A romantic comedy written and directed by Kevin Smith, Chasing Amy stars Ben Affleck and Jason Lee as friends and comic book creators Holden McNeil and Banky Edwards, whose lives are turned upside down by a girl, Alyssa Jones, played by Joey Lauren Adams. After Holden and Amy meet, the pair become friends, although the lesbian Alyssa wants things between them to remain platonic. Holden falls for her, however, and complicates things when his confession causes reluctant Alyssa to begin a romance with him in spite of her professed sexuality. His best friend Banky is angry at the budding relationship, as he is suspicious of Alyssa and fearing the loss of his friend.
Determined to break the new couple up, Banky finds out something surprising about Alyssa's relationship history, that Holden was not the first man she'd ever been with as he believes. After Banky shares the news with Holden he argues with Alyssa about it, and although she is sorry for misleading him, she will not show remorse for who she is and what she did before she ever met him. Holden later has a talk with a friend who had been in the same situation with a woman but, rather try to save their relationship, he drove her away and has regretted it since. The story compels Holden to try to make amends both with Alyssa and Banky.
Holden's grand scheme is to have a physically intimate night with both of them at once, as he realizes that his friend is secretly in love with him. The suggestion of the idea causes both the woman he loves and his best friend to leave him. Holden uses the experiences to write a comic book about the relationship with Alyssa, which he presents to her a year later at a convention at the prompting of Banky who seems to be on the road towards forgiving him. The gesture towards Alyssa allows Holden to move on with his life.