Plot

A guy fed up with his job and married to a cheating wife reluctantly mentors a rebellious teen.

Bill is unhappy: he has married a banker's daughter and has a dead end job at the bank; his wife Jess is tied to daddy's wallet; and, Bill is developing a gut from lack of exercise and constantly eating candy bars. He dreams of buying a donut franchise to be independent of Jess's dad. Bill is roped into a mentoring program at his old prep school, assigned a smart-mouthed kid who pops up when least expected. When Jess starts an affair with Chip, a local TV personality and vain Rob Lowe look-alike, it sends Bill, the kid, and a young sales clerk from a lingerie shop on a quest to win back Jess and get the donuts. What about self-respect?—<jhailey@hotmail.com>

The story revolves around Bill (Aaron Eckhart), an overweight, middle-aged man dissatisfied with himself and his life. He works at his father-in-law, Mr. Jacoby's (Holmes Osborne) bank. But his job is meaningless with a made-up title, and his in-laws don't take him seriously, especially his brother-in-law. Jacoby is a pillar in the community and is considering a mayoral run. Bill and Jess, his wife (Elizabeth Banks) live in a house provided by her father and lead a comfortable lifestyle provided by him. Bill is trying to purchase a doughnut franchise with the Whitmans (Jason Sudeikis & Kristin Wiig), a friendly married couple who own the franchise business. Bill's interest in purchasing a franchise is an attempt to wean himself and his wife off Jacoby's finances.

At a public donation sponsored by his in-laws, Bill first meets "the Kid" (Logan Lerman), a spunky and easygoing teenager, who is running from the school principal. In the hallway, after the principal suggests a school mentoring program, he sees his wife talking with Chip Johnson (Timothy Olyphant), the local, pompous newscaster. Bill begins to get mildly suspicious, and meanwhile begins to "mentor" the Kid. Before a hunting trip with his in-laws and their pupils, he places a hidden camera in his and his wife's bedroom, and upon arrival discovers that his wife is having an affair with Chip. In a rage, he shows her the camera, and the two have an argument, bringing Jess to go to Chip and tell him about the tape, and Bill ends up beating him up. An online video later circulates of the tape and is passed around the staff at the bank, furthering Bill and Jess' embarrassment, particularly when Jess makes some offensive comments to Chip about Bill, their sex life and his penis size. Jess fears the video could ruin her father's chances for mayor and tries to conceal the news of her affair and the video from him.

Bill becomes well-known as Chip's "deranged fan", frequently having random people yell "Apologize!" at him throughout the film, a reference to him punching Chip and asking Chip to "Apologize!" while on the air. Bill begins to live with Sargeant (Craig Bierko), his successful younger brother. Sargeant's boyfriend Paul (Reed Diamond) encourages Bill to take up swimming, an early pastime of Bill's, which he starts to do to clear his mind. He continues mentoring the Kid, who senses the best in Bill, and devises a plan to win back Bill's wife. Introducing the lingerie salesgirl Lucy (Jessica Alba), he makes it seem as if Lucy and Bill are romantically involved, a plot in order to get Jess jealous. Meanwhile, Bill is still trying to get a doughnut franchise, but since the presence of Jess is required, they have Lucy act as Bill's wife.

Bill slowly begins to get a hand on his life again, cutting his addiction to sweets, losing weight, swimming daily, mentoring the Kid, and trying to win back his wife. At a family dinner, Bill volunteers to buy the fireworks for the 'club picnic' where his father-in-law intends to announce that he is running for Mayor. After a party with the Kid, Lucy and her friend, Bill attends the picnic at the golf course. At the picnic, Bill gets close to his wife and Chip. Chip promptly has security throw Bill out of the picnic, which the Whitmans witness.

Bill tells the kid to meet him at the back entrance, and while driving his car to the back of the golf course, he gets into an automobile accident, causing the fireworks to explode early. The Kid comes on a golfing cart, takes Bill to the hospital, where Jess shows up, and tells her husband that she's aware of his attempt to purchase the franchise. They end up discussing their marriage, which Bill finally reveals his unhappiness and their dependence on her father's money by stating "Our lives suck". After making vague decisions, Bill goes home and stares into a mirror. Seeing what his life has become, he cuts his hair (which he repeatedly says he despises throughout the film) and changes his wardrobe. He later visits Jacoby at his office and passes in his resignation, pointing out the obvious that he doesn't fit in with the company and he doesn't belong there, which his father-in-law understands and accepts his resignation. In a surprising out of character moment, Jacoby commends Bill for attacking Chip, given that he would've done the same if he were in that situation. Despite his daughter's attempt to conceal the news, it's implied that Jacoby knew about it long before, potentially when the online video circulates around the bank.

Bill goes to meet with the Whitmans and is surprised to see Jess, who is speaking as his wife to clear up their misunderstandings. Jess convinces them to let the couple buy the franchise. But during a private conversation, Bill reveals that he was going to call off the deal. But he has a change of heart and lets the purchase go through, with Jess keeping the business. They then reconcile their differences and mutually agree to go their separate ways, eventually putting their house up for sale.

The film ends with Bill coming to the Kid's school to say goodbye, as he's excited to start a new, unknown chapter in his life and move away. As he says goodbye with the promise to keep in touch, he tells the Kid to look in his locker. After doing so, his locker explodes with fireworks, much to the Kid's surprise and delight.