Guest Stars Britt McKillip as Reggie Lass Robin Dunne as Thomas "Trip" Hesberg III Barbara Barrie as Grandma Phyllis Tom Butler as Thomas Hesburgh, Jr. Co Starring Patricia Idlette as Kiffany Brett Kelly as Francis Bischetti Spencer Achtymichuk as Charlie Laara Sadiq as Mrs. Brody Julia Tortolano as Sara Allison Warnyca as Missy Tyler McClendon as Waiter Steve Archer as Club Manager Dale Hall as Mr. Parker Alesia Dicicco as Jessie Aeja Goldsmith as Tanya Robbie Holloway as Bernie Ty Hill as Kid