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 David Harbour as Elliot Hirsch Constance Zimmer as Taylor Warren Salli Richardson-Whitfield as Jane Barrow Lauren Tom as Kathy Ling Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Thomas Matthews as Martin Stallworth Trieu Tran as Joey Phan Charlie Weirauch as Jake Watson Wynn Everett as Tamara Hart Riley Voelkel as Jennifer "Jenna" Johnson Brian Henderson as Connor