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So needless to say, I could feel Holden’s pain. And using this personal point of reference, I almost forgot that I was watching a Kevin Smith movie. I was able to ignore the artless dialogue and synthetic personalities and get absorbed into this flick the way I never could with Clerks. But it isn’t just me. The movie really does begin to change tone as Holden overcomes his initial disappointment and starts to honestly pursue a friendship with Alyssa. They have a lot in common and they bond in a very real way. They have frank, ardent discussions about sexuality that sound a bit naive today, and will sound downright vulgar if you’re not accustomed to sexually charged dialogue. But at the time, it wasn’t particularly common to see such an open and (surprisingly) earnest consideration of homosexuality on screen. Suddenly, Chasing Amy turns from a dimwitted, self conscious farce into an unexpectedly compelling romance.

But despite the occasionally weighty material, the movie remains accessible. This is still a romantic comedy and in a sense, it really isn’t so different from any other in that person A is in love with person B, but there is an obstacle keeping them apart. Halfway through the movie the obstacle is (seemingly) overcome, but with unpredictable consequences. Longing for something you can’t have is painful, but it isn’t nearly as complicated as making reality fit what you imagined. Some of the usual rom-com tropes are present here – there’s a sappy “falling in love” musical montage about forty minutes in and there’s even a Gay Best Friend, although this one is a rather refreshing spin on a very tired cliché. But it’s the third act of the film that really shines. None of the characters are ever fully formed but they grow on you, and you really do come to care what happens to them. Holden is a semi conservative Catholic boy who expects unrealistic things from romantic love. Alyssa is a free spirit who’s been places and done things Holden can’t even imagine. The two leads are obviously star crossed from the beginning and to its credit the film resists the urge to end on a treachly, predictable note. They way the story ends seems both inevitable and real.

Chasing Amy never completely stops being what it is, and of course that is a Kevin Smith movie. It is insecure, neurotic and desperately in need of your validation. It’s funny but not as funny as it thinks it is. It’s likeable and engaging, but only after an initial period of awkward fumbling. Like its creator, this movie is to some degree a nerd over exerting himself and largely becoming a bigger nerd in the process. But more than any of Smith’s films before it, this one has something to say, and more than any since, it succeeds. There’s a sincere earnestness to it that quickly outgrows its pedestrian roots and that clodhopping first act. This is the first Kevin Smith film that didn’t leave me skulking from the theater ashamed to be a member of the Slacker Generation. Unlike most rom-coms Chasing Amy ends with a poignant and realistic vibe. It’s not quite a warm embrace; it’s more like a well meaning pat on the back. So maybe it’s a bit of a stretch to call out every Kevin Smith character as Kevin Smith. Maybe it’s more accurate to say that Chasing Amy is an open window into the soul of its creator and for one brief shining moment in the spring of 1997, it was a great view.

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