Plot
Set in the corporate dominance of the working world, Dan Foreman is a 51-year-old advertising executive and head of sales for Sports America, a major sports magazine. Happily married with two daughters, 16-year-old Jana and 18-year-old Alex, who is preparing to enter college, Dan suddenly faces an unexpected life-changing event when his magazine is bought out by Globecom, an international corporation that promotes the corporate concept of “synergy”.
After Dan is forced to fire several of his longtime colleagues, he is demoted and becomes the “wingman” of his new boss, Carter Duryea, 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 his two daughters and learns that his wife is pregnant with their third child; meanwhile, Carter is dumped by his adulterous, narcissistic wife of seven months and focuses all of his energy on work. With Dan facing the financial realities of taking out a second mortgage to cover his daughter's college education costs and a new child, and with Carter needing Dan's practical, real-life experience in the field of advertising, the two characters form an uneasy friendship.
Carter, who has been struggling with loneliness following the breakup of his marriage, invites himself to dinner at Dan's, where he meets Alex, and there is an immediate attraction. Their initial friendship allows Carter to forget his loneliness, and Alex—now attending NYU—is able to escape her loneliness and boredom. In the coming days, Carter and Alex become romantically involved. Fearful of offending her father, they keep their relationship a secret.
However, the relationship takes a turn for the worse when Dan discovers that Carter and Alex have been seeing each other. He approaches them in a restaurant and punches his boss in the face. The confrontation with her father convinces Alex to break up with Carter, who is heartbroken. Soon after, Globecom CEO Teddy K visits the sales office; during a grand speech to all the employees on synergy and other similar corporate business strategies, he is questioned by Dan and shrugs him off.
Carter's boss, Mark Steckle, tells Carter to fire Dan. He refuses, claiming that losing Dan will cost them a major advertising contract. Steckle gives them 24 hours to seal the contract or be fired. As Dan has developed a long-term relationship with the client, Eugene Kalib, Carter gives way to Dan's personal approach. The strategy works, and they conclude a deal.
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 towards Carter, Dan offers him a position in his new department as his “wingman”, but he declines, saying he needs to take some time and discover what he really wants to do in his life.
On his way out of the building, Carter runs into Alex, and they exchange pleasantries. Dan's wife gives birth to a girl. He calls Carter—who is jogging outdoors for the first time and feels like a new man—in Los Angeles with the news.
