Gilmore Girls costars Alexis Bledel and Milo Ventimiglia shared a romance both on and off the small screen. The pair portrayed Rory Gilmore and Jess Mariano, respectively, on the beloved 2000s series. Their characters dated on and off throughout the show, and in the real world, the actors were together for four years before splitting in 2006. Bledel eventually went on to marry Mad Men costar Vincent Kartheiser in 2014. Three years later, when she was up for an Emmy for her work on The Handmaid's Tale, the This Is Us hunk proved the old pals were still on good terms.