82. 200 dating profiles: horizontal with a superconnector (1 of 2)
Play • 1 hr 2 min

Welcome to horizontal, the podcast about intimacy of all kinds, recorded while lying down, wearing robes. I know I said that Season 3 would be threesomes all season long, but we will still have the occasional dyad, because, sometimes it just works out best that way.

In this episode, I lie down with Steve Dean. Steve Dean is a dating expert, a MmmmEGAConnector, an adventurer, a perpetual nomad, and an event SuperHost. He’s the founder of the dating industry consulting firm dateworking (which you can find on dateworking.com). He stewards workshops, dinners, coworking sessions, and massive meetups like the food-court-centered Hygge [HOO-GAH] (which means cozy in Danish).

Steve Dean intentionally dates people from all different parts of the social spectrum, including those he would never introduce to his friends, in order to understand their perspective on the world. I think he’s actually an anthropologist at heart, and dating is the Tribe he studies. He’s a quintessential participant-observer. His experiences are research. His research is experiential. His brain incessantly crunches data, and relentlessly seeks for the most optimal of the optimal outcomes. I’ve never met a human machine quite like him.

One week this February, I had the mean blues, and I reached out to my friend Jillian, patron of the podcast, and creator of The Joy List, a weekly compilation of events that one can go to alone, and leave with a new friend. I asked her what she was excited about that week and she rattled off three or so happenings. Then she asked, “How about you?” And I realized that I wasn’t excited about anything that week. I had, in essence, nothing to look forward to. So Jillian decided to fix that. She encouraged me to go to Open Brain, a roving salon for art and ideas that takes place in living rooms and public parks and spaces in-between. This was a living room edition. I almost didn’t go, I was just feeling so blah. But I eventually dusted off a tango song I used to sing, and showed up.

At Open Brain, two things happened in quick succession: I met a man from San Francisco, Michael, who became my lover, and he invited me along to an after-event hang in a hotel lobby in the Financial District. There I would meet Steve Dean, who was orchestrating the event. Everyone kept saying his name. Nobody said his first name on its own. He was Steve Dean to everyone. Jilian said, “You don’t know Steve Dean? Oh. You should know Steve Dean.” That clinched it. And so I went along to talk Burning Man with Michael, and meet Steve Dean. When Steve Dean and I met, I told him, “Jillian said that we should know each other.” Steve said, “What’s your name?” “Lila,” I said. “What’s your last name?” A bit bemused, I said, “Donnolo.” “Yep,” said Steve Dean. “We should know each other.” And then we talked intimacy, dating, and why teenagers are having less sex these days, until the wee hours.

Because I had recently curated my intimate immersive Valentine’s experience at Hacienda Villa, 14 Rooms, Steve consulted me about his love-language-themed townhouse full of intimate encounters, The Love Immersive, set for March 30th, and invited me to be a part of it. Knowing that the environment would be overwhelming — potentially magnificent, but certainly overwhelming, I set up a breather-space. A closet with a cozy mat, blanket, and pillow set-up, like a child’s secret hiding spot, with three headsets programmed with an 11-minute audio experience I pre-recorded, about the upper limits problem, catching it in time, and the radical recalibration of rest.

The day of the Love Immersive, Michael was back in town from SF. I hadn’t seen him in three weeks, and we had ferocious, pounding sex that soaked all the way through my mattress cover. That night, at the Love Immersive, juiced up and well-fucked and sex-haired and satisfied. I met my current partner, Patrick.

Because Steve Dean is a Superconnector, I’m in the most communicative, loving romantic relationship of my life so far.

In this, the first half of our conversation, we talk about VR World, where Steve met Patrick, my tendency to codependency, Steve’s dating habits, whether connection or commitment requires compatibility, optimization the skill of connection, dating across 200 different dating apps, the Sex on Demand app, whether comets are partners, or if they might be growth charts, polyamory as part orientation and part skill-set, how relationships are like start-ups, and the libido-killing cycle that Patrick and I found ourselves in at the outset of our relationship.

In other words, come lie down with us in Chelsea, on the island of Manhattan, New York.


P.S. Cats were drugged in the making of this episode. And by cats I mean: one singular cat. And by drugged I mean: with catnip. Still. I thought it was important to tell you.

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