Stephanie Laing Director, Screenwriter, Producer Billy Magnussen Robert Actor Judy Greer Dorsey Actor Scott MacArthur Chad Actor Sam Richardson Actor Ann Dowd Judith Actor Margo Martindale Diane Actor Casey Wilson Katie Actor Henry Winkler Bobby Actor June Squibb Mabel Actor Elsie Fisher Cassie Actor Timothy Simons Bret Actor Jessica Miesel Taskrabbit Actor Rob Reiner Narrator Zoe Chao Actor Brad Morris Screenwriter Jonathan Tropper Producer Peter Odiorne Producer Alex Saks Producer Hassan R. Baqar Executive Producer David Eisenberg Executive Producer Dori A. Rath Executive Producer Patrick Somerville Executive Producer Larry Swets Executive Producer Kevin Atkinson Cinematographer Joe Klotz Film Editing Joseph Stephens Original Music Susie Mancini Production Design Ernesto Martinez Costume Design Sherry Thomas Casting