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One Winter Weekendâs cast includes Taylor Cole, Rukiya Bernard, Dewshane Williams, and Jack Turner. One Winter Weekendâs Cast Taylor Cole as Cara. Taylor Cole is best known for her regular roles in television series The Event and Summerland.
Cast. 1  Breckin Meyer as Josh Parker. 2  Seann William Scott as E.L. Faldt. 3  Paulo Costanzo as Rubin Carver.  DJ Qualls as Kyle 1  Edwards. Amy Smart as Beth Wagner.  Tom Green as Barry Manilow, the college tour guide and narrator of the 1  film. Rachel Blanchard as Tiffany Henderson, Josh's long distance girlfriend.  Anthony Rapp as Jacob Schultz.