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People: Alexis Bledel, Milo Ventimiglia. Milo Ventimiglia (2002-2006) Gilmore. Girls co-stars, Milo Ventimiglia and Alexis Bledel started dating in December 2002 after meeting on the set of television show Gilmore Girls. - Milo Ventimiglia's Dating History Who is Milo Ventimiglia Dating? . On Gilmore Girls, Rory Gilmore, played by Alexis Bledel dated. A trio of guys, but neither Dean nor Logan. Fanpop community Фан club for Alexis and Milo Фаны to share, discover content and connect .