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The entirety of Freddie DeBoer's life outlook is that he loved hippies/bohemians in new york in the 90s and then turned out to be quite smart and a world view crystalized around that abstract attraction/memeplex. It was pretty clear in his infamous planet of cops piece and it explains exactly why he lives in a groundhog world of noticing the left has lost it's mind but waking up the next day completely forgetting that realization.

As for the 90s vs today, the tech sucked and was expensive, the domination of the moral majority sucked even though it's piercing light gave contrast to interesting subcultures just as much as modern progressivism sucks despite it's life giving contrast to communities like our own. The grass is greened by the lack of our, or at least my, current enemy but there is a cause for the sword in every era.

I think this is it. I wondered about his hatred of Friends and then it struck me: he was that sorta middle-class not really fashionable white guy. He dislikes Friends because he wanted the romantic, hipster, cool, back in The Village when The Village was The Village vibe, and Friends was just too ordinary for him. That coffeeshop with the pun name where he got his overpriced cup of java? That was Central Perk, not some boho artsy joint of the 50s/60s, even as he pretended it wasn't.

Friends was the reality of city life for late 20s-early 30s college-educated or at least drop-out white people who moved there, not the romantic notion he desperately wanted to live and convinced himself he was living, because he was (the equivalent of) a starving artist in a garret:

You might picture a bunch of stylish Gen Xers trying to balance the era’s fixation on authenticity with the need to pay the rent. You might imagine them going to underground clubs and hearing music by independent artists on the come up. You might picture them in clothing that reflected the styles of the era, not necessarily flannel and bomber jackets but something that expressed at least a modicum of interest in contemporary fashion. You might think of their coffee shop as being a cool out-of-the-way place where the connoisseurs go, someplace with low lighting and a savvy clientele. You might assume that the New York they move around in is a hip site of artists and thinkers, the outsider’s New York that’s been dramatized in so many television shows and movies.

That's why he did that piece moaning about Friends. It drew back the veil and made him face the fact that he's not the cool kid he always wanted to be.

I do like Freddie, and I think he often writes good sense, but come on dude: Friends was just as aspirational for a lot of people who weren't American (and even a lot who were) who wanted that cool city living life just like you wanted, except you wanted the jazz artsy boho scene of the Beat Generation.

He's talking about the continuing popularity of Friends and if you read the piece, he clearly finds the premise of the show distasteful. If he was 14 when it aired, why the hell does he care that the show didn't have the kind of Cool Gen X Fashion about going to obscure clubs with savvy clientele? He's plainly unhappy with the view that it gives about NY, when he moved there for the romantic dream of city life. He wanted to be the cool city life guy, and now everybody's mental image of that time is Friends.

Right now Freddie is living the Ross or Chandler life, not the cool hipster life. Of course he doesn't like the comparison. Seinfeld also gets more hip cred than Friends , even if it's about a small bunch of sort of weird people hanging out in a friend-group, possibly because of the overlap with Jerry Seinfeld's real (professional) life as a stand-up comedian and the part he played in the show.