So maybe “high maintenance” did never leave. But apparently it really started with When Harry Met Sally?

This is a good piece. It’s a “looking back on previous decades’ pop culture, it wasn’t that ‘19 feminist!” piece but with actual insight to it.

Something that needs pointing out, if your two examples of an assertively classifying, questioning man in late ‘80s pop culture are Seinfeld and the Nora Ephron/Billy Crystal/Rob Reiner-crafted character of Harry Burns, is that this is a specifically New York Jewish boomer type

Born maybe still early enough to get a splash of working class Noo Yawk, sandlot baseball and all, but mostly heir to a psychoanalytic culture that valued mastery through self-knowledge, self-knowledge through probing questions

And I’m realizing, by the late ‘80s that was kind of what was left of White urban culture. Well, South Boston. Like you watch the ‘66 Adam West Batman and its picture of Gotham as continuous with small town whitebread culture, just bigger, it would have been mindboggling from the perspective of 1989. Gotham City in ‘89 was a Tim Burton nightmare realm.

Probably more and more true every day now, though, as the rich whites move back to the cities. But I’m realizing how much that’s the point, this stuff was a vision of urbanity for an increasingly tired-of-suburbia White America. “Look, life in cities isn’t tenements and mugging, it’s urbane wit”, Harry and Seinfeld said.

And they invited people back into the cities, and modeled how they should act - as post-religious, post-Freudian, postmodern post-any grand narrative college-educated Jews. Like, Friends, the huge ‘90s back-to-the-city sitcom, one of the things is the guy who gets through life on a cloud of cynical, self-deprecating “Jewish” humor is Chandler Bing, the gentile office guy, to the point that Phoebe had just been assuming he was the whole time.

Kinda was the world I expected to inherit tbh