Guest Stars Dominic Burgess as Jerry Summers Molly Griggs as Wendy Young Laila Robins as Amy Piel Kelsey Grammer as Dr. Geoffrey Skadden Dashiell Eaves as Stan Novak Ajay Naidu as Dr. Sasani Medina Senghore as Kayla Gibson Michael Genet as Dr. Lockett Co Starring Kyle Fox Douglas as Skadden Assistant Katya Stepanov as Dr. Katya Melnikov Michael Levi Harris as Dr. Ilya Burkov Christine Pedi as Elaine Johnson Brit Whittle as Dr. Andrew Phipps Mac Brydon as Patron Catrina Ganey as Mrs. Demmings Dexter McKinney as Banker #2 Stephen Dexter as Banker #1 Alexandra Lemus as Student Faith Taylor as Anna