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K

Dean is boring on purpose. If he didn’t cheat on his wife, he’d be that quintessential small town safe man who was a good provider that the women who didn’t leave after high school would want to marry. Works hard, would be a good provider, etc. Find someone with shared values and he could live a comfortable, peaceful existence. The problem is that this isn’t the life Rory is suited for. She’s trying to relive the good old days because college is hard. She wants a job where she travels. She likes dinner with the rich grandparents. Can you really imagine Dean having a nice dinner with Emily these days?

em9397

Dean was the new kid from Chicago in S1 who could keep up with Rory and Lorelai's quick wit and references. He appeared relatively intelligent and well-rounded, though a little territorial. When smart and hot-headed Jess arrived from New York ONE year later, the writers removed half of Dean's brain cells and turned him into a small-town kid with no life goals or prospects. It's a shame because Dean was a good first bf for Rory in S1, and I wish he could've at least kept some of the character traits/backstory from his introduction. They didn't have to dumb him down.

DaniJay

That part! I’m not the biggest Dean fan (especially this season), but I’ve always hated what they did to his personality when Jess showed up. That always felt like such lazy writing to me. Like you mentioned, season 1 he’s moves in from one of the biggest cities in the US, and he gets all the movie references and he and Rory constantly exchange books, etc. And then Jess comes in and suddenly Dean was the stupid “small town” hick jock that had no desires after high school?! Season 1 Dean and season 2 Jess have a lot of stuff in common actually lol Jess was just more of the brooding bad boy. They could have really played with that dynamic between them, even like the Chicago/NewYork rivalry lol