Handlung

New York City, 1995. Oliver "Ollie" Trinké (Ben Affleck) is a powerful media publicist who meets and quickly marries an attractive young Latina woman named Gertrude Steiney (Jennifer Lopez) and they are both very happy together. After about six or seven months, Gertrude discovers that she is pregnant, but Ollie, obsessed with his publicity work, neglects her in favor of his job and doesn't lighten his workload. On her due date, Gertrude does go into labor and Ollie forces himself to leave his office to be at the the hospital with her, but tragedy strikes when Gertrude dies from internal bleeding during childbirth.

To avoid his grief, Ollie buries himself in his work and spends long hours (day and night) at the office denying he is feeling any grief and ignores his newborn daughter, Gertie, while his widowed father, Bart (George Carlin), takes a month off from work at the Jersey City Sanitation Crew to care for her, but returns so that his son is forced to live up to his responsibility as a parent. Ollie is forced to take his baby daughter to work with him just when he must address a group of reporters. Under the stress of a botched diaper change and a baby who will not stop crying, Ollie trashes his latest client Will Smith, (who is late showing up for his soon-to-be released film Independence Day) in front of a large group of assembled reporters. The outburst costs him his job, so he moves out of New York and in with his father in New Jersey. He eventually apologizes for ignoring his daughter, and attributes his public outburst to his grief.

Seven years later in 2003, Ollie is still living in New Jersey with his father, Bart, and seven-year-old Gertie (Raquel Castro). When he goes to apply for a job at a local publcity firm, he finds that he is still blacklisted by all of New York's public relations firms who refuse to hire him despite his impressive job resume. Ollie has been forced to work as a civil servant in the Jersey City borough where he now lives (working as a garbage collector) alongside his father. Gertie, now in elementary school, often coaxes him to rent movies to watch as spending quality time together. At the video store, they meet Maya (Liv Tyler), one of the store's clerks, whose uninhibited probing into Ollie's love life almost leads to them having casual sex. She soon becomes a part of their lives.

As part of his job in the borough, Ollie speaks to a group of outraged citizens to win over their approval for a major public works project that will temporarily close a street in the neighborhood. His successful and enjoyable interaction with the crowd leads him to realize how much he misses the public relations work. He contacts Arthur (Jason Biggs), his one-time protégé, who sets up a promising interview at a promising firm who agree to meet with him.

The prospect of moving to New York creates tension among Ollie, Gertie, Bart, and Maya, especially when he says that his interview is on the same day as Gertie's school talent show. She yells at him, saying she hates him and that she wishes he had died instead of her mom. He claims he hates her right back, and says she and Gertrude took his life away and he just wants it back. He immediately regrets it and tries to apologize, but the damage is done and she pushes him away and runs to her room, crying.

A few days later he and Gertie apologize, and she accepts the fact that they will be moving to New York. While waiting to be interviewed at the office, he has a chance encounter with Will Smith (playing himself), the man he trashed at his public outburst years before. Smith has no idea who Ollie is, but their conversation about work and children makes him decide to sacrifice the former for the latter.

Ollie walks out of the office before he is interviewed and so is able to make it to Gertie's Sweeney Todd performance at the last moment. The film ends with him, Gertie, Bart, Maya, and the rest celebrating at the bar. He and Maya hint at possible feelings for each other before being interrupted by Gertie. He holds her and says that they are staying in New Jersey with Bart because he did not take the job in New York. She asks why he did so if he loved it so much. He says that he thought he did, but he loved his new life more because being a father to her was the only thing that he was ever really good at.