Kevin Smith is a loser. He has also never in his life, on any level, been cool. Worst of all, he is an uncool loser who lacks self-awareness. And while Chasing Amy is easily his best film, with a number of qualities to recommend it, it is severely hamstrung by the fact that it is written and directed by an uncool loser trying to write cool winners.
To Smith's credit, when he made the picture, he was still very far from the pathetic creature he is today. A multi-millionaire whining and bitching about other actors and comedians hurting his feelings while desperately licking Marvel's ass in the hopes they will throw him table scraps in the form of an online-only pilot.
Back then, Smith was young, had some edge, and likely hung out with people who WERE cool and/or winners. Thus, to some extent, he could approximate their mannerisms, behavior, and speech.
And yet, everything is at least slightly off. The way Affleck's Holden, a wildly successful comic book writer who is witty and attractive with women behaves is oftentimes too lame, other times too exaggerated, and other times too whiny and childish. Adams' Alyssa often speaks in a manner no hip, attractive 90's lesbian ever would and becomes angry and combative in a way at odds with her character's usually calm, easy-going demeanor. It's a consistently shaky representation of reality.
Normally, it's not so bad. There is enough verisimilitude that you can still appreciate the jokes and banter, which is done better than in most such movies and has genuine funny moments and well-timed twists. Affleck is believable in his role and sells even the weaker dialogue energetically and earnestly.
The problem comes with the movie's big romantic moments. Holden's confession to Alyssa in the car is very genuine and heartfelt. So too is him giving her his comic at the end. They would have been appropriate and touching...if Holden was an uncool loser. But he's not. He's a cool winner.
Someone like oh, say...a Kevin Smith laying his heart bare and professing his undyling love and admiration for Alyssa in the car would make perfect sense. Hell, those words are ones he wish he could say, or would try to memorize. But a Holden would never prostrate himself like that.
Similarly, Holden would never make a grand romantic gesture at a public event, or write a comic that is such a literal representation of what he experienced. It's the behavior of a completely different character.
Also, the less said of the threesome idea, the better. I don't know how someone didn't talk Smith out of such hare-brained stupidity, that its assumptions about Banky are as ridiculous as anything he said about gays, and that Holden's proposal would only make sense if the movie had established he was recently released from the loony bin after a lobotomy. Even if he had no clue how to progress the plot to its next point, there is no excuse for such immersion-shattering idiocy.
Perhaps even worse, Kevin Smith's identity becomes a problem with the movie's central message.
As much as promiscuous women who want to settle down as they age wish all people would believe otherwise, one's past does matter. It does speak to a person's character. And with women, how many men they have been with, or what they've done with them profoundly affects who they are.
I've been with women who had similar pasts to Alyssa. In real life, they're not fun, vibrant, and witty. They're dull and listless, with dead eyes and no reaction to the type of jokes and banter Holden was throwing out.
You know who puts a woman on a pedestal, blithely ignores her past, and even proclaims this to be a virtue? A loser...like Kevin Smith.
It's hard to know how to rate Chasing Amy. It's an amusing if frequently false plot with sincere emotional moments that also make no sense for the characters capped off with a terrible message.
All because Kevin Smith didn't acknowledge the limitations of his own identity.
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