For two years, I played a game to practice the art and science of human connection in every Lyft or Uber ride I took — 350+ rides in total.

Every ride, I'd hop into the front seat and make it my goal to get into as deep of a life conversation with the driver as possible. It didn't matter how much time I had — 10 minutes or an hour. The objective was the same: identify how I could intentionally create deep connection with the human I would be sharing the next slice of life with.

At the time, I was contemplating leaving a marriage to my college sweetheart, a woman I'd been together with for nearly 17 years.

A part of me knew I needed to leave to experience the joy and freedom available in life. And yet another part of me felt afraid of being alone, of starting from scratch to create the level of closeness that it'd taken me 17 years of shared history to build. I didn't have many more 17-year chunks to devote to life partnership.

Little did I know, what I learned about human connection during those rides would change my life and empower my decision to leave.

What Is It Exactly That Creates the Feeling of Closeness?

The idea for the experiment first came to me after listening to Tim Ferris's podcast interview of Brandon Stanton, the creator of Humans of New York.

Stanton approaches total strangers on the streets of New York City, asks to photograph them, and invites them to share their stories — which he then publishes online.

People share all sorts of intimate personal stories — glimpses into their daily lives, their dreams, their fears, and even stories of depression, abuse, sexual assault, and more.

What allows someone to create deep safety and intimacy in such a short amount of time?, I wondered.

I used to be a very reserved and introverted guy — the stereotypical Silicon Valley engineer who felt awkward meeting new people at social gatherings and who felt bored by the small talk.

I viewed myself as uninteresting and had trouble talking about myself.

But I also knew that the feeling of intimacy and closeness was something that I craved in my life.

I struggled with asking my existing friends to hang out with on weekends or to travel with — because I was afraid I wasn’t important enough for them to carve out the time.

I didn't know how to make new friends — not just acquaintances, but close friends — to share the ups and downs of life with.

And so I committed to both reverse engineering the science of deep human connection and developing my own confidence in practicing the art of it.

Those hundreds of Lyft and Uber rides showed me just how intimately two people could share about themselves and feel seen and understood in a short window of time.

I've had complete strangers share their sexual adventures and fantasies. One driver shared how exhausted he felt from his wife wanting sex all the time — they'd committed to having sex at least once every day for a year. Another shared how two passengers had invited him to their hotel room for a threesome — he now packs a spare change of clothes in his trunk just in case.

I've watched grown men cry — from pride for their sons, from how hard they were working for their families, from feeling seen by a total stranger.

I had a driver share his childhood love of singing and dancing and then serenade me and kiss me on the cheeks after a 24-minute ride.

I had a man share how his dad was killed in a gang gunfight when he was 7. To my surprise, he said growing up with a gangster as a father actually made him feel safer. No one wanted to mess with him.

The drivers weren't the only ones sharing.

As I shared parts of myself and my thoughts about a potential divorce, I received so many supportive reflections. One person reflected how I was a butterfly in a cocoon, wanting to be free — the comment hit me to the point of tears. Another even gave me his phone number if I wanted more support.

Lessons from A Training Ground for Human Connection

Looking back, the Lyft and Uber rides were the perfect training ground for learning how to create depth in relationships.

Every ride was a time-bound container. No matter where the conversation went, we knew it'd be over at some point. That made people more willing to engage.

Since we'd likely never see each other again, the transient nature added to a sense of safety for us both to lean into vulnerability.

Because the driver and I were each other's captive audiences, connecting on a human level was easily the most interesting thing we could be doing.

Every new ride also reset me with a clean slate — almost like a mini-Groundhog Day — clearing the impact of any previously failed or awkward experiments.

And because I was taking rides most days, I had ample and frequent practice to try new approaches and observe what worked.

Over time, I learned many things.

I learned to ask curious, open-ended questions. What's your dream? What's important to you about that? What would have to be true for you to make that life change? Yes/no questions ("Do you think...?" or "Is it important that...") can prompt one-word answers that close off more conversations, but open-ended ones invite people to talk about the things that touch their hearts — their families, their aspirations, their values.

I learned to ask vulnerable questions. We often talk about sharing vulnerably — rarely about asking vulnerably. But whenever someone mentions something important in conversation — a divorce, a big life transition, an accident, a death — and then hesitates, that’s a bid for deeper connection. Taking a breath, and finding the courage to invite them to continue takes the conversation to a deeper level. Vulnerable questions — What happened? What was it like? What impact did it have on you? — do exactly that.

I learned to be present during long silences. It can be easy, when we feel uncomfortable with silence, to fill the space with small talk. When we do that, we subconsciously send the message that we're not available for more depth. Sometimes, it's the long silence — particularly after a vulnerable question — that creates the space for the other person to open their hearts.

I learned that when people share something, they’re really wanting connection. They want to know that you’re listening. And when you share how their words impact you, you’re sharing a part of yourself in return. Responding with "Hearing that, I feel..." is one way to connect with them.

Creating Deeper Connection in My Life

The things I learned extended beyond my car rides with strangers.

I started taking what I learned and applying them to other relationships in my life — with my partner, my family, my friends, my co-workers, fellow travelers, new acquaintances.

And all those conversations taught me a radical truth:
Deep intimacy can be created in moments — it doesn't require years.

The closeness I wanted in relationships no longer became a function of time. I didn't need years to create the deep relationships I wanted. Closeness became a function of my intention to create connection and tools like open-ended vulnerable questions in a conversation.

When I realized that, everything changed.

I'd spent large parts of my early adult life overinvesting in my career and underinvesting in my relationships — suddenly I didn't need to feel "behind" anymore.

I started making new, close friends as I traveled around the world — many of whom invited me to their homes for meals or for places to stay.

I didn't have to be afraid of leaving my marriage and feeling alone anymore. Every moment with someone could potentially be a moment of deep intimacy, and I had abundant moments in my life to attract the deeply connected partnership that my heart wanted.

In fact, after leaving my marriage, my first date with the woman who'd become the love of my life lasted six hours in my San Francisco kitchen apartment. In that time, we shared our nervousness. We shared our life dreams. We shared our fears. We cleared up stories we made up about each other that held us back from deeper connection. By the end, with my heart racing, I said, "I'm afraid I'm going to fall hard for you."

I wouldn't have been able to create that level of depth so quickly had it not been for everything I'd learned about human connection up to that point.

We all have relationships that don’t feel as close as we might want them to be. Perhaps there are topics that don’t feel safe to talk about or support that we don’t feel comfortable asking for.

It can be easy to settle for average relationships — either hoping that the relationship will get closer with time or giving up on the level of closeness we want entirely.

You deserve more. We all do.

There's another option: We can consciously create more intimacy-defining moments in our relationships and have the depth of connection that we truly want.

The amazing thing about connection is that it is a 100% learnable skill.

However, with the rare exception of Stanford's well-known "Touchy Feely class", the skill is almost never taught in school.

That's why my partner and I will are building a company to teach it. We’ll be distilling everything we know into experiences that leave you feeling confident and equipped to create the connection you want in your life — whether it's with your partner, your friends, your family, your co-workers, your date, or someone else important to you.

Thanks to Ryder Jackson, Wes Lambert, Russell Sprole, Lyssa Menard, Nic Hurrell, and Candace Sauve for reading early drafts of this post. ❤️