Guest Stars Kane Ritchotte as Benjy Fleming Amy Sedaris as Gail Fleming Melissa George as Jenna Ryan Betty Buckley as Cheryl Fleming Simon Templeman as Carl Sebastian 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 Jorge Luis Abreu as Salon Manager David Manis as Prosecutor David Doty as O'Dell Marc Vann as Hal Duncan Damara Reilly as Female Guard Wendy Schenker as Speed date #3 Gwen McGee as Judge Caryn West as Speed date #1