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A stockbroker attempts to win back the heart of his former high school girlfriend, but inadvertently sabotages himself by taking the advice of a tech-savvy coworker and attempting to trace her every move. Gary, Simon, and Cindy all work at the same firm. One day, while perusing his high school alumni webpage, Gary stumbles across the profile of his old girlfriend Jennifer. They haven't talked in twenty years, though as fate would have it Cindy and Jennifer are close friends. Jennifer is still single, and lately she's been looking for a change. After helping her secure a job at the firm, Gary admits that he would like to give their relationship a second chance. But Jennifer isn't sure she wants to settle down, and begins looking for love in all the wrong places. Meanwhile, Gary makes it his mission to win Jennifer back, even if it means hacking into her computer and cell phone and listening in on her voicemail. As Gary's obsession with Jennifer escalates, his actions become increasingly irrational and off-putting.