‘Gilmore Girls’: Who Is Rory’s Best Boyfriend? (POLL)

Rebecca Perlmutter September 27, 2025, 6:00 pm

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Jared Padalecki, Milo Ventimiglia, and Matt Czuchry as Dean, Jess, and Logan on Gilmore Girls — Everett Collection

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Our annual fall rewatch of Gilmore Girls is about to hit completely different because October marks the show’s 25th anniversary.

While there was only one man who fans hoped to see Lorelai Gilmore (Lauren Graham) with at the end of Gilmore Girls (Seriously, was anyone actually Team Christopher?), her daughter Rory (Alexis Bledel) had not one but three worthy love interests, sparking one of the greatest debates in TV romance history: Who is Rory’s best boyfriend?

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