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A man meets the perfect girl one night out in Chicago but loses her. On a quest to look for her during the week, he not only finds her, but finds out who he is in the process.
Brandon Tripper has always played things cautious, whether in life or love. One night he meets a fiery Australian named Zoey who may be his perfect women. However, at the end of the night they get split up without exchanging any information.
Having realized he screwed up, Brandon sets out to retrace his steps to all the bars he and Zoey went to over the course of the next week. Tagging along is his roommate, the successful entrepreneur Derek. He tries to break Brandon out of his cautious, introverted shell, believing that playing it safe prevents a person, like Brandon, from truly living. Also, Derek's seemingly carefree attitude towards women clashes with Brandon's hopeless romantic view of love.
The two make their way from bar to bar, having discussions on relationships and experiencing different situations, such as Derek, a Packers fan, drunkenly confronting Bears fans, a karaoke contest and a run-in with Brandon's ex-girlfriend Angela. Brandon finally realizes Derek is right and decides to take some risks, like finding a different job and finds it to be incredible. Derek also agrees with Brandon's approach towards love and vows to settle down when he finds the right one.
The two make their way to the last bar Brandon and Zoey went to. Derek finds the love of his life, the lovely Anna Kendrick, who is his celebrity crush. Meanwhile, Brandon finds Zoey and the spark they had continues like they had never separated, leading Brandon to fly down to Australia with Zoey for two weeks.