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Rory (Alexis Bledel) and Dean (Jared Padalecki), Gilmore Girls from Was It Good for You? TV's Most Memorable First Times Rory and Dean's high school romance was somewhat of a fairy tale. But although Rory lost her virginity to her first love, it wasn't the picture-perfect experience you'd predict. In the season four finale, the former couple reunited for their first time together—while Dean was married to Lindsay. Not a good look, you two.