Guest Stars Kane Ritchotte as Benjy Fleming Amy Sedaris as Gail Fleming Melissa George as Jenna Ryan Simon Templeman as Carl Sebastian Jorge Luis Abreu as Salon Manager Marc Vann as Hal Duncan Betty Buckley as Cheryl Fleming Susan Chuang as Kathleen Lisa Long as Speed date #4 Victoria Hoffman as Speed date #5 Meredith Morton as Flora Mark Phinney as Doorman Light Eternity as Speed date #2 Jeffrey Scott Kelly as Elton Kerry Michaels as Older Actress David Manis as Prosecutor David Doty as O'Dell Damara Reilly as Female Guard Wendy Schenker as Speed date #3 Gwen McGee as Judge Caryn West as Speed date #1