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Two air traffic controllers who thrive on living dangerously compete to outdo each other on several levels.
When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.
Rich, successful Bryce meets beautiful Lissa at a bar one night and invites her back to his house, not suspecting for a moment that Lissa isn't really who she seems. What unfolds next is a dangerous, tangled web of double-crosses and seduction.