The short answer: the best deep conversation starters ask about what someone values, how they have changed or what they hope for, without demanding a confession. “What’s something you’ve changed your mind about in the last few years?”, “What does a really good day look like for you?” and “Who taught you the most about how to treat people?” all work because anyone can answer them at whatever depth they like. Start light, match the other person’s openness, and go one level deeper at a time.
This guide gives you 60 deep conversation starters sorted into three depth levels, then sets for new friends, groups, dates and old friends. It also covers the follow-up habit that turns a good question into a real conversation, and how to go deep without it feeling like an interview or a therapy session. It is written for the UK, Ireland and Australia, and for friendships, groups and dates alike.
- Level 1 (warm): preferences and stories. “What’s the best thing you’ve learned this year?”
- Level 2 (personal): values and choices. “What are you proudest of that nobody congratulates you for?”
- Level 3 (deep): meaning and change. “What do you think your younger self would make of you now?”
Share your own answer too. Depth is built in matched steps, not one big leap.
Why deep conversations go better than you expect
Most of us default to small talk with people we do not know well, partly because we assume the other person would find anything deeper awkward. Research suggests that assumption is often wrong. In a series of experiments published in the Journal of Personality and Social Psychology, Michael Kardas, Amit Kumar and Nicholas Epley paired people, mostly strangers, to discuss either shallow or deep questions. Both kinds of conversation felt less awkward and more enjoyable than participants predicted, and the gap was biggest for the deep ones. The American Psychological Association’s summary of the study puts it simply: people underestimate how interested others are in hearing what matters to them.
Another well-known example is the “36 questions” study by psychologist Arthur Aron and colleagues in 1997, in which pairs of strangers took turns asking gradually more personal questions and reported feeling closer afterwards. The lesson from both is the same, and it is useful for friendships as much as romance: closeness tends to grow when both people disclose a little more, step by step, and listen properly.
That does not mean diving straight into someone’s biggest regret. It means giving the conversation a chance to go somewhere. If you need lighter openers first, our guide to good conversation starters for any situation covers the warm-up.
The three depth levels
Think of depth as a dial, not a switch. The aim is to turn it up gently and only as far as the other person is happy to go.
| Level | What it asks about | When to use it | Example |
|---|---|---|---|
| 1. Warm | Stories, tastes, small experiences | Early in a first meetup, in groups | “What’s a small thing that made your year better?” |
| 2. Personal | Values, choices, what matters | Once the chat is flowing, second meetups | “What’s a belief you hold that most people around you don’t?” |
| 3. Deep | Meaning, change, fears and hopes | Good friends, long walks, late in a great conversation | “What’s something you’re still trying to forgive yourself for?” |
A simple rule: only ask a question you would be comfortable answering yourself, and be ready to go first.
Level 1: warm deep conversation starters
These feel like normal conversation but open a door. They work at a first meetup, a dinner with people you half know or a work social.
- What’s the best thing you’ve learned this year, big or small?
- What’s a small thing that made your year better?
- What did you want to be when you were ten, and how close did you get?
- What’s a place that feels like home to you, even if you’ve never lived there?
- What’s something you’re looking forward to that most people wouldn’t guess?
- Which hobby would you pick up if time and money weren’t an issue?
- What’s a book, film or song that arrived at exactly the right moment for you?
- What’s the most interesting thing about where you grew up?
- What’s a skill you’re quietly proud of?
- What does a really good day look like for you?
- Who’s someone you admire who isn’t famous?
- What’s a tradition from your family you’d want to keep?
- What’s the best advice you’ve ever ignored?
- When do you feel most like yourself?
- What’s a small risk you took that paid off?
- What’s something you’ve got really into lately?
- Which era would you visit for a week, and why?
- What’s a compliment you still remember?
- What would your friends say you’re the go-to person for?
- What’s something you’ve done recently for the first time?
Level 2: personal deep conversation starters
These ask about values and choices. Use them once you have a rhythm going, or on a second meetup with someone you clicked with.
- What’s something you’ve changed your mind about in the last few years?
- What are you proudest of that nobody really congratulates you for?
- Who taught you the most about how to treat people?
- What’s a belief you hold that most people around you don’t?
- What does friendship mean to you now, compared with when you were younger?
- What’s something you used to think was important that you’ve let go of?
- What’s a decision that changed the direction of your life?
- What kind of person do you want to be in ten years, not what job?
- What do you find easy that other people seem to find hard?
- What’s a question you wish people asked you more?
- When did you last feel really out of your depth, and what happened?
- What’s a habit that has quietly made your life better?
- What’s something you’re working on in yourself at the moment?
- What do you need more of in your life, and what less?
- Which moment in the last year would you happily relive?
- How do you recharge when you’re running on empty?
- What’s a lesson you had to learn more than once?
- What does “a good life” look like to you?
- What’s something you’re grateful for that you rarely say out loud?
- What’s a rule you live by, even if you’ve never said it?
Level 3: deep starters for when you know each other
Save these for friends you trust, long walks or the end of a conversation that is already going well. Always make it easy to pass.
- What do you think your younger self would make of you now?
- What’s something you’re still trying to forgive yourself for?
- What are you most afraid people will find out about you, if you’re happy to say?
- When have you felt most alone, and what helped?
- What’s a relationship that shaped you, for better or worse?
- What would you do differently if you knew nobody would judge you?
- What’s something you’ve never quite got over?
- What do you hope people say about you when you’re not in the room?
- What’s a dream you’ve quietly given up on, and do you miss it?
- When did you last cry, and was it a good cry?
- What part of your life feels unfinished?
- What’s something you believe that you can’t prove?
- What has been the hardest year of your life so far, and what did it teach you?
- Who do you wish you’d thanked properly?
- What scares you about the next ten years, and what excites you?
- What does home mean to you now?
- What’s the kindest thing a stranger ever did for you?
- What part of yourself are you learning to like?
- If you could have one honest conversation with anyone, who would it be?
- What’s a question you’re still trying to answer for yourself?
Deep conversation starters by situation
The same question can land very differently depending on who you are with. Here is how to pick.
With a new friend
Stay mostly in Level 1, with one or two Level 2 questions once you are both relaxed. Numbers 1, 10, 21 and 25 work particularly well. For more ideas specific to new friendships, see what to talk about with a new friend, and for a bank of more personal questions our list of deep questions to get to know someone goes further. For lighter first-meeting questions, see our list of questions to ask when meeting someone new.
In a group
Choose questions everyone can answer in a sentence or two, and go round the table: “What’s a small thing that made your year better?” or “What’s something you’ve done for the first time recently?” Avoid anything that puts one person on the spot. Keep it moving, and let people pass.
On a date
Level 1 for the first half, then a few Level 2 questions if the chat is flowing. Hold back Level 3 for later dates. Our guide to first date conversation starters has stage-by-stage ideas.
With an old friend or family
This is where Level 3 shines, because trust already exists. A long walk, a car journey or a late kitchen-table chat is the natural setting. Ask, then listen without trying to fix anything.
If you’re an introvert
Deep questions can actually suit introverts better than small talk, because they create one-to-one depth rather than group chatter. Prepare two or three questions you genuinely want answered, and see our conversation topics for introverts for low-energy ways in.
How to go deep without making it intense
A deep question asked badly feels like an interrogation. Asked well, it feels like an invitation. These habits make the difference:
- Earn it with a follow-up. The easiest route to depth is a “why” or “how did that feel” about something they have already mentioned. “You said you moved to Leeds on a whim. What made you jump?” is deeper than any list question, and it is about them.
- Go first sometimes. Share a little about yourself at the depth you are asking for. It shows you are not just collecting their secrets.
- Match, don’t outpace. If they give a light answer, stay at that level for a while. If they open up, follow their lead.
- Make passing easy. “Feel free to skip that one” takes the pressure off and makes people more likely to answer.
- Listen more than you talk. Ask one good question, then let the silence breathe. Our guide on how to avoid awkward silence explains why a pause is often a sign someone is thinking.
- Do not fix. If someone shares something hard, “That sounds tough. How are you feeling about it now?” beats advice.
- Bring it back up gently. After a heavy moment, a lighter question resets the mood: “OK, happier one. Best meal you’ve had this year?”
Setting matters too. Side-by-side activities such as walking, cooking or a long table at a small dinner make deeper conversation feel less like a spotlight. A small group plan with a handful of people who all chose to be there is often the easiest place to try it.
That is why we built MeetNow, our own app, around small plans rather than profiles. A host posts a plan at a public place, such as a dinner or drinks, with a time and a number of seats. People ask to join with a short note, the host picks who comes and accepted guests get a group chat before they meet.
Want to turn this into an actual plan? MeetNow is a free app for meeting people in person: a host posts a plan at a public place, says who pays (host pays, split, pay your own or free) and picks who joins. It is live on the web now, starting in Malta: open MeetNow and see the plans near you.
What to avoid
- Leading with trauma. Do not open with questions about grief, abuse, illness or past relationships. If someone shares, listen; do not dig.
- Rapid-fire lists. Reading out questions one after another feels like a quiz. One good question with real follow-ups beats ten.
- Judging the answer. “Really? That’s a weird thing to value” will close the door for the rest of the evening.
- Using depth to test people. Deep questions are for connection, not for screening someone’s worthiness.
- Ignoring signals. Short answers, looking away or changing the subject mean “not now”. Respect it.
Frequently asked questions (FAQ)
What is a good deep conversation starter?
One that invites a story about someone’s values or experiences without demanding a confession. “What’s something you changed your mind about in the last few years?” works well because anyone can answer it at whatever depth they like.
Is it weird to ask deep questions to someone you’ve just met?
Usually not, if you warm up first. Research by Kardas, Kumar and Epley found people expect deep conversations with strangers to be more awkward than they turn out to be. Start light, then go one level deeper.
How do you move from small talk to a deeper conversation?
Ask a “why” or “how did that feel” follow-up to something they have already mentioned, and share something of your own at a similar depth. Depth grows in small, matched steps.
What topics should I avoid when going deep?
Avoid pushing on trauma, health, money troubles or past relationships unless the other person brings them up. Let them choose how much to share and never press for detail.
Do deep conversation starters work in groups?
Yes, if they are open and light enough for everyone to answer, such as “What’s a small thing that made your year better?” Go round the table and keep answers short.
What if the other person gives a short answer?
Take it as a signal, not a failure. Share your own answer, then move back to lighter ground. Some people need more time before they open up.
