Guest Stars Chris Chalk as Gary Cooper Adina Porter as Kendra James Chris Messina as Reese Lansing Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Trieu Tran as Joey Phan Thomas Matthews as Martin Stallworth Charlie Weirauch as Jake Watson Wynn Everett as Tamara Hart Chasty Ballesteros as Tea Megan Park as Gwen Valley Marshall Bell as Ross Fernholm Paul Willson as Dr. Dwayne Sotter Alexandra Rodriguez as Corrine Cornell Womack as Daniel Mendoza Norma Maldonado as Housekeeper Chauncey Jenkins as Karaoke #2 Monika Smith as Amy Stephanie Malouf as Karaoke #1