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|Topher Grace||Carter Duryea|
|Scarlett Johansson||Alex Foreman|
|Dennis Quaid||Dan Foreman|
|Marg Helgenberger||Ann Foremann|
|Clark Gregg||Mark Steckle|
|Philip Baker Hall||Eugene Kalb|
|Ty Burrell||Enrique Colon|
|Clark Gregg||Mark Steckle|
|Zena Grey||Jana Foreman|
|Remi Adefarasin||Director of Photography|
|Myron I. Kerstein||Editor|
|Stephen Trask||Original Music Composer|
|William Arnold||Production Design|
|David Smith||Set Decoration|
|Damien Rice||Original Music Composer|
|Sue Chan||Art Direction|
|Molly Maginnis||Costume Design|
|Myron I. Kerstein||Editing|
"He's rich, young and handsome. He's in love with you and he's your dad's boss."
Dan Foreman (Dennis Quaid) is a 51-year-old advertising executive and head of sales for Sports America, a major sports magazine. Happily married with two daughters, Dan faces a life-changing event when his magazine is bought out by Globecom, an international corporation that promotes the corporate concept of "synergy". After he is forced to fire several of his longtime colleagues, Dan is demoted and becomes the "wingman" of his new boss, Carter Duryea (Topher Grace), a 26-year-old business school prodigy. While Dan develops clients through handshake deals and relationships, Carter champions the corporate creed of synergy, cross-promoting the magazine with the cell phone division and "Krispity Krunch", a snack food also owned by Globecom.Dan and Carter are both facing challenges in their personal lives. Dan is supporting two daughters—16-year old Jana and 18-year-old Alex (Scarlett Johansson) who is preparing to enter college—and learns that his wife is pregnant with their third child. Meanwhile, Carter is dumped by his wife of seven months, and focuses all his energy on work. With Dan facing the financial realities of a mortgage, education costs, and a new child, and with Carter needing Dan's practical, real-life experience in the field of advertising, the two form an uneasy friendship.One day, Carter, who has been struggling with loneliness following the breakup of his marriage, invites himself to dinner at Dan's house, where he meets Dan's daughter Alex, and the two quickly form an attraction. Their initial friendship allows Carter to forget his loneliness, and Alex, who is now attending New York University, is able to escape her own loneliness and boredom. In the coming days, Carter and Alex spend time together and become romantically involved. Fearful of offending her father, they keep their relationship a secret for the time being.Their friendship, however, takes a turn for the worse when Dan discovers that Carter and Alex have been seeing each other, approaches them in a restaurant, and punches his boss in the face. The confrontation with her father convinces Alex to break off the relationship with Carter who is heartbroken. Soon after, faced with a major setback with a longtime client who is unimpressed with Carter's "synergy" and cross-promotional ideas, Carter relies on Dan's personal approach, which ends up saving the account. Later, when Globecom CEO Teddy K tells Carter to fire Dan, he refuses.Following another corporate shakeup, Sports America is sold off, Carter is let go, and Dan returns to his former position as head of sales. Having developed fatherly feelings toward Carter, he offers him a position in his new department as his "wingman", but Carter refuses, admitting he needs to take some time off and examine what he really wants to do in his life, and the two part friends.
DVD : 2005-05-10