Chris Brander (Ryan Reynolds) has it all - money, good looks and a flashy job as an LA music executive. But things weren't always this way. In high school Chris was shy and overweight. The bright spot in his life was his friendship with Jamie Palamino (Amy Smart), the hottest girl in high school. The two best buds were inseparable. But Chris harbored a secret - he was hopelessly in love with Jamie. On the night of their graduation, Chris finally works up his courage and comes clean. A surprised Jamie tells Chris that she loves him too - like a brother. Then comes the dreaded 'Just Friends' speech. Angry and humiliated, Chris storms off. Ten years later, Chris has reinvented himself as a smooth talking lady killer, living large in Los Angeles. Chris's boss, KC (Stephen Root), has just given him his most challenging assignment yet - turning spoiled diva Samantha James (Anna Faris) into a pop-singing sensation. Wrangling the high-maintenance singer, who also happens to be his ex, seems a hellish task. But Chris's nightmare is just beginning. A plane malfunction, en route to Paris, causes Chris and Sam to make an unexpected pit-stop in New Jersey -- the first time Chris has been back home in 10 years. Chris drops in on his mom (Julie Hagerty) and smart-aleck brother, Mike (Christopher Marquette). Chris' plans to leave town are detoured when he runs into Jamie at a local bar. Suddenly faced with the chance to 'seal the deal' with the 'just friends' girl of his dreams, Chris postpones Paris. This sets off a chain of events in which Chris tries to woo Jamie, all the while distracting the suspicious Samantha. Unbelievably, Chris is finding it more difficult to romance Jamie than it was 10 years ago. The harder Chris tries, the further he slips into the 'friend zone.' When Dusty Dinkleman, (Chris Klein) another 'just friends' guy from high school shows up, Chris' fate seems doomed. Can he escape the 'friend zone?' Is it possible to go from 'just friend' to boyfriend?

  • 1 hr 34 minPG13
  • Nov 23, 2005
  • Romantic Comedy

Cast & Crew

  • Amy Smart

    Amy SmartActor

  • Ryan Reynolds

    Ryan ReynoldsActor

    Ryan Rodney Reynolds was born on October 23, 1976 in Vancouver, British Columbia, Canada, the youngest of four children. His father, James Chester Reynolds, was a food wholesaler, and his mother, Tamara Lee "Tammy" (Stewart), worked as a retail-store saleswoman. He has Irish and Scottish ancestry. Between 1991-93, Ryan appeared in Fifteen (1990), a Nickleodeon series taped in Florida with many other Canadian actors. After the series ended, he returned to Vancouver where he played in a series of forgettable television movies. He did small roles in Glenn Close's Serving in Silence: The Margarethe Cammermeyer Story (1995) and CBS's update of In Cold Blood (1996). However, his run of luck had led him to decide to quit acting. One night, he ran into fellow Vancouver actor and native Chris William Martin. Martin found Ryan rather despondent and told him to pack everything: they were going to head to Los Angeles, California. The two stayed in a cheap Los Angeles motel. On the first night of their stay, Reynolds' jeep was rolled downhill and stripped. For the next four months, Ryan drove it without doors. In 1997, he landed the role of Berg in Two Guys, a Girl and a Pizza Place (1998). Initially, the show was reviled by critics and seemed desperate for any type of ratings success. However, it was renewed for a second season but with a provision for a makeover by former Roseanne (1988) writer Kevin Abbott. The show became a minor success and has led to additional film roles for Ryan, most notably in the last-ever MGM film, a remake of The Amityville Horror (2005). Ryan was engaged to Canadian singer-songwriter Alanis Morissette, another Nickelodeon veteran, between 2004-2006. He has been married to Blake Lively since September 9, 2012. They have two children. He was previously married to Scarlett Johansson.
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  • Stephen Root

    Stephen RootActor

    Stephen Root, one of today's most prolific character actors, is currently starring in the HBO hit series Barry. The show has been nominated for multiple Emmy's and Golden Globes, earning a total of 32 nominations in its first season. Season two airs March 31st on HBO. In 2018, Stephen played a pivotal role in the AFI Film Festival winner On the Basis Sex (2018), the Ruth Bader Ginsberg biopic and starred opposite Melissa McCarthy in the New Line hit comedy Life of the Party. Reuniting with Joel & Ethan Coen and currently streaming on Netflix, Stephen is part of the talented ensemble in The Ballad of Buster Scruggs, which was nominated for an Academy Award. In 2017, Stephen was part of Jordan Peele's box office hit Get Out. Aside from his feature films, Stephen can also be seen in his recurring role on Amazon's hit drama series The Man in the High Castle (2015) as well as his starring role in HBO's comedy series Barry (2018). Root has earned rave reviews for bringing a variety of characters to life in such films as O Brother, Where Art Thou? (2000), Selma (2014), No Country for Old Men (2007), Leatherheads (2008), J. Edgar (2011), Cedar Rapids (2011) and Dodgeball: A True Underdog Story (2004). He was catapulted into the realm of cult hero when he starred as the put-upon Milton Waddams in Mike Judge's Office Space (1999). His animated features include Rango (2011), Finding Nemo (2003), Finding Dory (2016), Ice Age (2002) & Ice Age: The Melt Down (2006), and The Country Bears (2002). Root starred as the eccentric station owner, Jimmy James, for five seasons on NBC's NewsRadio (1995-99). Stephen has also recurred on FX's Justified (2010), Boardwalk Empire (2010), Turn: Washington's Spies (2014), Idiotsitter (2016), True Blood (2008), 24 (2001), West Wing (1999) and Pushing Daisies (2007). His many memorable guest appearances include Veep (2012), Angie Tribeca (2016), Fringe (2008), Raising Hope (2010), Children's Hospital (2010), CSI (2000) and Louie (2010). Root was the voice of Bill Dauterieve and Mr. Strickland on FOX's Emmy-winning hit animated series King of the Hill (1997) for an impressive 13 seasons. He has also lent his voice to a number of animated series including Adventure Time (2010), Gravity Falls (2012), American Dad (2005), The Cleveland Show (2009), DreamWorks' Dragons: Riders of Berk (2012), Kung Fu Panda: Legends of Awesomeness (2011), The X's (2005), and SyFy's Tripping the Rift (2004). Born in Sarasota, Root received his initial training in the BFA program at the University of Florida and remains a die-hard Gators fan. After three years of touring the U.S. and Canada with the National Shakespeare Company, Root settled in New York, honing his craft in many regional theaters and starring off-Broadway in Journey's End and The Au Pair Man. His Broadway debut came in So Long on Lonely Street, which was followed by the Tony award-winning production of All My Sons, with Richard Kiley. A starring role as Boolie in the Broadway national touring company of Driving Miss Daisy with Julie Harris, brought Root to Los Angeles where he currently resides.
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  • ANNA FARIS

    ANNA FARISActor

    Anna Kay Faris was born on November 29, 1976 in Baltimore, Maryland, to Karen (Bathurst), a special education teacher, and Jack Faris, a sociologist. She was raised in Edmonds, Washington. Her ancestry includes English, German, Scottish, French, Dutch, and Welsh. Anna started acting very young but not professionally. She loved watching theatrical plays and eventually produced one of her own with all the neighborhood children, in her immediate environment. She was always encouraged with the emphasis that she wasn't just "pretending" but rather being an unpaid producer, director, writer and an actress. Her first paid job was at the Seattle Repertory Theatre at age nine. She loved it and did other local plays and readings. After graduating from the University of Washington in English Literature, she decided to leave for London to work and write, but after filming (the less than wonderful) Lovers Lane (1999) and a short for the Seattle Film Festival, she decided to give Los Angeles a try. She signed up with a wonderful management agency and before she could catch her breath, Keenen Ivory Wayans cast her in heavy, hard, and comedic movie (To some people, it is almost too horrific.), Scary Movie (2000) and its sequels. She never takes anything for granted and just feels so very fortunate to have been given a chance. (An example was her trying to thank all the journalists and photographers that came to the New York premiere.) Anna was married to actor Chris Pratt in 2009. They have a son. They separated in 2017 and were divorced in November, 2018.
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  • Chris Klein

    Chris KleinActor

  • Roger Kumble

    Roger KumbleDirector

Cast & Crew photos provided by TMDb.