Not surprisingly, the heartthrob that was Troy is now on many “most hated characters” lists (including Patton Oswald’s), but back then — to a teenage girl — he was dreamy and unwilling to compromise his artistic soul for… ugh, make it stop. Lelaina, on the other hand, is still a pretty great character, and stylish one at that. And part of it is due to Winona Ryder’s ability to capture that realm between awkwardness and stylishness (Kristen Stewart also has this ability), making everything look almost, but not quite, effortless — a good place to be.  

As a recent college graduate with a degree in film and no job prospects (I’ve been there!), Leilana’s clothing fits nicely in that commercialized grunge moment when grunge was no longer a real thing. In other words: Marc Jacobs, without actually using his clothes. So, oversized t-shirts and faded ’90s jeans (best jeans ever, before they got too skinny — usually Levi’s 501s.), a shirt dress that says “I’m smart,” some kind asexual grandma floral frock, a pair of Chucks, and a clog-type of a shoe or — even better — a Mary Jane clog for special occasions. She has cool, sweet, unkempt hair and wears no makeup. She smokes a lot and says things like “the most profound, important invention of my life: the Big Gulp.” 

All of it sounds dreadfully boring but so charmingly ’90s. It’d be rare to see a mainstream twenty-somethings romantic comedy these days without the characters being decked out in designer duds and having some cool job (like, the male lead would be an architect and the female protagonist would work in publishing, or something like that). So when dreamy, greasy-haired slacker Troy says “You see, Lainie, this is all we need: a couple of smokes, a cup of coffee… and a little bit of conversation,” you buy it. It was good enough for ’90s. I wonder what Lelaina and Troy are doing now? (I bet you he’s 40 and insufferable, and she works for CW.)

Memories? Ok, go.