Chasing Amy (1997)
http://www.imdb.com/title/tt0118842/
Holden and Banky are best friends and authors of a popular comic book called "Bluntman and Chronic" (based on Jay and Silent Bob of "Clerks" and "Mallrats" fame). Holden falls in love with Alyssa, also a comic book artist, who happens to be a lesbian. Holden's new relationship with Alyssa strains his life-long friendship with Banky, and soon the relationship between Holden and Alyssa hits a wall due to Holden not being able to deal with her past.
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