Deep Questions to Ask: 100 That Go Past Small Talk

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Deep questions ask what someone values, remembers and hopes for, not just what they do all day. Below are 100, grouped by theme, with advice on when to ask, how to ask and what to leave alone.

What makes a question deep rather than nosy?

A deep question asks about the why behind a person: not where they work but what they care about, not where they've been but what stayed with them.

That isn't the same as a personal question. Someone's salary, surname or reasons for a divorce are personal, and from a new contact, asking feels like prying. A deep question lets the other person decide how much to share: a line or the whole evening, and either is fine.

Before you send one, try a quick test: would you happily answer it yourself, tonight, to someone you'd been chatting to for an hour? Every question below passes, and our questions collection has lighter ones for sillier moods.

When should you go deep in a chat?

Not in your first message. A deep question from someone you've known for thirty seconds puts them on the spot, however lovely it is. Start light, with one of our icebreaker questions or something from their profile, and let the chat find its feet.

You'll feel the moment arrive. Their replies get longer, they ask things back without a nudge, and one of you mentions something real: a move, a worry, a plan they're excited about. That's your opening, and it often follows twenty minutes of nonsense about biscuits.

Pick your setting, too. Messages fly past in a busy chat room and nobody wants to pour their heart out to a crowd, so save the big ones for a private message, or a quieter room late in the evening when the pace drops.

How do you ask a deep question without it feeling heavy?

Four habits decide whether a big question opens someone up or makes them go quiet.

Go first. Answer it yourself, or offer to: "I'll tell you mine if you tell me yours." It proves you're not after anything you'd hold back yourself.
Offer an easy out. Add "pass if it's too much" or "no pressure on this one". People open up more when they know they don't have to.
One at a time. One deep question per message, and two or three in an evening at most, with lighter chat in between. Stack them up and it turns into a survey.
Then listen. Read the whole answer, respond to the part that matters most, and ask about that. Don't rush to top their story or fix their problem.

A made-up example of all four in one go:

Can I ask you a deeper one? Say pass if it's too much.
Go on, I'm intrigued.
When did you first feel like a proper grown-up? Mine was a broken boiler, on my own, in January.
Ha. Moving out and realising nobody else was going to buy the loo roll.
The loo roll moment. Did you get the hang of it quickly?
About a year. I still buy far too much, just in case.

Look at the follow-up. It picks up the funny detail rather than jumping to the next question on a list, and that's what turns one good question into a long chat. There's more on that knack in how to keep a conversation going.

Deep conversation questions that get past small talk

A bridge from "how was your day?" to something real. They're still easy to answer, but each one asks for an opinion or a reason rather than a fact.

You've told me what you do all day. What do you actually care about?
When someone asks how you are, you probably say fine. What's the longer answer?
What's been taking up most of your headspace this week?
What's the last thing that made you stop and think?
If you had to give a talk tomorrow with no notes, what would it be about?
What's an opinion of yours that takes a few minutes to explain properly?
What's a small habit of yours that says a lot about you?
What's the part of your work that nobody outside it really understands?
What's something you only talk about once you know someone well?
What's the most honest answer you could give to "what do you do for fun?"
What would we talk about if work, weather and the news were banned?
What are you curious about at the moment, for no practical reason?

Deep questions about memories and growing up

Where someone comes from explains a lot about who they are now. Keep these warm rather than probing, and remember that not everyone had an easy start: if they steer away from family, follow their lead.

What did a Sunday sound like in the house you grew up in?
When did you first feel like a proper grown-up, and were you right?
What's a memory that's much funnier now than it was at the time?
What's an ordinary day from years ago that you remember for no obvious reason?
Who outside your family believed in you before you believed in yourself?
What did you get told off for most when you were younger?
What scared you growing up that seems daft now?
What's the first thing you ever saved up for, and was it worth the wait?
Which place from your past would you walk round again, just for an hour?
Which song still drops you into one particular summer?
Who in your family are you most like, and when did you first notice?
What's a story your family tells about you that you can't remember happening?
What did you assume grown-ups had worked out, until you became one?

Deep questions about values and beliefs

These get to what someone stands for. Ask with curiosity rather than as a test, and be ready for an answer you don't share: you're getting to know them, not refereeing a debate.

What do you think we owe people we'll never meet again, like the person behind you in a queue?
What's a small rule you live by that nobody ever taught you?
What does being a good person look like on an ordinary Tuesday?
When is a white lie the kind thing to tell?
How much of where you are now is down to luck, do you reckon?
Which compliment about your character would mean more to you than any about your looks?
Which of your values came from your family, and which did you choose for yourself?
What's something worth getting properly cross about?
What do you notice about how people treat someone who can't do anything for them?
How do you decide who gets a second chance?
Do you think people really change, or do they just get better at hiding things?
Who do you ask before a big decision, and do you actually take their advice?
What's a habit you admire in other people but can't seem to manage yourself?

Deep questions about dreams and the future

Hopes are lovely to talk about because nothing has gone wrong with them yet. A five-year plan or a daydream on the bus, they tell you what someone is reaching for.

What does an ordinary Wednesday look like in the life you're hoping for?
What would you like to be properly good at in ten years, if you started now?
If the next five years went really well, what would be different?
What's something you hope you never stop doing, however busy life gets?
What's a plan that makes you nervous in a good way?
What would you love to build, make or start from scratch?
What do you hope stays exactly as it is in your life?
What's the next big change you can feel coming?
What's a skill you'd like to teach someone else eventually?
When you picture yourself happy a few years from now, who's around you?
What's something you hope you'll care a lot less about one day?
What's a subject you'd love to properly get your head round?

Deep questions to ask a friend

For a friend you've known for years, or one you've made in the chat rooms. They're often easier to ask than questions about love, and the answers show how someone treats the people closest to them.

When did you know we were going to be proper friends?
What do you need from a friend when things go wrong: advice, distraction or just company?
What's the most useful thing a friend has told you that you didn't want to hear?
Which of your friends knows a version of you nobody else sees?
Have you ever outgrown a friend, and how did you know?
What kind of friend are you in a crisis: the planner, the joker or the one putting the kettle on?
What would someone have to do to earn a spare key to your place?
How do you make new friends as an adult, and is it harder than it used to be?
What can a good friend say to you that nobody else could get away with?
Are you the friend who keeps in touch, or the one who gets kept in touch with?
What's something we've never talked about that you think we should?
What's the most "us" memory we've got so far?

Deep questions to ask your partner

For a partner, or someone you're starting to fall for. Every one is clean, and none needs a candlelit table: they work just as well in a late message. Meeting someone for the first time? Our first date questions are a lighter place to start.

What did the relationships you saw growing up teach you about love?
What makes you feel looked after, even on a rotten day?
What's a part of you that only shows once someone has stuck around for a while?
When you're upset, do you want to be talked to, left alone or fed?
What's a tiny thing someone could do on a Monday morning that would make you feel loved?
What do you think love asks of people that nobody warns them about?
When do you feel closest to someone: talking, laughing or doing nothing together?
How do you think we've changed since we first started chatting?
What's a dream of yours you'd want a partner to cheer on?
What's something you find easy to say in a message but hard to say face to face?
What do you hope someone notices about you without being told?
Which love story, real or made up, gets it most right?
What's something you'd never want a partner to change about you?

Deep questions to get to know someone properly

These turn the spotlight on who someone is when nobody's watching. They suit a chat that has already found its rhythm, and they're better still when you answer each one too.

What do you do with yourself when nobody needs anything from you?
What's a compliment you find hard to accept?
Which feeling do you find hardest to show?
When something goes wrong, what's the first thing you tell yourself?
What's a contradiction in you that you've learned to live with?
What are you like when you're really, properly happy?
Where do you feel like a fish out of water, and do you mind?
If you met yourself at a party, would you get on?
What drains you, and what fills you back up?
What do you find yourself defending, even when it isn't your fight?
What's a good quality of yours that you'd never think to put on a profile?
How do you act when you're nervous, and could I tell over a chat?

Big what-if questions for a long, late natter

Thought experiments take the pressure off: nobody has to confess anything, yet the answers say plenty. For quicker dilemmas, the deep would you rather questions make a good warm-up.

If memories could be traded, which one would you never sell?
If you lost your memory, what would your home tell you about who you are?
If you could sit in on one ordinary day from any century, which would you pick?
If you could swap lives with anyone for a month but kept your own worries, would you still do it?
If you could know for certain whether one past decision was the right one, which would you check?
If you could be brilliant at something but nobody could ever know, what would you choose?
If you could hear what people say about you after you leave a room, would you listen?
If you had to explain what a good life is to a visitor from another planet, where would you start?
If you could feel exactly what one other person feels for a day, whose day would you choose?
If you could watch a short film of your life so far, which scene would you watch twice?
If you could slip one line of advice into every library book, what would it say?
If nobody ever saw your photos, would you still take as many?
If someone read every message you sent today, what would they guess about you?

Want a structure for an evening of these? Take turns, one each, and play it as a round of 21 questions with passes allowed.

How do you answer a deep question well?

Sooner or later one comes back your way, and a good answer keeps a chat going just as surely as a good question does.

Tell a small story, not a big statement. "Honesty matters to me" is a full stop. The time a friend told you a hard truth over a cold cup of tea is a conversation.
Take a moment. "Ooh, let me think about that one" is a perfectly good reply, and a considered answer beats a quick one.
Share as much as feels right. You can answer the spirit of a question without the private details, and nobody is owed your whole history.
Keep the identifying bits out. Tell the story of the job, not the name of the company; the street you grew up on can stay a street.
Hand it back. Finish with their turn, or ask about the part of the question they haven't answered yet.

And if it's one you'd rather not answer, say so kindly and offer another: "that's a bit much for tonight, ask me something else". Anyone worth chatting to will take that in their stride.

What shouldn't you ask someone you've just met?

Some questions are deep in the wrong way: they reach for things a new contact hasn't earned yet. Leave these until you know someone well, and let them be the one to raise them.

Old wounds: Grief, illness, a hard start in life, why a relationship fell apart. If they mention something painful, be kind, let them lead and never dig.
Money: What they earn, what they owe, what they've got put by. It's nobody's business early on, and a new contact asking about money is a warning sign in itself.
Exes, in detail: A passing mention is fine. "Why did it end?" and "what were they like?" can wait; if they want to tell you, they will.
Anything that could identify them: Their surname, exactly where they work or live, their daily routine, the gym they go to. Even asked innocently, these are the questions a scammer would ask, so don't put anyone in the awkward spot of refusing.
Anything flirty they haven't invited: Deep isn't the same as intimate. Keep it clean, and if a chat does turn flirty, let it be because you both took it there.

How do you open up without giving too much away?

Deep chats feel close, and closeness makes it easy to overshare. You can be completely honest about your feelings, hopes and past while keeping the facts that identify you to yourself.

Natter shows your username and your nearest town or city, never your real name, email or address, and that's a good line to hold in conversation too. Keep your surname, workplace, home address and daily routine out of your answers, and check any photo for clues to where you live.

Natter is strictly for adults, 18+, and the usual sense applies here as anywhere. Keep the conversation on Natter until you've met and you're sure about them; you'll get a warning if someone tries to move it to another messaging app. Never send money, gift cards or bank details, however moving the story. Blocking is instant, and you can report anyone from inside the site. Our chat safety guide has the rest.

If someone tells you something that worries you, be kind, don't try to be their counsellor, and gently suggest they talk to someone they trust, their doctor or a local support line. If anyone is in immediate danger, that's a job for emergency services.

What people ask about deep questions

What is a deep question?

A deep question asks about the why behind someone: what they value, remember, hope for or have learned, rather than what they do or where they've been. It's open, it takes a moment's thought, and it's one the asker would happily answer too.

When should you ask deep questions in a chat?

After some easy back and forth, once the replies are getting longer and the other person is asking things back. A first message is too soon and a busy room is the wrong place, so save them for a private chat where you both have time.

What are good deep questions to ask someone you've just met?

Gentle ones that look forward or inward without prying, such as what they'd love to be properly good at one day or what they care about beyond work. Money, old hurts, exes and anything that could identify them can wait until you know each other much better.

What if someone doesn't want to answer?

Let it go straight away and offer something lighter. A pass isn't a rejection, and pushing for an answer is the quickest way to end a good chat. If someone keeps pushing you, you can block them instantly or report them from inside the site.

Can you ask deep questions on a first date?

One or two, once the nerves have settled and the conversation is flowing. Lighter questions do most of the work on a first meeting, and our first date questions have plenty of those.

How many deep questions should you ask in one chat?

Two or three in an evening is plenty, one at a time, with lighter chat in between. A string of big questions in a row starts to feel like an interview rather than a natter.

Small Talk Done? Pull Up a Chair

Make a profile, warm up with something light and save your favourite question for someone who's in the mood for a proper natter.

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