Ironically, it was Jared Padalecki, who plays Dean, who took the most Rory-esque approach to his preparation: Research, research, research. “I watched a few of those first seasons,” Padalecki says. “I wanted to see what my initial take was on the character. I tried to study who I was and who I wanted Dean to be. I really focused on seasons 2 and 3, not 4 and 5 as much because Dean was embroiled in controversies. I got to focus on the parts of Dean that I liked the most and thought stood the test of time.”
As far as the actors were concerned, the impact of their characters’ decision wasn’t the most difficult part of filming the scene. Rather, it was trying to fit both Bledel and Padalecki — who’s more than 6 feet tall — into Rory’s freakishly small bed.
“We brought Rory’s bed back [for the revival],” Sherman-Palladino says. “And I remember standing in that room saying, ‘There’s no f—ing way Jared and her fit in that bed.’”
Spoiler alert: They didn’t. “It was like a miniature twin,” Bledel adds. “In the outtakes I fell off that bed a couple of times.”
“We did have a joke about casting all of Alexis’ [real-life] boyfriends,” casting director Mara Casey reveals. “She dated Jared and Milo (Ventimiglia). And she also dated a young New York actor named Chris Heuisler, who played a guest role. Real sweet kid.”
The series had already fired two Deans when Rudofsky and Casey got started as casting directors. (Anthony says he had originally been conceived as a more “alternative” character; when the part changed, it had to be re-cast.) They weren’t even focused on finding a new Dean when a manager called, telling them they had to meet his client before he went back to Texas the next day.
“We said, ‘Well, we’re not auditioning that part yet,’” Rudofsky said. “He’s like, ‘I’m telling you, you have to meet this kid.’”
The two agreed, and soon enough, in walked Jared Padalecki—then 17, going on 18. And sure enough, he nailed it.
“We didn’t say anything to him,” Casey recalled. “We just gave the eye look, and asked him to step outside.”
With that, Rudofsky ran to Sherman-Palladino’s trailer and asked her to read Padalecki for the role before his flight back to Texas. She agreed, he read, and he left.
Then, Rudofsky said, Sherman-Palladino turned to her and Casey, and said, “Well, that’s not fair.” When they asked why, she said, “You can’t cast him on the first try.“
“She said, ‘It can’t be that easy; read more guys,’” Casey said.
And so, they did—but still, Padalecki landed the role.
EW reported Jared Padalecki, Milo Ventimiglia remember Jess and Dean's season 3 throwdown
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What many fans will remember about the scene is the fact that “bad boy Jess” had a bit of a disadvantage when fighting “sweet Dean,” and it wasn’t because Padalecki couldn’t physically feel anything. “I can’t remember if I was shooting the MacGyver pilot — whatever happened, I was injured,” Padalecki recalls. “I remember being on like four Advils every four hours and just not really feeling anything. And I remember Milo [Ventimiglia] going like, ‘This is kind of ridiculous because you’re twice my size and I’m holding my own.’”
And yet, the thing Ventimiglia remembers most is having to fight a friend. “Those are always funny moments to play when you have to get into a fist fight with someone that you absolutely adore,” he says. “It was a lot of Jared and I just making sure that A) we were safe, but B) it looked aggressive.”
