Claim: Richard Jenkins was featured in Friends with Benefits.

Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck , and starring Justin Timberlake and Mila Kunis in the lead roles . The film features Patricia Clarkson , Jenna Elfman , Bryan Greenberg , Nolan Gould , Richard Jenkins , and Woody Harrelson in supporting roles . The plot revolves around Dylan Harper -LRB- Timberlake -RRB- and Jamie Rellis -LRB- Kunis -RRB- , who meet in New York City , and naively believe adding sex to their friendship will not lead to complications . Over time , they begin to develop deep mutual feelings for each other , only to deny it each time they are together .   Principal casting for Friends with Benefits took place over a three-month period from April to July 2010 . Gluck reworked the original script and plot shortly after casting Timberlake and Kunis . Filming began in New York City on July 20 , 2010 , and concluded in Los Angeles in September 2010 . The film was distributed by Screen Gems and was released in North America on July 22 , 2011 . Friends with Benefits was generally well received by film critics , most of whom praised the chemistry between the lead actors . The film became a commercial success at the box office , grossing over $ 150.4 million worldwide , against a budget of $ 35 million . It was nominated for two People 's Choice Awards -- Favorite Comedy Movie , and Favorite Comedic Movie Actress -LRB- Kunis -RRB- -- and two Teen Choice Awards for Timberlake and Kunis .