 He signed on for a spin-off of "Gilmore Girls" called "Windward Circle" which was to be focused on the relationship between Jess and his estranged father (played by Rob Estes), but the proposed series never made it to air.Afterward, he dropped down to a guest star/recurring cast member, and he came back for four episodes in season four and two episodes in season six.In the third and final season of "American Dreams", Ventimiglia played Chris Pierce, the rebellious boyfriend of Meg Pryor (Brittany Snow); Pierce and his single mother, Shelly (Daphne Zuniga), a Playboy bunny, move into the house next to the Pryors.