Guest Stars Chris Chalk as Gary Cooper Adina Porter as Kendra James Chris Messina as Reese Lansing Marcia Gay Harden as Rebecca Halliday Grace Gummer as Hallie Shea B.J. Novak as Lucas Pruit Jimmi Simpson as Jack Spaniel Brian Howe as Barry Lasenthal Clea DuVall as Lilly Hart Keith Powell as Wyatt Geary Casey Sander as Judge Cedarman Talia Balsam as Toni Dodd Alexander Bedria as Priest Co Starring Margaret Judson as Tess Westin Thomas Matthews as Martin Stallworth Riley Voelkel as Jennifer "Jenna" Johnson Katie Boeck as Singer Maho Honda as Waitress Adrian Bustamante as Zachary Webber Susie Abraham as Mimi Tassler Sarah Benoit as Veteran Journalist