May 17. A warm Saturday night in Wicker Park, a vibrant stretch of Chicago where seven restaurants crowd a single block.
Troy and I were having dinner at Mama Delia, one of the quieter spots. The sidewalk patio held five tables: three two-tops, including ours, and a pair pulled together for a group of eight women. At those tables, Troy was the only man.
The scene was beautiful — low lights, shared plates, shoulders angled in. The kind of evening people wait for all winter. Still, I found myself watching the crowd as it moved past us: women walking in pairs or alone, dressed with care. At table after table at the nearby restaurants, there was a noticeable absence of men — at least of men seated in what looked like dates.
Troy and I have known each other for almost 20 years. We met at Playboy, of all places, back when we were both learning how desire gets packaged, sold and sometimes misunderstood. We stayed close friends, bonded not just by our opinions, but by the effort it takes to stay in someone’s life.
That night, we made the effort. Still, what I saw unfolding around us felt like something else entirely: a collective shift I couldn’t unsee.
It started to become clear the previous April, when a man who had been pursuing me canceled a dinner at the last minute. There was a scheduling mix-up with his son’s game. I understood. I’m a hockey mom; I get it. Still, I went. I wore what I would have worn anyway. I took the table. I ordered well. And I watched the room.
Only two tables nearby seemed to hold actual dates. The rest were groups of women, or women alone, each one occupying her space with quiet confidence. No shrinking. No waiting. No apologizing.
That night marked something. Not a heartbreak, but an unveiling. A sense that what I’d been experiencing wasn’t just personal misalignment. It was something broader. Cultural. A slow vanishing of presence.
I spent over a decade behind the curtain of digital desire. As the custodian of records for Playboy and its affiliated hardcore properties, including sites like Spice TV, I was responsible for some of the most infringed-upon adult content in the world. I worked closely with copyright attorneys and marketing teams to understand exactly what it took to get a man to pay for content he could easily find for free.
We knew what worked. We knew how to frame a face, a gesture, a moment of implication — just enough to ignite fantasy and open a wallet. I came to understand, in exact terms, what cues tempt the average 18-to-36-year-old cis heterosexual man. What drew him in. What kept him coming back. It wasn’t intimacy. It wasn’t mutuality. It was access to simulation — clean, fast and frictionless.
In that world, there’s no need for conversation. No effort. No curiosity. No reciprocity. No one’s feelings to consider, no vulnerability to navigate. Just a closed loop of consumption.
What struck me most wasn’t the extremity of the content; it was the emotional vacancy behind it. The drift. The way many men had quietly withdrawn from intimacy and vulnerability. Not with violence or resistance, but with indifference.
They weren’t sitting across from someone on a Saturday night, trying to connect. They were scrolling. Dabbling. Disappearing behind firewalls, filters and curated personas. And while they disappeared, women continued to gather. To tend. To notice who wasn’t arriving — and to show up anyway.
I’m 54. I’ve been dating since the mid-80s, been married, been a mother, gotten divorced, had many relationships long and short. I remember when part of heterosexual male culture involved showing up with a woman to signal something — status, success, desirability. Women were once signifiers of value, even to other men. It wasn’t always healthy, but it meant that men had to show up and put in some effort.
That dynamic has quietly collapsed. We have moved into an era where many men no longer seek women to impress other men or to connect across difference. They perform elsewhere. Alone. They’ve filtered us out.
I recently experienced a flicker of possibility. With James. We met on Raya, the dating app. There was something mutual from the start — wordplay, emotional precision, a tone that felt attuned. It was brief, but it caught light. I remember saying to him, “Even fleeting connections matter, when they’re mutual and lit from the inside.” I meant it.
There was just enough spark to wonder what might unfold. Enough curiosity to imagine a doorway. But he didn’t step through it. Not with a plan. Not with presence. He hovered — flirting, retreating, offering warmth but no direction.
Sexual tension and a spark aren’t reason enough to sit still and hope there’s substance behind the shimmer. So I named what I felt. I texted him clearly, with care, not simply to declare attraction but to extend a real invitation to explore what was possible. I didn’t chase. I invited, leaving the door open. If he ever wanted to cross the threshold — not just to take, but to meet — I was willing. I wanted. I still do.
He never replied. He still follows my Instagram stories — one of those small gestures of passive engagement that so many of us now mistake for closeness. It looks like interest. It feels like silence.
There are thousands of Jameses. I have known dozens. The arc varies, but the undertow is familiar.
What I won’t entertain is directionless orbiting. That thing so many men now seem to mistake for connection: the perpetual maybe. The emoji check-ins. The casual “seeing where it goes” without ever going anywhere. We call it a situationship. But mostly, it’s avoidance. An abdication of ownership — of feeling, of behavior, of sex that isn’t a means to an end, but is communion.
There was a time, not so long ago, when even a one-night stand might end with tangled limbs and a shared breakfast. When the act of staying the night didn’t announce a relationship, just a willingness to be human for a few more hours. Now, even that kind of unscripted contact feels rare. We’ve built so many boundaries that we’ve walled off the very moments that make connection memorable. And frankly, morning sex is often the best sex. Sometimes you even get a side of eggs before you disappear from their bed and their life forever.
This idea that vulnerability is a threat instead of an invitation has created a culture of hesitation, of men circling intimacy but never entering it. And the result is thousands of tiny silos. Everyone performing closeness, but no one making a move that binds. Isolation. Loneliness. A hunger for contact that has nowhere to land.
Maybe we’re between paradigms, mourning what’s fallen, not yet fluent in what comes next. The infrastructures of intimacy — slowness, curiosity, accountability — have been eroded by haste, convenience and a kind of sanctioned emotional retreat.
It’s not about blaming men. It’s about noticing the imbalance. About grieving what’s not meeting us. And about refusing to dress it up as personal failure when it’s actually a collective reality.
So here’s what I’ll say: You are missed. Not just by me, but by the world you once helped shape.
We remember you. The version of you that lingered at the table. That laughed from the chest. That asked questions and waited for the answers. That touched without taking. That listened — really listened — when a woman spoke.
You are not gone, but your presence is thinning. In restaurants, in friendships, in the slow rituals of romantic emergence.
You’ve retreated — not into malice, but into something softer and harder all at once: Avoidance. Exhaustion. Disrepair.
Maybe no one taught you how to stay. Maybe you tried once, and it hurt. Maybe the world told you your role was to provide, to perform, to protect — and never to feel.
But here’s what’s real: We never needed you to be perfect. We needed you to be with us. Not above. Not muted. Not masked. Just with.
And you can still come back. Not by becoming someone else, but by remembering what connection feels like when it’s honest and slow. When it’s earned and messy and sacred.
We’re still here, those of us who are willing to cocreate something true. We are not impossible to please. We’re not asking for performances.
We are asking for presence. For courage. For breath and eye contact and the ability to say, “I’m here. I don’t know how to do this perfectly, but I want to try.”
Come back. Not with flowers or fireworks, but with willingness. With your whole, beautiful, imperfect heart.
We’re still here. And we haven’t stopped hoping.
As for me, I’ll keep showing up. Not because I’m waiting. Because I know what it feels like when someone finally arrives.
Rachel Drucker is an intellectual property professional in Chicago.
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