In my last newsletter, I dissected the messy dynamics of the PolyFamily show—a cautionary tale of non-monogamy gone wrong.
This week, I’m starting something new: Reports from the Streets—a little series that will pop up from time to time, sharing stories of organic romantic connections (or attempts at them) that have happened to me in the wild. The ones that stand out as thoughtful, attuned, or just refreshingly human.
This first story was inspired by my friend Allie Hoffman, who recently wrote a sharp critique of how AI and dating apps are warping the way we meet and connect. She’s long been a skeptic of algorithm-driven romance—and in her latest post, she writes:
“We’re outsourcing one of our most personal and intuitive experiences—attraction—to predictive models designed to optimize engagement, not connection.”
👉 You can read her full piece here.
I couldn’t agree more. While dating apps can absolutely play an important role—especially for people in rural areas, or with niche preferences or needs—they’ve also created a kind of dependency. For many of us, especially those living in cities surrounded by potential connection, they’ve replaced something we haven’t actually lost: the possibility of magic, in real time.

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And while I’ve used dating apps at different points in my life, I’ve always believed that some of the most meaningful moments of connection happen off the apps—in unexpected places, when we’re open to the spark of chemistry and bold enough to act on it.
So today, I’m kicking off this new series with one such moment—a real-life example of how a respectful street approach can still feel sweet, safe, and surprisingly lovely.
The Frankie Encounter
I was walking through Prospect Park, where I live now, when I noticed a runner cutting across the path in front of me—finishing his workout with a kind of triumphant, arms-outstretched victory pose.
I couldn’t see his face at first, only his back. He was shirtless. Ripped. Glowing with post-run sweat. A small reward for being in the right place at the right time.
A few moments later, he sat down on a bench just as I was passing by. We locked eyes. I gave him a small smile and nod—a brief gesture of acknowledgment and appreciation. Nothing more. And I kept walking.
But a minute later, he caught up to me.
He jogged ahead, turned around, and offered a high-five—then told me he doesn’t usually do this sort of thing, but that the look I gave him gave him the courage to say hi. He admitted he was more of a monogamous guy, but seemed genuinely curious. Nervous, but not in a performative way—in that real, “I know this is risky” kind of way.
He asked for my name. When I told him, his jaw dropped—like actually dropped. Turns out his ex-girlfriend was also named Zhana. She used to live on the other side of the same park. “She really left a mark,” he said. “I still think about her.”
Turns out, as often happens with my name, it was a different Zhana—Spanish spelling, different origin. But still… a sweet little twist of connection.
Then he asked for my number.
I told him I wasn’t going to give him my number—that I had a partner, an equally ripped and beautiful man I adore, and we’re not currently seeing other men. But I offered to take his email and add him to this newsletter list—just in case things open up again in the future.
He looked a little confused by all the openness talk, but gave me his email anyway. We smiled, said goodbye, and I kept walking.
What He Did Right
Street approaches are risky—for both parties. They can feel intrusive, unsafe, cringey. But when done right, they can also be delightful. Here’s why Frankie’s earned an A:
- He read the signal. He didn’t cold-approach out of nowhere. He picked up on a smile and nod—a subtle but deliberate green light.
- He was confident but not cocky. He made his move with clarity, not arrogance. No weird pickup lines, no performance. Just genuine curiosity.
- He respected the no. When I said I wasn’t available, he didn’t sulk or lash out. He accepted it with grace—a sadly rare but essential skill in flirting.
- He didn’t linger. The exchange was brief, respectful, and energy-matched. He said his piece, listened, and exited.
- He made it feel safe. There was no looming, cornering, or tone-policing. I never felt trapped. That’s huge.
So Frankie—if you’re reading this—thanks for the A+ street approach. You made my day, and gave me hope for a world where people can still connect… without an algorithm.
Why This Matters
There’s nothing groundbreaking about this story—and that’s kind of the point.
It was just a moment. A flicker of connection. A respectful risk, taken by someone who read the signals, made a move, and accepted a no with grace. No pressure. No entitlement. Just a glimmer of human curiosity between two strangers on a sunny day.
This shouldn’t be rare. But for a lot of people—especially men—it is.
Because approaching someone in public carries real risks. The risk of rejection, obviously. But also the risk of coming off as creepy, pushy, or unsafe. And for women, those risks are reversed: the fear that a no might not be taken well. That an innocent exchange might escalate into something threatening.
What made this work—what made it feel good—was the attunement. He read my body language. He responded to an invitation. He made a move, but not a grab. He accepted a no with a smile, not a sulk or a slur.
We need more of this. Not just to reclaim the art of flirtation, but to bring more humanity back into how we meet, connect, and explore the spark of possibility.
Ever had a moment like this? I’d love to hear about it—just hit reply and tell me your story!
We’re living in a time when gender scripts around flirting are confused and shifting. Men are scared to approach. Women are taught not to signal. Algorithms are deciding who we meet—and most of those “connections” go nowhere.
But it doesn’t have to be that way. If you’re a woman and you see someone you’d like to be approached by—signal it. Smile. Make eye contact. Say hi.
And if you’re a man, and you feel the nudge—read the room, take the risk, and be respectful.
Flirting is a dance. It can still be fun, spontaneous, and human. Let’s not lose that.
With love,
Dr. Zhana