Guest Stars Sarah Hadland as Monica Draper Shobna Gulati as Vicky Paul Whitehouse as Marshall "Monty" Montgomery Ethan Lawrence as Ray Montgomery Layton Williams as Sam Steve Edge as Simon David Broughton-Davies as Bernard Rodger Jason Barnett as Phillip "Cappy" Caplan Olivia Nakintu as Julie Caplan Sabrina Sandhu as Stacey