Brian doesn't believe in soul mates. Brian's best friend Edward, however, has the perfect girlfriend. After showing a cliché romantic comedy for "film night" at the Jersey City coffee shop where Brian works, everything gets turned upside down. Brian starts dating Ashley, a stand-up comedian and match made in cynical heaven, and Edward’s perfect girlfriend breaks up with him. Brian falls harder and harder for Ashley,but when she suddenly disappears without a trace, Brian enlists the help of his broken-hearted best friend and the imaginary characters from the cliché romantic comedy to find her, only to discover that her relationship status may be more complicated than it seemed.

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