Joe Swanberg Director, Screenwriter, Producer, Film Editing Jake Johnson Tim Actor, Screenwriter, Producer Rosemarie DeWitt Lee Actor Orlando Bloom Ben Actor Brie Larson Max Actor Sam Rockwell Ray Actor Anna Kendrick Alicia Actor Mike Birbiglia Phil Actor Jane Adams Woman on Beach Actor Sam Elliott Pop Pop Actor Judith Light Grandma Actor Ron Livingston Bob Actor Melanie Lynskey Squiggy Actor Kent Osborne Actor Steve Berg Actor Jude Swanberg Actor Alicia Van Couvering Producer Ben Richardson Cinematographer Dan Romer Original Music