Deep Questions to Ask Anyone: A Practical Guide

Why deeper questions work better than you'd expect

Most of us hover in the shallows. We ask what someone does for a living, comment on the weather, and quietly wonder why we feel a little lonely in a room full of people. The instinct is understandable: we assume that asking something real will be awkward, intrusive, or unwelcome.

The research says otherwise. In a series of studies known as Overly shallow?, Kardas, Kumar & Epley (2022) found that people consistently overestimate how awkward a deep conversation will feel, and underestimate how connected and cared-for it will leave both people. The awkwardness, it turns out, is mostly anticipatory. Once you are in it, depth feels good. You can read more about this in our research.

There's a fitting note from everyday life, too. When Mehl et al. (2010) discreetly recorded people going about their days, the happiest among them had markedly less small talk and far more substantive conversation, a result later replicated by Milek et al. (2018). Depth isn't a risk to manage. For most of us, it's the thing we're quietly missing.

How to use these questions

The best way to deepen a conversation isn't to interrogate someone, it's to escalate gently and reciprocate honestly. This is the principle behind the famous "36 questions". In a landmark study, Aron et al. (1997) had pairs of strangers work through a series of increasingly personal prompts, taking turns to answer each one. The pairs who did this reported far greater closeness than those who simply made small talk, closeness real enough that some stayed in touch for years. You can find that study in our research as well.

So treat the sets below as a ladder, not a menu. Begin with Set I, answer your own questions as fully as you'd hope the other person would, and only climb when you both feel ready. And don't be too quick to wrap up: in Keep talking, Kardas, Schroeder & O'Brien (2022) found that conversations are usually more enjoyable the longer and deeper they run than people predict. When you sense a natural ending, there's often more warmth waiting just past it.

Set I, Warm-up (curiosity, low stakes)

Gentle, open questions that invite a real answer without asking anyone to be vulnerable. They establish the rhythm of taking turns and actually listening.

• What's something small that reliably makes your day better?
• If you had a completely free afternoon tomorrow, how would you spend it?
• What's a film, book or song you'd happily recommend to a stranger?
• Where do you feel most like yourself?
• What did you want to be when you were ten, and what do you make of that now?
• What's a small skill you have that most people don't know about?
• When did you last laugh so hard it hurt, and what was it about?
• What's something you've changed your mind about in the last few years?

Set II, Going deeper (values, memory, meaning)

Once you've found an easy back-and-forth, these questions move from what someone does to who they are and what they care about. Keep reciprocating, share your own answer before, or just after, you ask.

• What's a moment you'd point to as having genuinely shaped who you are?
• Who has had the biggest influence on the way you live, and how?
• What does a good life look like to you, honestly, not the version you're supposed to say?
• What's something you're quietly proud of that rarely comes up?
• When do you feel most connected to other people?
• What's a belief you hold that you'd find hard to give up?
• Is there a version of your life you sometimes wonder about, a path not taken?
• What does friendship mean to you now, compared with when you were younger?
• When you're struggling, what actually helps, and what do people get wrong?
• What would you like to be remembered for?

The empirical backbone of "depth over small talk" is that we crave it far more than we let ourselves ask for it.

, on Kardas, Kumar & Epley (2022)

Set III, Real intimacy (trust, fear, tenderness)

Only climb here if it feels mutual and unhurried. These are the questions that, answered honestly and met with kindness, create the closeness Aron's work describes. Go slowly, and never push past a 'not yet'.

• What's something you're afraid of that you don't often admit?
• When did you last feel truly understood, and who was there?
• Is there something you wish you could tell someone in your life but haven't?
• What's a regret you've made peace with, or are still working on?
• What part of yourself are you still learning to accept?
• If you knew this conversation would stay completely private, what would you want to say out loud?
• What does being loved feel like to you, how do you know it's real?
• What's something kind you'd say to your younger self, if they could hear it?
• Of everything we've talked about, what felt most true to share?
• Having spoken like this, what's one thing you understand about me now that you didn't before?

Where these conversations can actually happen

The hardest part of a deep conversation is rarely the questions, it's finding the right person and a setting safe enough to be honest in. That's exactly the problem everconnected is built to solve: it matches two like-minded people and guides them, anonymously and one-to-one, through this same kind of escalating conversation, so the depth feels natural rather than forced. You can see how it works if you're curious.

But you don't need an app to begin. Save these questions, bring a couple to your next coffee or long walk, and answer them as openly as you'd like the other person to. The science is reassuring and the experience even more so: the conversation you're slightly nervous to start is usually the one you'll be glad you did.