‘Gilmore Girls’: Alexis Bledel on the Storyline That Didn’t Make ‘a Lot of Sense for’ Rory Gilmore

Rory Gilmore’s love life is a hot topic among fans of Gilmore Girls even years after the TV show’s gone off the air. Alexis Bledel, the actor who played Rory, has her own feelings on her TV counterpart’s romances. Namely, everything that happened between Rory and Dean Forester (Jared Padalecki).

On ‘Gilmore Girls’, Rory Gilmore dated Dean Forrester for 2 years 

Alexis Bledel and Lauren Graham as Rory and Lorelai Gilmore on 'Gilmore Girls'
Alexis Bledel and Lauren Graham as Rory and Lorelai Gilmore on Gilmore Girls | Warner Bros./Delivered by Online USA

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When Gilmore Girls debuted on Oct. 5, 2000, viewers met Rory as an ambitious straight-A student at Stars Hollow High. About to transfer to Chilton, a prestigious private school that would hopefully get her one step closer to Harvard, Rory meets Dean. 

A new student who just moved from Chicago to the fictional town of Stars Hollow, Connecticut, Dean likes Rory. They have a slightly awkward conversation on the way to Miss Patty’s (Liz Torres) and Rory has change of heart about wanting to go to Chilton. 

Ultimately, she decides to switch schools, and, over the course of the show, Dean becomes Rory’s first boyfriend. Much to Lorelai Gilmore’s (Lauren Graham) relief, Dean is everything she’d want in a first boyfriend for Rory.

Dean Forrester and Rory Gilmore broke up over Jess Mariano on ‘Gilmore Girls’

Apart from an ill-fated school dance and a brief split, it was smooth sailing for the couple.

But it all changed when Jess Mariano (Milo Ventimiglia) came to town. Luke Danes’ (Scott Patterson) nephew, Jess is a bad boy who gets along with no one in town except Rory. 

Jared Padalecki, Alexis Bledel, and Milo Ventimiglia at the 2003 Teen Choice Awards presenting an award
Jared Padalecki, Alexis Bledel, and Milo Ventimiglia at the 2003 Teen Choice Awards | Ray Mickshaw/WireImage

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A love triangle between Rory, Dean, and Jess ensues. Things take a turn at the town’s dance marathon in Gilmore Girls Season 2 Episode 7: “They Shoot Gilmores, Don’t They?”

Dean breaks up with Rory because she so obviously likes Jess and has for a while. Rory and Jess go on to date until Rory heads off to college. Although Dean’s not out of Rory’s life completely, they remain friends. 

Alexis Bledel ‘surprised’ by Rory Gilmore and Dean Forrester’s hook up on ‘Gilmore Girls’

In Gilmore Girls Season 4 Episode 22: “Raincoats and Recipes,” Rory and Dean have sex. Rory’s first time, the moment causes major conflict between her and Lorelai.

Why?

Because at the time, Dean’s married to Lindsay (Arielle Kebbel) and cheating on her with Rory. 

Alexis Bledel at the 2017 Emmy Awards
Alexis Bledel at the 2017 Emmy Awards | Jason LaVeris/FilmMagic

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In a 2016 interview with Entertainment Weekly, reflecting on Rory and Dean’s first time having sex, Bledel said the circumstances surrounding it took some getting used to.

“Over the years, I was definitely surprised by certain plot twists,” Bledel said. “That was one of the things that surprised me. I didn’t think that it was something that made a lot of sense for my character,” she said referring to Dean and Rory’s hook up.

“[Amy Sherman-Palladino] likes a little bit of a shock value, so it was something that I had to wrap my head around,” Bledel added.

Taking place at the end of season 4, Rory and Dean proceed to have an affair in the following season of Gilmore Girls. It causes strain on Rory’s relationship with Lorelai before the two call it quits for good.

Watch every season of Gilmore Girls and the revival on Netflix.

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