In 1985
Cumberland, Rhode Island, 16-year-old high school student Ted Stroehmann is about to go on a prom date with his dream girl, Mary Jensen, when he gets his
scrotum stuck in his zipper. He is hospitalized after managing to painfully unzip it, which causes him to miss their date. Ted subsequently loses contact with her. 13 years later, Ted is a magazine writer and still in love with Mary. On the advice of his best friend, Dom Woganowski, Ted hires
private investigator Pat Healy to track her down. Pat discovers that she is an
orthopedic surgeon living in
Miami with her
intellectually disabled brother Warren and roommate, Magda. After observing her for a few days, Pat also becomes fixated on her. He returns to Providence and lies to Ted about Mary, telling him she is overweight and has four kids by three different men. Pat quits his job and returns to Miami to pursue her. He resorts to lying and stalking to win Mary over. Meanwhile, Ted finds out that Pat was lying about Mary and drives to Florida to see her. During the drive, he picks up a
hitchhiker who leaves a dead body in his car. Ted is mistakenly arrested for the murder and bailed out by Dom after the hitchhiker confesses to being the killer. Pat and Mary spend several weeks dating, but she ends their relationship after her British architect friend Tucker slanders Pat with false stories of being a career criminal and suspected
serial killer. Angered over this, Pat confronts him and discovers Tucker is actually an American pizza delivery boy named Norm Phipps, who is also infatuated with Mary. Years earlier, Norm deliberately injured himself in order to become her patient and get close to her. He pretends to still be disabled to stay close and drive away other potential love interests. When Ted and Mary begin dating, Pat and Norm team up to drive Ted away. Mary dumps Ted after she receives an anonymous letter revealing that Ted hired Pat to find her. Ted then angrily confronts Pat and Norm, who deny sending the letter, and Ted leaves in frustration. Dom, who is revealed to be Mary's ex-boyfriend "Woogie", later shows up in her apartment and admits to writing the letter. She previously had a
restraining order against Dom after he became obsessed with her, which started again when Ted found her despite being married with kids. Norm and Pat, listening outside, intervene and save Mary from Dom. Ted then arrives along with
Brett Favre, another ex-boyfriend of Mary's whom she dumped after Norm lied about him insulting Warren. Ted declares Brett should be with her since he is the only one not to use deception to win her over. After reuniting Brett with Mary and leaving the other men defeated, a heartbroken Ted leaves in tears. However, he is followed out by Mary, who has decided she'd be happiest with him, and they kiss. Magda's boyfriend uses a sniper rifle to attempt to shoot Ted for kissing Mary (as he is also infatuated with her) but hits one of the nearby band members who had been narrating their love story instead. ==Cast==