How to talk to strangers

My Folx dinner experience, six tips for better conversation, and the unifying power of a red leather trenchcoat

Mar 10, 2024

Find Bronwyn. Those were my instructions, handed to me on a postcard when I entered the room. I turned to face the impenetrable mass of strangers, experiencing the same overwhelming dread I always do at these kinds of events.

Someone pointed me toward the bar in the back. After seven months without alcohol, I’d almost forgotten the blessed redemption that could be found in beelining through a crowd straight for a drink. Steph at Killjoy handed me non-alcoholic sparkling wine in a champagne flute. I felt bolder already.

I’ve been trying to get better at talking to strangers, which is how I ended up at a Folx Table event with 60+ strangers this February. Folx is a dinner party series with the tagline Talk to Strangers. It’s based on the premise that people really do want to connect deeply with strangers—they just need a little help to get there.

Personally, I needed a lot of help. I have often joked that if you want to peer into my psyche, you need only look at my recent Goodreads updates. Recent choices include Sorry I’m Late, I Didn’t Want to Come: One Introvert's Year of Saying Yes by Jessica Pan and How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen by David Brooks—not to mention several podcast episodes, essays, and even the odd academic article on the topic.

You’re probably thinking: Can’t you just be normal for once, Lane? Do you have to research everything into oblivion? Why must you overcomplicate the most basic human interactions? To which I respond: No. Yes. Still working this one out with my therapist.

As is probably obvious by now, I love conducting social experiments on myself. I had done all the reading and research. Tonight at Folx, it was time to put it to the test.

Tactic 1: Ask good questions

It’s important to say that I was wearing a bright red leather trenchcoat. I chose this look partly because red is my power color but mostly because when people don’t know what to say, they can always say, “I love your all-red look.”

“I love your all-red look!” said the woman behind me. I jumped and turned around. She was smiling at me warmly, expectant.

“Thank you! I like your—” Every interesting thought I’d ever had drained from my mind in that instant. There was a long and painful pause in my reply. A tumbleweed rolled by. “—vest,” I said weakly.

She glanced down at her outfit in surprise, as if she had never heard the word vest before in her life.

According to my research, the number one most important thing in being a good conversationalist is asking good questions. In How to Know a Person, David Brooks writes,

“The crucial question is not “What happened to this person?” or “What are the items on their résumé?” Instead, we should ask: “How does this person interpret what happened? How does this person see things? How do they construct their reality?”

Vest Woman waited for me to continue. I stared at her, my face a shining moon of idiocy. Time churned on in slow motion. I tried to think of one single question that didn’t have to do with work, which was basically the only rule we’d been given for this entire event.

“So,” I asked. “What do you do for work?”

For someone attending a dinner party explicitly focused on avoiding small talk, I was already failing spectacularly.

Tactic 2: Offer conversational doorknobs

I cut my losses, bid Vest Woman goodbye, and set off to find Bronwyn. There was a group of people chatting nearby and I sidled into the circle, surreptitiously checking their nametags.

Last year, after reading this essay, I became obsessed with conversational doorknobs, the author’s term for lobbing a bold claim or confession that invites dissent, debate, and discussion. Rather than “How many siblings do you have?”, you might ask “Why do you think you and your brother turned out so differently?” or “I’ve always secretly suspected that my sister was my dad’s favorite.”

I’d begun testing them out in my daily life.

“I wouldn’t say I’m especially susceptible to cults, but I would say I have fanatical tendencies,” I said to an acquaintance over coffee.

“People who take improv too seriously are the most terrifying demographic,” I told the guy sitting next to me at Switchyards.

“When someone says they’re ‘passionate about marketing data’, I question their sanity,” I said to a new co-worker at a recent work retreat.

“Goldendoodles should be banned from Nashville city parks,” I suggested to the group of people at Folx.1

There was an awkward shifting from foot to foot. Someone cleared their throat. Then the man across from me responded indignantly, “What could you possibly have against goldendoodles?!”

As this is a subject I could speak on for several hours straight, the conversation took off from there.

In my experimentation, conversational doorknobs tend to evoke impassioned responses—especially from the deranged goldendoodle defenders—but they are certainly never boring.

Tactic 3: Be (a little) intrusive

I was feeling buoyed now. I circled the perimeter, looking for my mark.

“Hey!” hollered a different woman, from her perch on a chair in the lounge area. “I love your all-red look!” The woman introduced me to her brother, who had come with her. He had the same name as my newborn nephew, which made me instantly affectionate toward him.

“So nice to meet you both,” I said. So far I had managed to avoid asking what either of them did for work or making inflammatory remarks about godforsaken dog breeds. Off to a good start.

I hate small talk, but I’m also reluctant to ask something too personal out of fear of being intrusive or impolite. I assume strangers aren’t willing to go there—but the opposite turns out to be true. Studies show that we overestimate the awkwardness of deep talk and underestimate how open strangers are to talking to us. Brooks asked experts how often people reject these kinds of advances:

“Every expert I consulted had basically the same answer: “Almost never.” People are longing to be asked questions about who they are. ‘The human need to self-present is powerful,’ notes the psychologist Ethan Kross.”

“Have you two always been close?” I asked them, dipping my toe into deeper conversational waters. A beat.

“No, not always,” the brother answered, smiling at his sister. “We’re ten years apart. But after I got sober and moved to Nashville, it was so helpful to be near family. Now we’re really tight.”

Safely out of the shallows, we discussed the richness of sibling relationships, the experience of getting sober and the things you learn about yourself along the way, and what it’s like to make friends in Nashville when you’re not drinking.

People (👋) love to talk about themselves. We just don’t get the opportunity very often. Being a little intrusive, then, is actually an act of generosity.

And anyway, what did being polite ever get me? This quote from Jessica Pan’s Sorry I’m Late, I Didn’t Want to Come sums it up nicely:

“The fear of being intrusive is vastly inflated. The fear of being boring and dying, having never connected with anyone, is vastly underestimated.”

Tactic 4: Go off-script

During the sit-down portion of the evening, conversation became much easier because Folx provided the questions. The Folx crew rang their cowbells and we all found our assigned tables. We were given prompt cards to steer us directly into the conversational deep end.

The woman across from me drew the first card: “What age are you? What age do you feel you are?” The woman next to me got, “What is the no, or refusal, you keep postponing?” My question, “Can you be yourself where you are and still fit in?”, felt especially relevant given my current lifestyle.

I think of conversation as having two modes: “on-script” or “off-script” (h/t Maybe Baby). On-script conversations consist of questions you could predict before they’re even asked and answers you can recite without any thought. Off-script conversations happen in that magical moment when the questions and answers break away from the script and begin to surprise you, requiring you to think and engage in real time. Brooks describes it this way:

“A good conversation is an act of joint exploration. Somebody floats a half-formed idea. Somebody else seizes on the nub of the idea, plays with it, offers her own perspective based on her own memories, and floats it back so the other person can respond. A good conversation sparks you to have thoughts you never had before. A good conversation starts in one place and ends up in another.”

At Folx, our conversation went off-script. These were not the types of questions we were used to being asked, so we had to work out the answers in real-time, together—an act of genuine vulnerability and trust among strangers. Someone would give an initial response, still a little half-baked, and the rest of us would help her probe deeper, asking questions and sharing perspectives to help shape and solidify the idea. As we answered, we learned new things about each other and ourselves.

Isn’t that the miracle of good conversation? It helps us excavate parts of ourselves that we didn’t know before. A thoughtful question from a new person can crack open my understanding of myself, my experiences, and the world around me.

When viewed this way, we see talking to strangers not as a rote exchange to be tolerated, but as a deeply creative, collaborative, and generative act.

As the folks at Folx put it:

“Talking to strangers shouldn't just happen at dinner parties or cocktail hour. It's a new posture toward connection in your life, wherever you are in the world.”

By the end of the night, I had been added to an Instagram group message with several Gen Z women—a surer sign of successful bonding than any other metric I can think of.

Tactic 5: Wear a red trenchcoat

I circled the refreshment table again, about to give up on ever finding Bronwyn.

It was tight quarters and I squeezed by a group that was chatting in front of me. Just as I scooched behind them, the woman closest to me sent an expressive elbow flying backward, knocking my non-alcoholic champagne glass out of my hand and sending a fizz of liquid down my red leather trenchcoat.

“I’m so sorry!” The woman said. She grabbed a handful of cocktail napkins, apologizing, and began to help me mop up. (Another great reason for a red leather trenchcoat: In addition to being a conversation starter, it’s essentially waterproof.)

“Wait—you’re Lane?” she said, finally seeing my now-soggy nametag. She paused her mopping and stood up. “I’m Bronwyn.”

If this was March, I would have assumed this was my prophetically foretold meet-cute.

“I love your all-red look,” she said.

I stand by this.