Directed and written and narrated by Woody Allen, the film follows the life of Bobby Dorfman (played by Jesse Eisenberg), nephew of the great Phil Stern (played by Steve Carell), movie agent extraordinaire. Dorfman is a shy, awkward kid who dreams of a grand life in the big city of Hollywood. What befalls him instead is getting mixed up in an awkward, uncomfortable love triangle between his uncle, himself, and his uncle's secretary Vonnie (played by Kristen Stewart). While Vonnie is aware that she is seeing uncle and nephew, neither Stern nor Dorfman know that they are the other man in Vonnie's life.
When they both accidentally discover that they are both lovers of Vonnie, Dorfman and Stern give Vonnie an ultimatum, forcing her to choose one. Inevitably, she chooses Stern, and a defeated Dorfman abandons his dreams of fame and fortune in Hollywood and instead returns home to New York to work with his brother Ben (played by Corey Stoll). By night, Ben runs a nightclub, but by day, he's an infamous gangster, unbeknownst to Dorfman or the rest of his family.
With Dorfman's help, Ben's nightclub gains notoriety and excessive popularity, allowing Dorfman to mingle with the upper class, including beautiful Veronica Hayes (played by Blake Lively). Dorfman seems to instantaneously fall for Hayes' charm and looks, as the audience quickly catches the irony that her name is Veronica, just like Vonnie's full name. After a somewhat brief romance, Hayes reveals that she's pregnant, and she and Dorfman begin a marriage together to raise their child.
While Dorfman's life seems full of bliss, Ben's life takes a toll for the worse when he decides to help his sister Evelyn (played by Sari Lennick) with her unruly neighbor Joe (played by Brendan Burke) by killing him instead of just talking to him, as Evelyn asks. While Ben has been able to keep his gangster dealings a secret up to this point, he is caught and sent to prison over Joe's death, and eventually electrocuted for the murder.
In the meantime, Dorfman gets a surprise visit from his uncle Stern and Vonnie at his nightclub. While Stern and Vonnie seem happy and content in their new marriage, Vonnie still can't help but flirt with Dorfman, and Dorfman reciprocates, despite his happy marriage with Hayes. Dorfman and Vonnie agree to meet later and spend the next day together, which ends with them kissing on a New York bridge. However, that is as far as their relationship goes, and both return, somewhat reluctantly, to their spouses. Even though the day spent together was in secret, Hayes approaches Dorfman later to ask if he has cheated on her with Vonnie, as she had a dream that he did. Dorfman of course assures her that he did not, and Hayes seems appeased.
The film ends with Dorfman and Hayes, and Vonnie and Stern at separate New Year's Eve parties, both Dorfman and Vonnie nostalgic over their old romance.
While Woody Allen's film starts out with ample promise and excitement, both quickly drizzle into melancholy and lost dreams. The characters seem to accept their fate without a word, but still clearly long for something better, making the audience also long for something better. The redeeming quality of the movie is the time period Woody Allen was smart enough to set the story in; the 1930's setting provides terrific music, fashion, and an overall colorful feel to the story, but even the vibrancy of the time can't make up for the lack-luster and somewhat depressing tale.
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