Matthew Diamond Director Brooke Burns Tanya Actor Gregory Harrison Mr. Thompson Actor Nicole Paggi Daisy Actor Justin Baldoni Jake Actor Martha Anne Madison Sally Actor Nadège August Kimmy Actor Shashawnee Hall Henry Actor Jay Kenneth Johnson Chip Actor Kayla Mae Maloney Betsy Actor David Thomas Jenkins Robbie Actor Steven Eckholdt Cousin Eldridge Actor Dale Raoul Aunt Helen Actor John Sanderford Bosworth Actor Gregg Rossen Screenwriter Brian Sawyer Screenwriter Lincoln Lageson Producer Larry Levinson Executive Producer Amanda Phillips Atkins Executive Producer Maximo Munzi Cinematographer Jennifer Jean Cacavas Film Editing Lawrence Shragge Original Music Penny Perry Casting Amy Beth Reece Casting