Dean Was Perfect For Rory, Until Gilmore Girls Ruined Him

The Great Rory Boyfriend Debate has been raging on for almost two decades now — bitterly dividing friend groups between those who yearn for the tortured bad boy Jess Mariano and those who can’t help but swoon at Logan Huntzbeger’s charming wit. And then there’s Dean. For all the discourse around which Gilmore Girls boyfriend reigns supreme, Dean Forester is clearly lagging behind Rory’s two other major romances. I can see why, but I also think there was a point when Dean was the perfect match for Rory.

Stop yelling at me! Look, I know Dean is The Worst™ for most of Gilmore Girls: He’s aggro, possessive, and honestly, kinda dumb. But that’s Seasons 2 to 7 Dean, and he’s a completely different person from Season 1 Dean. Before the writers basically gave him a lobotomy and completely flipped his whole character, Dean was the clever, book-loving outcast who could match Rory’s wit and go out of his way to take care of her.

If you’re thinking, “Wow, that sounds like another certain leather-jacket-wearing sadboy from Stars Hollow,” you’re right. Season 1 Dean was basically Jess before Jess came into the picture, except Dean was able to comfortably incorporate himself into Rory’s life rather than trying to drag her away from her mom and friends. This initial version of Dean maintained his alluring mystique while also embracing movie marathons and tables full of takeout with Lorelai, connecting with the Gilmore girls on a core level.

It’s pretty glaring to compare what Dean was like in Season 1 to what he became after Jess arrived in Stars Hollow in Season 2 — it’s as if Dean’s whole essence was transferred to the new guy. Now Jess was the brooding bookworm, and Dean had somehow become a braindead jock who’d stopped caring about connecting with Rory and only saw her as an object to protect. Going absolutely ballistic over a picnic basket? Dean, this isn’t you, baby!

I shouldn’t be too harsh on this sudden change. There may have been a few signs of Dean’s underlying issues even in his Season 1 peak, like when he told Rory that he could see the appeal in a regressive ’50s-style housewife. (He was low-key ahead of the curve on the tradwife trend... not that that’s a good thing.) And his freakout over Rory not saying “I love you” back to him was a mark of his emotional immaturity.

But these slight cracks weren’t enough to warrant a 180-degree character change. It seemed like once Jess came into the picture, the show’s writers did everything they could to vilify Dean in order to push Rory closer to Jess. And hey, it worked! Jess became the ultimate Gilmore Girls crush, and all memory of Season 1 Dean was lost behind his new toxic jock persona and questionable bowl cut.

Maybe the allure of Season 1 Dean could all be chalked up to his mystique, and he really was hiding that possessive monster beneath the bookish sweetheart the whole time. Or maybe — just maybe — Jess is actually an energy vampire who stole Dean’s whole personality when he flew into Stars Hollow. Whatever the case, I’d say Rory actually had a pretty good first boyfriend... until he turned into someone else.