Gere was interested in the script, but Farino wanted only Hugh Laurie to play the role of David because he had "that innate decency that could carry this thing". On February 8, 2010, Laurie was reported to be in talks to play his first feature lead role. Leighton Meester and Mila Kunis were also said to join the cast as his love interest. On February 28, it was confirmed that Meester had won the role over Kunis, while Adam Brody, Alia Shawkat, Catherine Keener and Allison Janney were all in negotiations. Meester and Laurie had previously worked together when she guest-starred in two episodes of House, which had plot developments somewhat similar to the storyline of The Oranges. In the 2006 House episode "Lines in the Sand", Meester's character is a 17-year-old who relentlessly pursues Laurie's "Dr. House" character, flirting with him and insisting that they should have sex— he eventually diagnoses that a fungal spore in her brain has resulted in her loss of inhibition and judgement. Farino knew Meester from Entourage where he directed her in the show's first season. He approached her while she was in the dressing room, preparing for a Gossip Girl episode shooting, and they made a "rushed audition". About her role, Meester said: "It’s a complete 180-degree turn from anything I’ve ever done. This fulfills something within myself that I could never find in my series [Gossip Girl]." Even though Alia Shawkat's name was the first mentioned by the casting director, Farino met with a lot of actresses for the role of Vanessa. Shawkat met Farino a year before she auditioned where he told her that they were considering Elliot Page for the part. After Page turned it down, Shawkat auditioned twice and was cast. Allison Janney and Oliver Platt had also worked together before in the television series The West Wing, while Catherine Keener and Platt had starred in the movie Please Give. Filming The ending was rewritten before shooting. During filming, Laurie, Meester, Janney, Platt, and Brody shared a house together. While the film is set in the fall, from Thanksgiving to Christmas in New Jersey, principal filmography started at the end of March 2010 in the upscale Beechmont section of New Rochelle in Westchester County, New York and lasted 29 days. Scenes were also shot in the neighboring Westchester communities of Mamaroneck and Bronxville, as well as the Tropicana Casino