What Boomer Men Told Me About the Sexual Revolution

It didn’t happen at Woodstock. It happened at a singles bar in the Midwest.

The best man I ever spent time with was born before The Beatles landed at JFK.

This isn’t dating advice and it’s not a nostalgia piece, either, although I understand if it reads that way. It’s something I noticed after more than a decade of spending time with men of every age and emotional condition.

A pattern.

The men who came of age when the rules changed overnight, when the pill was new, when divorce was going mainstream, when meeting someone meant walking into a room and finding out in real time what you were made of, move through the world differently than the men who grew up with unlimited options. They carry themselves like the moment matters.

This is about one of them.

The Kind of Man Who Probably Drives a Buick

He’s late sixties, blue collar Midwest. You can tell he’s got some rough edges, but they’ve been sanded down and polished by now. Twice divorced, not from carelessness. He paid more than he owed both times and didn’t become bitter about it. That alone tells you something most people miss. Divorce doesn’t reveal character. How you behave after it does.

He found me online. Probably on a Dell desktop with a CRT monitor. What I remember is that he introduced himself before he said what he wanted. That sounds like a small thing. It isn’t.

He enjoyed coming to Vegas once or twice a year. Maybe with golf buddies, maybe family, this time he was coming alone.

His watch isn’t expensive, but he’s had it thirty years. His clothes aren’t fashionable, but they fit and they’re clean and he picked them on purpose. He’s the kind of man who seems like he’d drive a Buick or something. Not because he can’t afford better. Because it never occurred to him that the car was the point.

He doesn’t text seventeen times before showing up. He shows up having already decided that this is what he’s doing tonight. No ambivalence. No half-commitments. He made a decision, same way he makes all his decisions. Quietly and all the way.

He’s not emotionally unavailable.

He’s emotionally unannounced.

What he’s feeling shows up in how he moves, what he orders, and how holds eye contact. You find out what he’s carrying by being in the room with him. Not from a disclosure statement.

Photo by Jeffery Erhunse on Unsplash

Plain White Envelope

He arrives with a plain white envelope. Cash, counted beforehand. The kind of envelope you’d pull from a junk drawer next to your stamps and a random screwdriver. He hands it to me and gives me a quick hug. Doesn’t make me ask. Doesn’t mention it.

Handled. Moving on.

I’ve been doing this long enough to know that how a man deals with the money tells you almost everything about how the rest of the evening is going to go. Some men negotiate in the DMs for days. Some split it across two apps so it doesn’t look like what it is. Some try to fold it into “the experience” and hope you won’t notice that the experience doesn’t include paying bills. All that dancing around the money is just dancing around what this actually is.

He doesn’t dance.

He decided what this was before he got here, made peace with it, and brought an envelope.

Envelope’s in my purse. Now let’s have a nice evening.

How He Is in the Room

He listens like someone who learned conversation before there was anything else to do. He doesn’t jump in early, hes able to just let silence stretch until it’s comfortable, not awkward. Most men rush to fill a pause because a pause feels like failure.

He‘s able to let it breathe.

He grew up in rooms where silence wasn’t a void.

Nobody was going to swipe left because of a pause.

He’s funny, but dry. Almost accidental. Like the joke is for himself and you just happen to be lucky enough to be there for it. He asks how I’m doing and means it but doesn’t need a long answer.

He doesn’t dig or perform curiosity. Just checks because that’s what you do when you’re sitting across from another person and you give a damn.

In bed, he’s attentive without being clinical. He reads the room the way he reads everything else, quietly and in real time. He’s not performing. He’s not running a checklist he picked up from the Internet. He’s just present, which after a decade in this line of work I can tell you is rarer than almost anything else a man can offer.

Afterward, he doesn’t reach for his phone. Doesn’t check the time. Doesn’t become a stranger. The transition from intimate to dressed isn’t a gear shift. It’s a slow fade. Like the evening is one continuous thing, not a series of transactions with a awkward seams between them.

Photo by Matthew LeJune on Unsplash

The Sexual Revolution, Where He Learned This

He came of age when the rules changed overnight. After The Pill and before AIDS. No-fault divorce had just become law. The singles bar was a merit based institution, you showed up, you talked to someone, and you found out in real time if there was something there.

No profile. No algorithm. No swiping left or right.

Just you with whatever you had to offer in a room full of humans.

When there are three bars in your county and you might talk to one woman all night, you learn to be in the conversation. Not because you’re a romantic. Because there’s no backup plan in your pocket. There’s no “maybe someone better” a thumb-swipe away. You’re here, she’s here, and this is what’s happening tonight.

Scarcity doesn’t make people noble. It makes them present.

When every moment might be the moment, you pay attention differently.

When every moment is one of thousands, you stop paying attention at all.

He never had thousands. He never had Tinder circa 2012. So he learned to show up properly.

The Chair

Before we leave the room at The Venetian, he pushes the chair back under the desk. Folds the luggage rack flat against the wall. Straightens the bedspread and piles all the towels on a corner. Not performatively, and not for me. I’m leaving too. Not really for the maid staff either. He just does it because that’s what you do when you leave a room. He’s done it a thousand times in a thousand rooms and he’ll do it a thousand more.

He operates on assumptions that don’t require an audience. He just does what he thinks is right without a witness. That’s not a generation thing, exactly. But it’s a thing I almost never see in men under fifty.

On the way out he mentions he’s not ready for this to be over. We’ve known each other several years by now. He asks if I’d like to come back to the Midwest with him for a few days.

Just like that. No buildup. No negotiation. Just something he wants so he asks, and of course I’m game.

So we walk down to The Venetian “Business Center”, he sits down at a Dell desktop, and books two first class tickets home. I sit next to him in another desk chair slowly swiveling myself back and forth with my foot and a wry smile on my face. I can’t help but wonder how many times that well-used Dell in The Venetian Business Center has been used for this kind of “business”. Thousands I’m sure.

The Snow Shovel

O’Hare. Long term parking. January.

We walk to his car and it’s a Buick!

I knew it!

Men who make a big pile of money in a windfall drive Teslas, BMWs, or Range Rovers. Men who make a big pile of money slowly through a lifetime of good decisions drive Buicks. Always a Buick. It’s definitely a thing.

Paid off, clean, nothing wrong with it. And the funniest part, in the backseat there’s a snow shovel. Not a fancy collapsible emergency one from REI. A regular snow shovel. The kind you bought at a big box hardware store in 2008 and grab from the garage on your way out the door because there might be a blizzard while you’re gone and you will be darned if you are going to be stuck at the O’hare airport long term parking lot when you just want to get home.

Clearly, and I say this with all sincerity, I am in the hands of a competent man.

And that’s not a common thing anymore. What would many Millennial men do in that situation? They’d be scampering off to the attendant’s kiosk and ask if a snow plow was going to be coming by.

He planned for the blizzard. He didn’t plan for me. I was the spontaneous part. The shovel was the practical part. Both live in the same man with zero contradiction.

First class tickets bought on a Dell in the business center because he wants a mouse and a 16 inch screen, not a smart phone. A Buick in long term parking. A snow shovel in the backseat. A plain white envelope counted out before he left the house. He doesn’t think in terms of what things signal. He thinks in terms of what things do. And everything in this man’s life is there because it serves a function.

Including me.

That’s not cold. That’s the warmest thing about him. I’m not a status symbol. I’m not a crisis. I’m something chosen with intention, and he made room for it the same way he makes room for everything else. Quietly. Practically. Without apology.

Envelope on the Counter, Twice a Year

He operates on assumptions his generation absorbed. That relationships are durable. That moments don’t need to be documented to be real. That pleasure doesn’t require a TED Talk style public debriefing later. You don’t have to process everything. Some things just are what they are, and the people who know that tend to be better at all of them.

Twice a year. Envelope on the counter. A nice evening or two. It’s never once been complicated. Not because we avoid hard things, but because he decided a long time ago that this was something worth doing, and he does it the way he does everything. All the way, without fanfare, and without asking anyone’s permission.

Photo by Zeke Tucker on Unsplash

Author’s Note:

If you enjoy my non-fiction writing, you may also enjoy my fiction. The first collection is called Je Ne Sais Quoi — three short stories about outsiders and the places that claim them.

Read the first one here. Want all three? They are available on Buy Me a Coffee!