Rory Gilmore’s had a pretty good life. She grew up in the ridiculously charming town of Stars Hollow, she has a fantastic relationship with her mother — better known as her best friend — and thanks to her mother’s love (and her grandparents’ financial support), she ended up going to Yale and chasing her dreams of becoming a journalist. And that’s not even mentioning the three hunks she dated along the way.
For Rory, it all started with Dean, the cute new guy from Chicago who would eventually evolve into a small town sweetheart. “I think he always felt like she was out of his league,” Jared Padalecki tells EW, describing how Dean viewed Rory. “She was smart and funny and quick and everybody loved her, but Dean felt like, ‘I can treat her right.’ He always felt like, ‘I wish I was good enough,’ so he tried to do things that helped convince himself that maybe he was good enough for her.”
Maybe that explains Dean building Rory a car, saying “I love you” first, or any number of the things he did to try to win her heart during his time on Gilmore Girls. But ultimately, Dean did win Rory’s heart … until season 2 introduced a new guy who had a leather jacket and a love of literature. Enter Jess Mariano.
“He was a little bit of trouble,” Milo Ventimiglia says of Jess. “He’s the guy that kept everyone on their toes.” But for Jess, Rory was the one who kept him on his toes. “You can be in front of the most beautiful person but if intellectually you’re not stimulated, the excitement behind the beauty may fade. Rory was, of course, a beautiful girl, but it was the mental sparring that kept him interested.”
Ventimiglia continues: “And as much as Jess was stimulated by Rory’s mind, Rory was stimulated by a guy who didn’t play by the rules — and yet he still had the intelligence.”
Jess’ only downfall was his inability to deal with certain situations. Translation: He ran. Whenever things got tough, Jess left. “He just didn’t quite have the emotional stability to handle a lot that was thrown his way,” Ventimiglia says.
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And that leads us to Rory’s third and final boyfriend of the series: Logan Huntzberger, the wealthy playboy who settled down for Rory. “Rory didn’t need anything from him,” Matt Czuchry says. “Rory was her own woman, and I think that’s what drew him in and made Logan want to give her everything.”
Yet, at the end of Gilmore’s seven-season run, Rory was single. Having just turned down a marriage proposal from Logan, she was off to pursue a career. But with Netflix’s Gilmore Girls: A Year in the Life just around the corner, could Rory get a happily ever after with one of her exes?
Well, they’re all set to appear, and the good news is that everyone seems to have grown up. “You think back to your first love and it really overtakes you, and I think [Dean] just never really got past that point,” Padalecki says. “But we see a more mature, 10-years-older Dean in the new Netflix series, and I was really happy with the man he turned out to be.”
Something similar can be said for boyfriend No. 2. “Jess ultimately grew up,” Ventimiglia says. “Where you pick back up with him, he’s only become a more refined version of the kid that used to be a troublemaker. He is more caring and caregiving than anything else.”
Then there’s Logan. “In the original series, I was happy that Rory said no to Logan because I feel like, at that particular time, it wasn’t right for Rory to get married to anybody, and it shows her strength and her independence, which has always been I think a very powerful theme of the show,” Czuchry says. “I love that ending for the original series.”
However, could things end on better terms for Logan and Rory in the revival? “In terms of where things are at the end of these four chapters for Logan and Rory, it’s pretty special. I’ll say that,” Czuchry says. “It’s very, very special.” Let the fan theories begin!
Gilmore Girls: A Year in the Life hits Netflix Friday, Nov. 25.