Eighteen years after Gilmore Girls wrapped and nearly a decade after Gilmore Girls: A Year in the Life, the question of who was “the one” for Rory Gilmore is still fueling passionate debate. Now, two stars at the center of the fandom’s most enduring love triangle—Jared Padalecki (Dean) and Matt Czuchry (Logan)—are revisiting the topic in a candid new conversation, and their answers might surprise even the most committed Team Dean, Team Jess, and Team Logan supporters.
Speaking with PEOPLE, the pair addressed the age-old question head-on. While both actors acknowledge that none of Rory’s relationships were perfect, they offered thoughtful, character-driven reasoning about where they land today—nearly two decades removed from Stars Hollow.
Jared Padalecki Surprises With A Team Jess Pick
Padalecki, who played Rory’s first boyfriend Dean, didn’t hesitate to back a different ex: Jess Mariano. “Funny enough, I’m team Jess […] Just knowing the show and having some idea of where Rory was in her life. They all were flawed, let’s be clear,” he said. “Well, I’ll say Dean was flawed. They all had their issues. But today, I’m team Jess.”
The nod to Jess will register as a twist for viewers who remember the early-series dynamics: Dean was the safe first love, Jess the rebellious intellectual match, and Logan the charismatic, complicated late-series partner. Padalecki’s comment underscores how time and perspective can shift allegiances, even for the actors who originally played these roles.
It’s also a notably self-aware take from Padalecki, who openly acknowledges Dean’s shortcomings while crediting the broader tapestry of Rory’s evolution. In a show built on sharp dialogue and deeply human choices, it makes sense that “the one” can look different with hindsight—especially when considering where Rory was in her life during each relationship.
Matt Czuchry Outlines What It Would Take For Logan
Czuchry’s answer is more conditional—and rooted in growth. “Yeah, it’s kinda changed for me over the course of time,” he shared. “I think right now […] if Logan does get married to his fiancée, that happens there, and let’s say they get divorced or something like that, and he changes his life, then I could see Logan coming back and being with Rory, because he would be in a completely different place in his life.”
It’s a measured view that recognizes Logan’s arc and the realities of timing. Czuchry stressed that it would take meaningful change to believably bring the pair back together. As he put it, “[Logan] wasn’t willing, basically, to give up that life that he had with taking over the paper. But I think if he went on and lived, sort of, that life, and had his wife, but then things change […] it just kind of depends on when we drop back in in the story, I think.”
Czuchry also made clear that any hypothetical reunion wouldn’t be a one-sided decision. “I don’t know how Rory would feel–maybe she would say no,” he said, drawing a laugh from Padalecki. What’s never changed, he explained, is why Logan fell for Rory in the first place: her authenticity and independence. “But I do feel like, for Logan, Rory always felt like she didn’t need any of the money. She didn’t need any of the attention. She didn’t need that lifestyle, and that was incredibly attractive to Logan because she was down-to-earth, and that’s what made her just so so special, and I think that Logan craved that.”
By framing Logan’s future through the lens of personal growth and timing, Czuchry adds nuance to a character often debated for his privilege and choices. It’s a reminder that Gilmore Girls consistently balanced fantasy with consequences—especially in matters of the heart.
Why The Conversation Still Resonates With Fans
Part of what keeps the “Who is Rory’s one?” discourse alive is how well the series captured different phases of young adulthood: first loves, bad timing, and the friction between ambition and stability. Padalecki’s and Czuchry’s reflections tap directly into that longevity, offering perspectives that feel both honest to their characters and considerate of where the story left off.
Fans quickly latched onto their thoughtful answers. “It’s really fun that they still play along, and that they give thoughtful answers about what they think the characters might be up to,” one viewer commented. Another added, “Love this! If I am reading between the lines, this conversation is suggesting another mini series is needed. Let’s do this!”
Even without new episodes on the horizon, discussions like this keep Stars Hollow buzzing. They invite viewers to revisit the relationships not just as “teams,” but as evolving reflections of Rory’s growth—and the lessons that came with it. Whether you’re cheering for Dean’s earnestness, Jess’s literary spark, or Logan’s charm and potential, the latest round of insight from Padalecki and Czuchry proves there’s still plenty to unpack.
For now, the actors’ own loyalties say a lot. Padalecki’s unexpected shoutout to Jess acknowledges the character’s compatibility with Rory at key moments in her life, while Czuchry’s conditional case for Logan emphasizes maturity and self-awareness as the missing pieces. It’s a fitting snapshot of why this debate endures: there’s no simple answer, just a series of choices that felt right—or wrong—depending on when we drop back into the story.
Nearly two decades later, Gilmore Girls remains a conversation starter because it never treated romance as a destination. It treated it as part of the journey. And as Padalecki and Czuchry remind us, that journey still has fans—and even its stars—thinking about what comes next for Rory Gilmore.
