Dean Forrester was Rory Gilmore’s very first boyfriend. The tall, “new kid” appeared during the pilot of Gilmore Girls and pretty quickly cemented himself in Rory’s life. For nearly two full seasons, Dean seemed largely perfect. Then, he started to change. By season 3, Dean was whiney, difficult, and frankly, a bit unhinged. When he reappeared in seasons 4 and 5, Dean was nearly unrecognizable, and by the time he walked away for the last time, after a verbal spar with Luke Danes, he was pretty awful. Why did the showrunner, Amy Sherman-Palladino, opt to ruin Dean? Maybe she ruined Dean’s character to make Jess Mariano, Rory’s second love interest, look much better. It sort of worked.
Dean Forrester became much more controlling once Jess Mariano showed up
Dean Forrester was, by all accounts, the perfect first boyfriend. He showered Rory with attention, gifts, and affection. He mostly accepted some of her quirkier personality traits and was committed to not holding her back. Dean even acknowledged that Rory was committed to Chilton, first and foremost, for the first year of their relationship. To be fair, until Jess Mariano showed up in Stars Hollow, Dean was pretty much the perfect catch.
Once Jess arrived and showed interest in Rory, things started to change. Dean became clingy, combative, and downright controlling. Dean also slighted Rory by breaking up with her in front of almost the entire town. All told, his behavior toward the end of their second relationship was nothing short of terrible. Things only got worse with Dean.
Dean’s season 5 ‘Gilmore Girls’ arc ensured he was way worse than Jess ever was
Jess disappeared on Rory at the end of season 3, opting to leave Stars Hollow without letting his then-girlfriend know. That was after he tried to pressure her into having sex at Kyle’s house. Jess also spent months trying to get her interested in him, only to put in minimal effort once he had her. Rory graduated from Chilton and started her freshman year at Yale, all before Jess resurfaced. All told, Jess wasn’t great to Rory before, during, or after their relationship, but somehow he seems to be leaps and bounds better than Dean.
Why is that? Simply put, Dean became perhaps the worst possible person by season 5 of Gilmore Girls, erasing all of his good qualities in the process and making Jess look better. He married Lindsay Lister when he was still in love with Rory, then jumped at the opportunity to have sex with Rory, despite his marital status. Dean then went home to yell at Lindsay for answering his phone and never bothered to come clean. We are confident that Dean would have never mentioned the indiscretion if Lindsay hadn’t found Rory’s letter.
To make things even worse, Dean snapped at Rory as if the entire situation was her fault. He barked at her again when she suggested going out in Stars Hollow together. Still, he was fine with the idea of hooking up. He then proceeded to break up with her, again, in front of a crowd of people.
When you really examine the situation, Jess’ flaws and mistakes pale in comparison to Dean’s late-season behavior. It’s hard to imagine Sherman-Palladino didn’t do it on purpose but has anyone ever verified the theory? No one associated with the show has.
Amy Sherman-Palladino doesn’t like how much fans focus on Jess and Dean
So, did Sherman-Palladino purposefully dismantle the character to make Jess look better? She certainly isn’t giving the information away if she did. In the years since Gilmore Girls wrapped its final season, the showrunner has made it clear that Rory’s boyfriends were never supposed to be such a significant element in her story. Based on several statements, it seems she didn’t give Dean and Jess’ story arcs all that much thought.
She told Time that the boyfriends were only supposed to be a part of Rory’s development. She said, “Dean was her first boyfriend, that Jess was the boy that diverted her attention. Then she wound up with Logan.” According to Sherman-Palladino, the rivalry was never supposed to be all-consuming. Still, the timing of Dean’s downfall seems pretty coincidental. It certainly allowed Jess to look like a better match, despite all his glaring flaws. So, does that mean Logan Huntzberger was ultimately her best boyfriend? It’s impossible to say.