Peter Parker and Mary Jane Watson
Mary Jane is Peter Parker (Tobey Maguire)'s childhood and high school crush and only sweetheart. At the time, she is dating the high school bully, Flash Thompson (Joe Manganiello), but breaks up with him at their high school graduation ceremony. Desperate to escape her abusive, alcoholic father, Mary Jane begins to pursue a career in acting, but she secretly waitresses at a diner after being rejected at an audition. Peter's friend, Harry Osborn (James Franco), is her first boyfriend after leaving high school, but she becomes attracted to Peter's alter-ego, Spider-Man, after the superhero saves her from the Green Goblin. She later shares a passionate kiss with Spider-Man while he is suspended upside down after he saves her from a gang of thugs. Mary Jane begins to grow more distant from Harry, denying his advances. Her feelings for Peter grow when he tells her what he supposedly told Spider-Man about her. After Harry sees Peter and Mary Jane holding hands, he gets angry and breaks up with her.
Harry's father Norman Osborn (Willem Dafoe) knows of Spider-Man's secret identity and finds out about his feelings for Mary Jane from his son. As his criminal alter-ego, the Green Goblin he kidnaps her and holds her over the Queensboro Bridge, telling Spider-Man that he must choose between her and a group of children caught in the Roosevelt Island tram car. Spider-Man saves both Mary Jane and the children, however. At the end of the film, Mary Jane tells Peter that she loves him and they kiss. However, Peter shies away from her as he is afraid for her safety, and thus does not want to get involved with her. She is heartbroken by his rejection, but realizes that her kiss with Peter reminded her of the one she shared with Spider-Man and suspects that he is the superhero.