In 1985, gawky teenager Ted goes to pick up his beautiful, charming prom date, Mary, at her home. He nervously asks to use the bathroom and, after urinating, accidentally zips his pants over his scrotum. With part of his genitalia stuck in the zipper, an agonized Ted seeks help from Mary’s parents, who call the paramedics. Ted is rushed to the hospital, thereby missing his chance to win Mary’s heart. Years later, twenty-nine-year-old Ted is still single and obsessed with the long-lost Mary. Prompted by his best friend, Dom, Ted hires Healy, a shifty private detective, to search for her. Healy locates Mary in Miami, Florida, where she works as an orthopedic surgeon. While observing her from afar, Healy becomes infatuated with her. He lies to Ted that Mary has gained weight and has had several children by different fathers. By deceitful means, Healy briefly succeeds in dating Mary, before her close friend, a disabled architect named Tucker, reveals him to be a liar. Healy follows Tucker, and discovers he is actually Norm Phipps, a pizza delivery man posing as a disabled architect in the hope that Mary will fall in love with him. Back in Rhode Island, Ted decides to reunite with Mary regardless of Healy’s negative report. On the drive down, he gives a ride to a serial murderer, thinking he is an innocent hitchhiker. While stopped at a rest stop, the killer leaves the body of his latest victim in Ted’s car. Upon discovering the body, police arrest Ted for the murder. Dom arrives to bail him out, and the police apprehend the actual murderer. Arriving in Miami, Ted finally gets his chance to woo Mary. Their relationship develops in a promising way until Mary receives an anonymous letter that exposes Ted’s link to Healy. She breaks up with him, and is soon pursued by Dom, who, unbeknownst to Ted, happens to be Mary’s ex-boyfriend, “Woogie.” Mary, who previously got a restraining order against Dom, rejects his advances. They are joined by Ted, Norm (a.k.a. “Tucker”), and Healy. With all of them in a room together, it becomes apparent to Ted that Mary’s only upstanding boyfriend was National Football League (NFL) player Brett Favre, and that her and Brett’s relationship was unfairly sabotaged by Norm. Ted selflessly brings Mary and Brett back together. However, as he is about to leave Miami, Mary chooses Ted over Brett.