Writer Jeremy Catalino originally conceived of the story for Crash Pad (2017) after meeting a married woman online and having a weekend-long affair with her. He wondered what would happen if the woman's husband found out about the affair and came after him. As of the film's release, Catalino and the woman both live in Portland, OR and remain friends.
Director Kevin Tent and writer Jeremy Catalino got the idea to approach Domhnall Gleeson for the role of Stensland after they both watched Ex Machina (2014), in which Gleeson stars, on its opening weekend.
Dawson's Creek (1998) was not the TV show Stensland was obsessed with in early versions of the screenplay. It was Felicity (1998) and then Gilmore Girls (2000) until Sony Pictures Worldwide Acquisitions came aboard the project. Since Sony also produced Dawson's Creek (1998), the production was able to license the show easily and the script was rewritten.
In March, 2012, a table reading of the screenplay was held in Beverly Hills, CA. Rob Lowe read Grady, Adam Brody read Stensland, Thomas Middleditch read Lyle, Eliza Coupe read Hannah, and Ashley Jensen read Morgan.
Billy Ocean declined the opportunity to play himself in a dream sequence. Actor Julian Christopher was awarded the role instead.