Chasing Amy (1997)

Best friends Holden McNeil and Banky Edwards are enjoying success as the creators of the cult comic book 'Bluntman and Chronic.' When they meet fellow comic book artist Alyssa Jones, Holden's desire for the beautiful charmer is immediate. Alyssa, however, has set her romantic sights elsewhere but decides, nevertheless, to pursue a friendship with Holden. This presents Holden with a dilemma: feeling the way he does, can he merely be friends with this woman? Banky, who knows Holden best, doesn't think so. As the friendship deepens, so do Holden's affections for Alyssa. And cautiously, yet effortlessly, so do Alyssa's for him. With their relationship strugging to define itself, Banky grows more and more frustrated at the notion of losing his best friend to emotional adulthood.