Run Game Conversation

Deep conversation: how to build a real connection

6 min read

Most conversations with someone new stay at the surface because both people are waiting for the other to go first. The research on this is fairly encouraging: when strangers are asked to go deeper, the conversation tends to feel less awkward and more connecting than they predicted. What helps is a way to get there gradually, so it never feels like a leap.

What the research says (and doesn't)

In a set of studies led by Michael Kardas, Amit Kumar and Nicholas Epley, published in the Journal of Personality and Social Psychology in 2021, pairs of mostly strangers discussed either shallow or deep questions. According to the American Psychological Association's summary, the work covered 12 experiments with more than 1,800 participants. Shallow questions were things like what you think of the weather. Deep ones were more personal, such as describing a time you cried in front of another person.

Before talking, participants predicted how awkward, connected and enjoyable it would be, then rated the real thing. Both kinds of conversation went better than expected, and the gap was larger for deep ones. People also underestimated how interested their partners would be in hearing about them.

Limits worth knowing: the summary doesn't describe participant demographics or how long the conversations lasted, these were structured lab tasks with assigned questions in many cases, and a first date has other things going on (attraction, nerves, a shared bill). It says deep conversation is less risky than people assume. It doesn't say everyone wants it at every moment.

The "36 questions" study, described exactly

You've probably seen the "36 questions" list. It comes from a 1997 paper by Arthur Aron, Elaine Aron and colleagues in Personality and Social Psychology Bulletin. In the first study, pairs of strangers spent 45 minutes on tasks that gradually escalated in how personal they were. Afterward they reported more closeness than pairs who did comparable small-talk tasks. The authors called the results preliminary.

The paper was about creating closeness between strangers in a lab. The idea that the questions make people fall in love comes from a 2015 newspaper column, not the study. What the study does support is the structure: start easy, escalate slowly, and take turns.

A three-step ladder

Think of conversation in three rungs. You don't need to climb all of them in one sitting.

Facts. Where they're from, what a day looks like, what they do on weekends. Low risk, easy to answer.

Opinions. What they think about something. "Is it better to live somewhere you love or a job you love?" or "What's a thing you used to hate and now like?" These show how someone thinks without asking them to reveal much.

Feelings and meaning. What matters to them, what they're proud of, what was hard. "What's something you've changed your mind about in the last few years?" or "What were you like at sixteen?"

Move up when the current rung feels comfortable. A signal is that answers get longer, they ask you things back, or they add a story you didn't ask for. If answers are staying short, stay where you are for a while. Lighter talk is not a failure.

Pace it

A common mistake is jumping to the third rung in minute three. A question like "What's your biggest regret?" asked cold feels like a test, not an invitation.

A rule of thumb: for every step up, stay on that rung for a few exchanges. Ask a question, follow up on the answer, share something of your own, and then see where they take it. The conversation often goes deeper without a formal "deep question" at all, because a follow-up like "What was that like?" does the job, as long as you're listening well enough to mean it.

Conversation threading covers how to build from what someone just said, which is usually the smoothest way up the ladder.

Share your own, in proportion

Depth is mutual. If you ask a feeling question and offer nothing back, it feels like an interview. If you answer first with something real and brief, you set the level and give them an easy way to match it.

Match the size of what they shared. If they mention in one line that moving was hard, you don't need a ten-minute story about your own. A sentence or two, then a question back, keeps it even. (Acknowledging how they felt before you add your own is a small piece of empathy in dating.)

Choose things you're comfortable having said. Real doesn't mean everything. You can share a view, a funny failure or something you're working on without handing over your whole history.

Ask whether they want to go there

Not everyone wants depth at every moment, and the reasons are ordinary: they're tired, they're in a rush, they're at a loud bar, or they're more reserved with people they just met. You can ask without making it a big moment.

A relaxed no ("eh, long story") is an answer. Take it, say "fair enough," and shift topics. If they open up, that's an invitation, not a requirement to keep going.

Setting matters too. A common view is that depth comes easier somewhere quiet, sitting side by side or across a small table, than in the middle of a crowd. Some people say they open up more while walking or doing something together.

Questions to keep handy

These are written for a first or second meeting and sit in the middle of the ladder:

For more date-specific lists, see first date questions and talking stage questions. Telling a short story of your own also helps depth along, and storytelling in conversation shows how.

One caution on length

In a follow-up set of experiments, Kardas, Schroeder and O'Brien (2022) found that people predicted conversations would get less enjoyable over time, yet enjoyment stayed high or improved as strangers kept talking. Participants were mostly university-aged volunteers in a lab, so it may not carry over to every setting. Still, it's a reason not to end a conversation early out of a worry that you've run out of things to say.

If you use Run Game sessions for your outings, a session note about which questions led somewhere is a handy record for next time.

What to do next

  1. In your next conversation, ask one opinion question ("What's a thing you used to hate and now like?") and then follow up on the answer.
  2. After someone shares something personal, answer with a sentence or two of your own before asking another question.
  3. Try one "feel free to skip this" question this week and note how people respond.
  4. Pick three questions from the list above and memorize them, so you aren't searching for one mid-conversation.
  5. Stay on each rung for at least three exchanges before moving up.
  6. When someone's answers get shorter or they change the subject, follow them there.

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