open-ended, like "What makes a day feel well spent to you?" or "What's a decision that looked small at the time and changed everything?" They give the other person something concrete to think about instead of an abstract topic.
What are deep questions to ask your friends?
With friends, questions about your shared history and what you don't usually say work best: "When did you feel closest to me as a friend?" or "What's something you wish we talked about more?" They turn catching up into a real conversation.
How do you ask deep questions without it being awkward?
Warm up with lighter questions, share your own answer first, and pick a relaxed setting. It also helps to say why you're asking, for example that you realized you've never talked about it.
Are these deep questions good for a first date?
Some are. The set for someone new is designed for early conversations: personal enough to be interesting, but nothing that feels like an interrogation. Save the questions about fears and the past for when you know each other better.