An adaptation of a semi-autobiographical play by director-dramatist Neil Simon, the story conveys the coping and coupling of George, a recently widowed writer (played by James Caan), who is introduced by his press agent brother to Jennie, a just-divorced actress. Both are uncertain of whether to start dating so soon and George has recurring memories of his deceased wife. Jennie is portrayed by Simon's then-wife Marsha Mason, the inspiration for the character. Caan said he made the film to earn some money while preparing to direct the 1980 film Hide in Plain Sight.
George Schneider is an author living in New York City whose hours are occupied by his work, by softball games in the park and visits from his married brother Leo, a press agent who has been trying to introduce widower George to eligible women. George's emotions are still raw from the death of his wife, and he continues to be reminded of her.
George is given the phone number of a Jennie MacLaine, an actress Leo recently met through her friend Faye Medwick, and dials it accidentally while intending to call someone else. After an awkward exchange, he repeatedly phones Jennie to explain why he called, even though she makes it clear that she, too, has no interest in a blind date. George's persistence results in her accepting his proposal of a "five-minute" date, face-to-face. If that doesn't go well, he promises to leave her alone.
They meet at her apartment and immediately hit it off. Jennie is recently divorced from a professional football player. George asks her for a traditional date and she accepts. At dinner, he explains how Leo has set him up on a number of disastrous dates, so he now finds himself pleasantly surprised to be with someone like her.
Leo is pleased and so is Faye, whose own marriage is on the rocks. To their astonishment, George and Jennie decide to get married after knowing each other only a brief time. Leo feels his brother is going much too fast. Faye asks to use Jennie's apartment while the couple is away on their honeymoon.
An idyllic trip to the Caribbean follows and George and Jennie are very happy, at least until another tourist who recognizes him extends condolences about George's deceased wife. He immediately sinks into a depression that continues through their return to New York. At his home, Jennie's attempts to cheer up George are met with curt responses and insults. She returns to her own apartment to discover that Faye is having an affair there with Leo.
The marriage appears to be over almost as quickly as it began. George comes to his senses just in time, realizing how much he loves Jennie and how he doesn't want to lose her.
James Caan later called the film a "nothing. Although I do like working with Marsha. I needed the work. I had been working on Hide in Plain Sight for two years. I didn't have any money."
The film was a financial hit. It grossed $30 million at the domestic box office, making it the 27th highest grossing film of 1979.
Chapter Two, however, was not a critical success. It received mixed reviews from critics. Roger Ebert of the Chicago Sun-Times awarded the film 2 stars out of 4, writing "Chapter Two is called a comedy, maybe because that's what we expect from Neil Simon. It's not, although it has that comic subplot. It's a middlebrow, painfully earnest, overwritten exercise in pop sociology. I'm not exactly happy describing Neil Simon's semi-real-life in those terms, but then those are the terms in which he's chosen to present it. My notion is that Simon would have been wiser to imagine himself writing about another couple, and writing for another actress than his own wife; that way maybe he wouldn't have felt it so necessary to let both sides have the last word".
The film currently holds a 40% "Rotten" rating, with an average rating of 5/10, on the review aggregate website Rotten Tomatoes.
A portion of the 1977 play and the 1979 film was featured in the plot of "The Letter", a Season 3 episode of the American sitcom Seinfeld. In the episode, Jerry's artistic ex-girlfriend sends him a thoughtful letter trying to get him back. Later seeing a broadcast of Chapter Two on TV, Jerry realizes she copied the letter from the film word-for-word. In a deleted scene included with the DVD release of the episode, Jerry retaliates by breaking up with her using dialogue copied word-for-word from Plaza Suite, another Neil Simon film.