Top Hollywood talent agent Jack Giamoro (Ben Affleck) seems to have it all: a successful career, a lot of money, a nice car, a beautiful wife, etc. However, while pursuing success, he somehow lost himself and neglected his marriage. He decides to take a journal writing class to do some self-searching. The class is taught by Dr Primkin (John Cleese). Jack has been married to Nina for 4 years and they live together in Malibu, California. Jack's father Ben (Howard Hesseman) stays with them, and he used to be a movie producer in the 1960's. 6 months ago he had a stroke.Jack specializes in handling TV writers. Jack is a partner at his agency with colleagues Arlene (Gina Gershon), Alan (Kal Penn) and Morty (Mike Binder). Jack is under pressure to sign writer David Lilly (Jerry O'Connell) as that would bring a lot of commission to the agency. Lucky (Damien Wayans) is Jack's assistant at the agency.Gradually, Dr Primkin wants his class to write deeper passages in their diary, including a secret that nobody knows. Jack fails to sign David, who passes on Jack, and suddenly Jack realizes that his client Phil Balow (Adam Goldberg) has not returned his calls for 3 weeks. Jack visits Phil on the sets of his TV show, prompting Phil to set up a meeting with Jack the following morning. Jack believes that Phil wants to leave the agency. That night Nina tells Jack that she slept with Phil. Nina was a super model whom Jack met when he attended a photo-shoot with Morty 5 years ago.Jack's seemingly perfect world starts to unravel when he learns that his wife, Nina (Rebecca Romijn), is cheating on him with his most important client. Jack tells his colleagues that Phil has been sleeping with Nina. Jack wants to drop Phil, but he is worth 10's of millions of dollars to the agency. The partners want Jack to try and find a way to move past this. Jack throws Nina out of the house. He remembers a time back when he was in school. Jack had a crush on a girl named Leah and spent time with her, only to find that she had a crush on his brother Anthony. This was the only reason Leah hung around with Jack. Jack complained to his parents. Ben never cared, but his mother was livid and took Anthony to confront Leah and her parents. Anthony was killed in an accident that night.Things get worse when Barbi (Bai Ling), an ambitious journalist, steals Jack's journal, which contains secrets that could ruin him personally and professionally. Babri is in the same journal writing class as Jack. Barbi had written a piece in the papers on Jack kicking out Nina. Lucky finds that Babri has been contracted to wrote 5 articles on Jack's rise in Hollywood and how he stole clients. Lucky also finds that Barbi had sent 5 scripts to the agency and was rejected every time.Jack and his fellow partners worked at the mail-room of a different agency. They stole all the clients and formed their own group. Also, they stole all the secrets, just in case the agency ever came after them, then they would have leverage. 10 years later, Jack and his partners become successful and are sued by their former employers. But Jack wins the case in court.Barbi sends her boyfriend to Jack's home, who attacks Jack (while wearing a mask) and Jack ends up in the hospital with broken teeth. Nina comes back to take care of Jack and Ben, while Jack is undergoing extensive dental work. When Jack returns to work and realizes that the journal is missing and that it was stolen during the attack.Barbi calls Jack and reveals that she has his journal. Jack is livid and he had seen the face of his attacker and remembered him as one of guys named Jimmy who helped him move out Nina's stuff out of the house. Jack drives over to his house and assaults him with a baseball bat. Jimmy refuses to return the journal to Jack. Jack is forced to fight for everything he has worked so hard to achieve and in doing so, he attains the self-insight he was looking for. Jack meets Barbi for dinner in Chinatown and asks for the journal back. When Barbi refuses, Jack snatches the journal from her purse and makes a run for it. Jack's partners were watching over him and run with him. Barbi corners Jack and his partners in the main market. Jack manages to escape but drops the journal.Jack drives over to David's and makes a passionate plea to sign him. David agrees. The partners confront Jack and realize that the journal contains private information that directly contradicts their testimony at the trial. The partners try to buy the journal from Barbi and to get her to kill the story, but she refuses. Jack fires as assistant at the agency who had recommended Jimmy to him to move Nina's stuff.Jack realizes that he had no right to blame Nina for what happened with Phil. Jack realizes that as he got engrossed in his work, Nina loved him no matter what. Nina reaches out to Jack at the agency and apologizes for what she did.Nina walks out of the agency and runs into Barbi, who wants an exclusive with Nina. Nina lures Barbi into the agency conference room for her interview. Nina gets Arlene to inform Jack that she has Barbi. But Jack is auditioning David's wife, who is part of David's deal with the agency.Nina snatches the journal from Barbi and locks herself in the conference room closet and calls Jack. Jack manages to finish the audition with David's wife and heads to the conference room to rescue Nina, but runs into Phil, whom he had been avoiding. Jack forgives Phil and realizes that everyone is imperfect. As Jack rescues Nina, David walks out of the agency, and Jimmy arrives to set fire to it. Jack asks Barbi to bury the hatchet and to get Jimmy under control, else they both go to prison for 10 years. Jack then follows Nina and makes up with her. Jack leaves the agency and Arlene replaces her.