There’s an ever so slight chill in the air, and that means one thing: Fall. Leaves change color, pumpkin spice takes over for all other flavors, and everybody rewatches Gilmore Girls. It’s Stars Hollow season whether you like it or not, so it’s time for the annual revisiting of all the men Rory Gilmore dated and then cast aside, starting with Dean Forester.
Now let’s be real. When it comes to Rory Gilmore’s boyfriends, Dean never should have stuck around beyond high school. Jared Padalecki played Gilmore Girls’ quintessential high school boyfriend, the cute, mysterious new boy at Stars Hollow High who made Rory (Alexis Bledel) almost give up a spot at the exclusive private school Chilton. His height and floppy hair made up for the fact that he wasn’t the sharpest tool in the shed, but he was a great first boyfriend for Rory Gilmore.
Unfortunately, he wasn’t just her first boyfriend. After she left him for Jess Mariano (Milo Ventimiglia) and Dean moved on with a woman named Lindsay, who he eventually married, Rory returned to his arms. They carried out a full-on affair, and she lost her virginity to her married ex-boyfriend. After Lindsay found out and divorced Dean, he and Rory continued to date until they realized they just weren’t in the same place in their lives, and it was all a waste of time. This led to Rory stealing a yacht and dropping out of Yale, thus beginning her downfall.
What happened to Dean Forester on ‘Gilmore Girls’?
His final appearance in the original series is kind of strange. In the Season 5 episode “Live and Let Diorama,” Dean shows up to help put together the new Stars Hollow museum and shares a tense moment with Luke (Scott Patterson) about how hard it is to date a Gilmore woman as a man who can’t offer her anything more than Stars Hollow. “This town, it’s all you are, and it’s not enough,” Dean tells Luke. “She’s gonna get bored, and you can’t take her anywhere. You’re here forever… You and me, same thing.” This is a little bit of nonsense given the fact that Dean moved to Stars Hollow from the gigantic city of Chicago just a few years earlier, but never mind that!
This bummer of a scene would have been Dean Forester’s final appearance ever, but he briefly shows up in the 2016 Netflix revival, Gilmore Girls: A Year in the Life. He reveals that he moved to Scranton and has three kids with his wife, Jenny.
One other notable thing about that last Gilmore Girls scene with Luke is that Dean’s outfit — a sturdy jacket over a plaid button-down — seems like a foreshadowing of the outfit Padalecki be wearing for every single episode on Supernatural.
What happened to Jared Padalecki after ‘Gilmore Girls’?
Just months after his final Gilmore Girls appearance, Padalecki debuted as Sam Winchester on Supernatural. He had to audition a few times and almost lost the role because, as he put it on Michael Rosenbaum’s “Inside of You” podcast, producers thought he was “stupid” — thanks, at least in part, to Dean Forester, who did not share Rory’s love for books and learning.
Padalecki went into the audition without a script, and decided he should be brooding and mysterious, like many TV hunks of the time. Later, he was told by his manager that he needed to “be more smart” because producers were looking for someone a little more academically gifted than the roles they had seen him play.
“I was on Gilmore Girls, and I was doing the whole brooding, like ‘Uh, I’m James Dean,’ because that’s what worked back in the day when you were auditioning,” he recalled. “And the critique came back to my manager, and it was like, well, [series creator Eric] Kripke’s looking for an intellect, like a David Duchovny type, which wasn’t directly saying, ‘We think Jared’s stupid.'”
Padalecki’s manager called back and explained that the actor actually was a National Merit Scholar who was on the debate team and only missed one math question on the SATs, and the rest is history.
He went on to play Sam Winchester for 15 years, the brains to brother Dean Winchester’s (Jensen Ackles) muscle. And honestly, Sam would have occasionally killed to be a guy with three kids and a wife living in Scranton.
Now, Padalecki stars in and executive produces the CW series Walker, which will eventually return for a fourth season.