Chasing Amy

Chasing Amy is a 1997 American romantic comedy film written and directed by Kevin Smith. The central tension revolves around sexuality, sexual history, and evolving friendships. It is the third film in Smiths View Askewniverse series.

Holden McNeil Ben Affleck and Banky Edwards Jason Lee are comic book artists and lifelong friends. Holden is the friendly, more mildmannered half of the duo Banky, meanwhile, is the loud and fiery half. Everything is going well for them until they meet fellow comic book artist Alyssa Jones Joey Lauren Adams at a comic book convention in New York where they are promoting their comic Bluntman and Chronic. Holden is attracted to Alyssa, but soon learns that she is attracted to women. The two begin hanging out, and a deep friendship develops. Eventually, Holden is no longer able to contain his feelings, and confesses his love to Alyssa. She is initially angry with him, but that night, the two begin a romantic relationship.This new development worsens the tension between Holden and Banky, who hates and mistrusts Alyssa and is disturbed by her and Holdens relationship. Banky investigates and uncovers dirt on Alyssas past, and he reports to Holden that Alyssa participated in a threesome with two guys during high school, which gave her the nickname Finger Cuffs. Holden is deeply upset by this revelation, having previously believed that he is the first man Alyssa had ever slept with. He angrily confronts Alyssa while attending a hockey game, and clumsily attempts baiting her into confessing. During a tearful argument, she tells Holden about her many youthful sexual experimentations. She apologizes for letting him believe that he was the only man she had been with. However, she refuses to apologize for her past, and Holden leaves feeling disillusioned and furious. ........

Source: Wikipedia