Chasing Amy (1997)

Chasing Amy is not your typical romantic comedy, as it’s directed by Kevin Smith, known for more cursing than you find in most rom-coms.  It stars a young Ben Affleck, who falls for a fellow comic book artist, played by Joey Lauren Adams, who turns out to be lesbian.

Throughout the film, he pursues every avenue to garner her affection and eventually they start a relationship. While Chasing Amy was applauded for its LGBTQ characters, putting it way ahead of its time, modern audiences would probably push back against a plot of a character pushing his love interest into going against her sexual orientation.