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Gilmore Girls fans have many strong opinions about the romances of Rory (Alexis Bledel) and Lorelai Gilmore (Lauren Graham). One of Rory’s major affairs was with Dean (Jared Padelcki) in season 4. Dean was married at the time, but one season later, Gilmore Girls creator Amy Sherman-Palladino was proud to build off that story.

'Gilmore Girls' Rory actor Alexis Bledel answers questions on a Television Critics Association panel
Alexis Bledel | M. Caulfield/WireImage for The WB Television Network via Getty Images

Sherman-Palladino was on a Television Critics Association panel for Gilmore Girls in 2005. She acknowledged that Rory f***ed up (her words), but explained how that led to great Rory stories in Gilmore Girls Season 5.

Amy Sherman-Palladino: ‘Rory f***s up’ in ‘Gilmore Girls’ Season 4

Sherman-Palladino cited Rory and Dean’s affair in Gilmore Girls Season 4 as a mistake on Rory’s part. It was not, however, a mistake in Gilmore Girls storytelling. 

“The relationship with Dean and Rory, the angelic teen making a really big mistake, that’s great,” Sherman-Palladino said. “A kid like Rory, when she f***s up it should be huge, because she doesn’t do it that much. So I think that that really propelled us into a wonderful story arc this year.”

It also added some depth to Dean’s character.

“Dean, who was such a Boy Scout for so long, I think it’s kind of good that we took him down this road because he needed some more dimension,” Sherman-Palladino said. “We needed to know that there was something more to this guy than just ‘I’ll save your cat for you, ma’am,’ and climbing up a tree with some tuna.”

Lorelei’s mistakes echoed in the next generation

Sherman-Palladino pointed out that the entire premise of Gilmore Girls is predicated on the choices teenage Lorelei made. Rory didn’t make the same ones, but she made romantic choices indicative of teenagers trying to figure things out. 

“Everybody in life makes stupid choices,” Sherman-Palladino said. “I think that’s why life is fun, seriously. If everyone made the right choice, we’d all be very bored. Our show is based on a 16-year-old girl getting pregnant, you know. That’s kind of a dumb choice so we sort of figured we’d just go back to our roots. I don’t even think it’s stupid choices, I think it’s called life. When you’re young, you have to make stupid choices. Otherwise you’re already someone who has the life experience. So I don’t consider the choices that she makes necessarily stupid, just like that’s how you learn.”

‘Gilmore Girls’ presented Rory with plenty of bad boys

Prior to Dean, Gilmore Girls showed Rory navigate some other boys of Stars Hollow. Rory already knew enough to avoid them. 

I know we all love Chad [Michael Murray] and his shaved head, but she had no interest in Tristan. At the time, she had Dean, the Boy Scout on the white horse and the ‘Kill for you.’ What we like on Gilmore Girls is we like characters that have good and bad.  And all of our characters have to have good and bad, and they have to be flawed, or they’re uninteresting. A really sweet, darling Tony Soprano, nobody would watch. So in all of the boys that Rory has been attracted to, there has been good, and there has been bad. Jess had a lot of anger and a chip on his shoulder, but he was very intelligent. He was very, actually, loyal to her in his own way and he tried to fight his own demons to be with her. There were a lot of good things about him. There was a lot of bad that came along with it.

Amy Sherman-Palladino, 1/22/05
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Focusing on the good in that equation is what made Rory who she was on Gilmore Girls.

“Rory is someone who, we established from the very beginning, always was willing to see the good in people,” Sherman-Palladino said. “She’s a nonjudgmental gal. And at the time, she was looking for someone who could put that same sort of mental stimulus that she had: the books, the music, the world-life views that she wanted to talk about. So I didn’t consider Jess a bad boy. He was a bad boy who read, you know. He never got drunk, he didn’t shoot up, he read a book, and he was mean to Luke.”

Which brings Gilmore Girls Season 5 to Rory and Logan

“Now our new boy is a different kind of boy,” Sherman-Palladino said. “He’s also got good and bad. He’s got a wonderful, free spirit, and he’s got a love of life and also a great intelligence. And he’s got some flakiness that goes along with it.”