Ventimiglia joined the Gilmore Girls cast in Season 2 to become the second of Rory's three great loves. Since the series ended in 2007 with Rory turning down Logan Huntzberger's (Matt Czuchry) proposal and Czuchry confirmed his return to Stars Hollow earlier this month, it seems probable that the Netflix four-part series will deal with who is actually the right guy for Rory (and end years of heated debate).