Questions that go deeper than small talk (and how to ask them)

“So, what do you do?” is the question we all ask and nobody enjoys answering. It’s safe, it’s quick, and it tells you almost nothing about the person in front of you.

You don’t have to stay there. In a 2010 study, psychologist Matthias Mehl and colleagues gave 79 university students a small recorder that captured 30 seconds of sound every 12.5 minutes over four days. The team then sorted what they heard into small talk and more substantive conversation. Compared with the least happy participants, the happiest had about twice as many substantive conversations and roughly a third as much small talk.

It’s a correlation from one small study, so it can’t tell us whether deep talk makes people happier or happier people simply talk more deeply. But it’s a decent hint that the conversations worth having are the ones that go somewhere. Here’s how to get there.

What makes a question go deeper?

The best-known answer comes from a 1997 study by psychologist Arthur Aron and colleagues. They paired up people who didn’t know each other and gave them 45 minutes to work through three sets of questions, each set more personal than the last. Compared with pairs who were given small-talk questions, those pairs reported feeling closer afterwards. The list was later nicknamed “the 36 questions to fall in love”, but the study was about closeness, not romance.

The magic wasn’t in any single question. It was the pattern: going a little deeper step by step, and both people taking turns to share. One person interviewing the other doesn’t build closeness. Two people opening up a bit at a time does.

Won’t deep questions feel awkward?

Less than you think. In research published in 2022, Michael Kardas, Amit Kumar and Nicholas Epley ran 12 experiments with more than 1,800 participants, many of them talking with someone they had never met. Again and again, people expected deeper conversations to be more awkward and less enjoyable than they turned out to be. The main reason: they underestimated how interested the other person would be.

In other words, the person across from you probably wants the better conversation too. They may just be waiting for someone to ask.

20 questions to try, from light to deep

Start playful

Low stakes, a bit silly, and surprisingly revealing.

• If you woke up with a different face, would you still be you?
• If you could relive one ordinary day of your life, which day would it be?
• What if fear had no say for a week? What would you try first?
• What’s a small thing that made your week better?
• What are you into right now that would surprise people who know you?

Get curious

Still light, but now you’re learning how someone sees things.

• How old do you feel inside, and why?
• What did your younger self know that you have forgotten?
• Which small moment of your day do you love most?
• Where do you find stillness in a busy week?
• What’s something you’ve changed your mind about in the last few years?

Go deeper

Best once you’ve both laughed at least once.

• When do you feel most alive?
• What has life been teaching you lately?
• When did you last lose track of time?
• What would you keep doing even if nobody paid you?
• What’s a compliment you still think about?

The big ones

Save these for a long walk, a late train or a call with no rush.

• Who are you when nobody is watching?
• What do you know about yourself that you rarely say out loud?
• What do you think we are here to learn?
• When have you felt connected to something larger than yourself?
• What does a good life look like to you, honestly?

How to ask deep questions without it getting weird

1. Start light, then build. Open with a playful one and go deeper once you’re both relaxed. That’s the escalation from Aron’s study, in miniature.
2. Answer it yourself too. Closeness comes from both people sharing, not from one person interviewing the other. If they hesitate, go first.
3. Follow up, don’t move on. “What made you say that?” is often better than the next question on the list.
4. Let silence happen. A pause usually means someone is actually thinking. Give it a few seconds before you rescue it.
5. Offer an easy exit. “Pass if you like” keeps it a conversation, not a test.
6. Match the moment. A big question works on a long walk. In a two-minute coffee queue, maybe not.

Is small talk actually bad?

No. Small talk is the on-ramp, not the enemy. It tells you whether someone’s up for a chat and gives you both a moment to settle in. The trick is not to park there. Use it to find a thread, like a trip they mentioned or the book on their desk, then ask the question underneath. Not “where did you go?” but “what did that trip change for you?”

Let the questions come to you

If you’d like to try this with someone new, Everconnected matches you with people who share your values and interests, for one-to-one conversations by voice. It’s free to join: create an account at app.everconnected.com, or get the app from the App Store or Google Play.

Questions people ask

Sources

1. Mehl, M. R., Vazire, S., Holleran, S. E., & Clark, C. S. (2010). Eavesdropping on happiness: Well-being is related to having less small talk and more substantive conversations. Psychological Science, 21(4), 539-541. doi.org/10.1177/0956797610362675
2. Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Personality and Social Psychology Bulletin, 23(4), 363-377. doi.org/10.1177/0146167297234003
3. Kardas, M., Kumar, A., & Epley, N. (2022). Overly shallow?: Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology, 122(3), 367-398. doi.org/10.1037/pspa0000281