When sitting down with Michelle Pfeiffer to discuss the character of Lillian, Alex Kurtzman decided on a more naturalistic, slightly disheveled look for the role. As he described it: "this woman probably hasn't put on make-up in a year. She's been sitting by her dying husband's side and when we first meet her in the movie, that's where she's at. If we're too glamorous in this portrayal, it'll ring totally false." Pfeiffer agreed wholeheartedly and altered her otherwise glamorous image to play the grieving widow.
Michelle Pfeiffer tried to get a scene removed where her character slaps Chris Pine across the face. Pfeiffer felt that it would be difficult for her character to redeem herself in the eyes of the audience. However, the scene remains in the film.
Alex Kurtzman spent two weeks prior to principal photography rehearsing with the entire cast; a practice rarely done for a Hollywood movie.
The screenplay for this film was featured in the 2010 Blacklist; a list of the "most liked" unmade scripts of the year.
Rachel McAdams was considered for the lead role, but Elizabeth Banks was later cast.
Hilary Swank read the script and pursued a role in the film, but was ultimately turned down.
Amy Adams was considered for the lead role but dropped out to spend time with her family.
Post production was temporarily delayed while additional scenes featuring Michelle Pfeiffer, Chris Pine and Olivia Wilde could be shot in Los Angeles in July 2011.