Special Guest Stars Dan Bucatinsky as Rob Helen Hunt as Winnie Lindell Melissa Etheridge as Herself Guest Stars Jane Adams as Nina Daniels Michaela Watkins as Stacey Lauren Weedman as Mayor Jo Pezzimenti W. Earl Brown as Michael Schaeffer Merrill Markoe as Herself Tony Goldwyn as Bob Lipka Polly Draper as Diana Matt Bush as Clive Matthews Co Starring Matt Oberg as Brian Pile Danny Jolles as Nate Jasmine Ashanti as Samira Sandy Honig as Rose Holmes as Melanie Katy Sullivan as Carla Grover Whitmore as Gordon Gavin Matts as Eliot Robby Hoffman as Randi Jake Shane as Social Media Girlie Ingrid Haas as Margot Rosie McDonald as Ellie Shantell Yasmine Abeydeera as Makeup Person Colin Fitzmaurice as Stagehand Cyd Strittmatter as Elaine Spivak Jordi Caballero as Dr. Poghosyan
