I think this might have been the first Kevin Smith movie I ever watched. This or “Clerks”, I do remember watching them in the same month. That could explain why I might be switching the viewing order. Either way, this movie is notable among Kevin Smith’s filmography for a couple of reasons. First, it takes a more dramatic approach to it’s story telling. Yes there is obviously humor. But it follows the relationships of the characters on a more serious level than most of Smith’s other movies. The second reason, the story of a straight white man trying to date a gay woman definitely makes this one of the more potentially awkward movies to watch in the modern era.

Yes, that’s the general plot of the story. It focuses on Holden (Ben Affleck) who is a comic book artist along with his best friend Banky (Jason Lee) and Holden is attracted to another comic book artist they meet named Alyssa (Joey Adams). But Alyssa is gay so they at first just become good friends. But Banky becomes resentful that Alyssa is seemingly coming in between him and Holden. And somehow, Alyssa decides she does want to enter a romantic relationship with Holden. But that intensifies the drama and the conflict starts to mess everything up.

It’s very easy to just read a plot summary of this movie online and assume it hasn’t aged well. Criticize it for having a “heterosexual narrative”. And to be fair, there was a brief bit on the show “How I Met Your Mother” where Barney tries to pick up a lesbian. So I totally see and understand where these criticisms are coming from. And the 1990s in general weren’t exactly the most insightful when it came to exploring LGBTQIA+ themes and characters. But I will argue that if you actually watch the film instead of reading about it, you do see that things probably play out different from what you are expecting.

Holden & Alyssa do take the time to actually build a friendship and get to know each other on an intellectual and emotional level. Once that groundwork has been established, you do get the idea that Alyssa isn’t exactly firm in identifying as simply gay. It can be argued that she is one of the first modern examples of a gender fluid character. You might even argue that she is more pansexual than just homosexual. Might have been an awkward line to write but I’m sticking with it. The catalyst that intensifies the conflict in the movie is the revelation that she once participated in a threesome with two guys. The evidence is there that Alyssa is more open about her sexuality, which is said to be generally true about women in the real world as well.

While the plot does revolve around what can be seen as a straight man’s fantasy, by the time you reach the end of the movie it becomes clear what the movie is trying to talk about. It’s about coming figuring out who you are and what you want out of life and relationships. Of coming to terms with your past and your partner’s and working together to find happiness. The title of this movie comes from a story shared by Silent Bob. Yes, the stoned dynamic duo of Kevin Smith’s cinematic universe return in this movie. He tells Holden how he used to have a similar relationship with a girl he refers to as Amy. But it ended when he couldn’t handle her promiscuity and later regretted breaking up with her. This is mirrored later on when Holden gathers Alyssa and Banky and offers that they all participate in a threesome.

From Holden’s perspective, Alyssa has an open approach to sex so he thinks she’ll say yes. And it’s clear to him that Banky is a closeted gay man, despite the various homophobic remarks he’s made in the film. But it’s important to note here that Alyssa easily refuses and ends the relationship with Holden. Just because she has had this experience in the past and she is the most sexually liberated person in the group, that doesn’t mean that’s all she wants. She’s a person that has emotional wants and needs, someone that should be given more thought and respect than what Holden’s offer implies. It’s ultimately Holden’s selfishness and lack of emotional connection with Alyssa that ends their time together. And it’s also what ties those themes of self-understanding and romantic equality together.

Look, I understand why this movie not be for everyone. There are still some scenes that do handle this subject matter a little clumsily. And it still has that 1990s feel and approach that could rub people the wrong way – pun unintended. But I do think this movie is about deeper emotional & sexual/romantic issues that are highlighted due to the lack of an expected happy ending – also unintended. Give it a watch and see if you can make that same deeper connection that we all aspire to find with our partners in the real world.