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 Spencer Achtymichuk as Charlie Brett Kelly as Francis Bischetti Laara Sadiq as Mrs. Brody Julia Tortolano as Sara Steve Archer as Club Manager Allison Warnyca as Missy Tyler McClendon as Waiter Dale Hall as Mr. Parker Alesia Dicicco as Jessie Aeja Goldsmith as Tanya Robbie Holloway as Bernie Ty Hill as Kid