The film centers on a hooker-turned-Broadway-thespian (Imogen Poots) and follows the “recurring intersection between these two facets of her life”. A Broadway director (Owen Wilson) pays for her escort services despite being married to the star (Kathryn Hahn) of his new play A Grecian Evening. The play’s writer (Will Forte) falls for her as well, despite the fact that he’s already dating her therapist (Jennifer Aniston), whose alcoholic mother is in rehab.
The script was written by Peter Bogdanovich and ex-wife Louise Stratton, hoping to direct since 2005. In 2010, proteges of Bogdanovich – Wes Anderson and Noah Baumbach – offered their backing to get the film made, agreeing to serve as executive producers.
In 2012, when the film was officially announced, Owen Wilson, Brie Larson, and Olivia Wilde were signed on in lead roles. Larson was to play the prostitute turned actress and Wilde would play the role of her therapist. Jason Schwartzman was also rumored to be in negotiations to play Wilde's playwright boyfriend. Due to production delays, Owen Wilson is the only actor to remain with the project. In February 2013, it was announced that Jennifer Aniston would replace Olivia Wilde in the role of the therapist, the same time Kathryn Hahn, Cybil Shepard, and Eugene Levy were announced as cast members. Despite filming scenes since the start of filming, Imogene Poots and Will Forte were announced as taking roles of the prostitute and playwright July 23, 2013 and July 24, 2013. The same week, Joanna Lumley, Debie Mazar, Rhys Ifans, Lucy Punch, Ahna O'Reilly, Jake Hoffman as being cast in the film.