"It's not who you love. It's how."

1997 film on love and sexuality, written and directed by Kevin Smith.

"Clerks had been over-praised, Mallrats had been over-bashed. We'd been to both ends of the spectrum. The third time is always supposed to be the charm, so we were able to approach Chasing Amy from a very liberated position: What better could they ever say about us than they did the first time, and what worse could they ever say about us than they did the second time? And that made it somewhat easy to make an honest film."
Kevin Smith - www.viewaskew.com

background

Released as the third part of the New Jersey Trilogy, Chasing Amy was a return to the subject of bittersweet relationships after the critically misunderstood and comparatively comic book-like Mallrats. Made within a respectably frugal budget of just $250,000, the film surpassed the acclaim received by his debut Clerks, earning a place on many a critic's top ten lists for 1997 and even going so far as to be rated by Quentin Tarantino as the best film of that year.

Despite being shrugged off by some as being a 'mere' chick-flick, Amy went far beyond the standard boy meets girl traumas and observations presented in Clerks. Loosely based on his relationship with Joey Lauren Adams it was, as Kevin put it, his own life laid out on a slab for the world to see. While he's quick to point out that Joey was never a lesbian, his relationship was nevertheless hindered by the feeling of having to measure up to a partner who had lived more life than he had.

"I was a guy from Highlands, New Jersey, content to live and die in the same twenty mile radius I'd spent almost all of my life in to that point. She was from North Little Rock, Arkansas, but you wouldn't know it. Joey had done some travelling, living in Australia, Bali, New Orleans, San Diego, and then settling in Los Angeles. I like my gatherings small and intimate; Joey likes hers huge, loud, and loaded with spirits of many kinds. But these were nothing compared to the differences in our sexual history."
Kevin Smith - www.viewaskew.com

Although it only picked up a handful of independent awards and nominations, mainly for Joey Lauren Adams as best actress, I think it's still Kevin Smith's best work to date. The comedy moments will make you laugh as much as any of his other films but it's the first one so far to bring with it an equal portion of tears. If you're given to blubbing uncontrollably at films, you're advised to keep a good stock of hankies beside you while you watch it.

Alyssa
Looks like a very personal story.

Holden
I finally had something personal to say.

synopsis

The film opens with life-long best friends Holden McNeil (Ben Affleck) and Banky Edwards (Jason Lee), the sole producers of Bluntman and Chronic, a successful comic book heavily based on the characters of Jay and Silent Bob. The new issue is selling like crazy, there's interest from television networks concerning a possible animated series and life is sweet until they are introduced to Alyssa Jones (Joey Lauren Adams) at a convention. Alyssa is also a comic artist, albeit a less successful one. Idiosyncratic Routine doesn't pander to the adolescent male fantasies of most comic books and, as a result, appeals to only a very selective audience.

Alyssa
Nope. I’m happy my stuff gets read at all. There’s very little market for hearts and flowers in this spandex-clad, big pecs, big tits, big guns field. If I sell two issues, I feel like John Grisham.

Holden is helplessly smitten with Alyssa and is convinced that she feels the same way about him until he discovers that her affections belong to another woman. As their friendship deepens and slowly evolves into love, Banky begins to see Alyssa as a threat to his friendship with Holden and the comic, and takes it upon himself to stop their relationship by any means possible. When he discovers some sordid details about Alyssa's past sexual exploits with two guys at school, it bursts Holden's fantasy bubble that he's been the only man in her life up to that point and it freaks him out, knowing that it shouldn't bother him but being eaten up about the fact that it does. When he confronts her about it, it puts a strain on their relationship that, misguidedly, Holden sees as having only one unlikely solution...

dvd profile

Available as part of the much-mooted Criterion Collection, the disc features the film itself, obviously (duration: 1h 53m), and a wealth of extra features including:

sources:
(the quotes) http://www.viewaskew.com/chasingamy/howwhy1.html
(nailing down the specifics) www.imdb.com
and the fact that i've seen it about a million times.