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…