Where to Find the Most Interesting Conversations (And Their Lasting Importance)
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As I drove my first twin to college, we had one of those in-between conversations. A pause from how to create a first impression with professors, roommate conflict resolution, and strategies to circumvent the freshman 15.
She told me: I pay attention to the oddballs. The ones who say bizarre stuff that makes no sense at first. The ones who don’t think like you with near-zero interest in blending into a self-limiting group. My face hurt from smiling. I love it when the roles reverse: the young get it more than adults who start to clamp down on the small range of people who win face time with increasingly rapid rates of tossing new characters to the curb.
As much as I love sitting with people who have PhDs in psychology, philosophy, economics, or the minds who write books that reshape worldviews, few of them compare to the spark from someone off the grid.
Weirdness interrupts your autopilot. It forces you to see the world tilted at 37 degrees and suddenly you notice things you missed. Even if they’re wrong. Let me repeat: even if the weird guy or gal is wrong.
The Conversation That Stuck
When I transferred to Cornell University, I didn’t know where I fit. I missed the freshman year of immediate bonding from leaving home for faux independence. Most days I drifted with a bunch of pale frat boys, and he was always with his crew, Black men, tight as a unit. We never crossed, despite the occasional gym spotting.
Then came a snowy night (straight out of a John Irving novel - click). Flakes big enough to show their shapes, sticking to my coat, my arms. The campus was quiet, emptied out. He was the only person in sight, sitting on a bench under a streetlamp, reading. He looked like a man who wanted to be left alone. But the light over him made it impossible to focus on anything else in this panoramic image.
He held The Celestine Prophecy. I had been forcing myself through The Fountainhead. Neither of us had heard of the other’s book. That was the start. He didn’t stay seated. He stood, animated, telling me why his book mattered, just alive with it. I asked questions, he fired back. Before long we were both on top of the bench’s backrest, talking fast.
We never became close. But whenever we saw each other after that night, he’d call out “Yo Kash,” pull me into a hug, then go back to his crew. No small talk or pretense. This thing between us didn’t need maintenance.
At graduation, robes on, caps tilted, we spotted each other. Stopped three yards apart. “Remember our conversation?” he asked. “That’s what college is about.” We hugged, thick and solid as his friends looked at me askew as if to say who the fuck is this white boy, and then walked off.
That’s why you seek out weirdness. People who crack the pattern. The ones who throw you into a conversation that breaks the script. An infinitesimally small act of epigenetics, where you are somehow changed.
That moment still sits with me. A single night, one strange overlap, two books we didn’t know, and a conversation that outshone most major college events.
As I tell my kids, choose the interesting path because it has the potential for the greatest impact. It’s one of those naturalistic well-being interventions:
The Behavioral Evidence
This video captures it better than I can. Watch it, and then ask yourself: Who’s the weirdest person in your circle? And why aren’t you talking to them more?