Chasing Amy shows the price of insecurity. Holden, a successful comic book artist, feels insecure dating Allisa, who is a free spirited bi-sexual woman that knows exactly who she is and did the painful work to get there. The relationship is set in motion by a comic book creator named Hooper, who leans deep into the “Black Rage” angle in front of the panels at comic book conventions but is flamboyantly gay off stage. Holden and his comic book partner Banky devise a bit to where Holden in character self-destructs on stage. Banky is in the crowd provoking him, and then Hooper fires a prop gun at Banky and screams “Black Rage! I’ll kill all you!” Which clears out the crowd, leaving only Holden, Banky, Hooper, and Allysa.
They all go out for a drink, and Banky spends the evening denying Archie and Jughead were lovers, which foreshadows his coming out as gay. But his insecurity revolves around a repressed homosexuality, because in the 1990’s being gay was still seen as being less masculine. So, Banky over-compensates and says disparaging remarks about gay people throughout the whole movie.
This beer sets up the much bigger insecurity. Holden and Allysa have a nice night, and the next time they all go out Holden is smitten. At the bar Allysa sings onstage and then makes out with a woman, then Holden realizes she is not straight. He’s a sheltered guy and has lived a conservative life. So, he does not know how to react, and leaves awkwardly. Later, she knocks on his door and says, “You don’t fall into a stereotype. We’re going to be friends.”
After that, they fall into a platonic relationship, where they go on several dates without any of that annoying sex. As they grow closer, Banky gets more jealous of Allysa. This erupts in a confrontation where Banky is seeing her as a threat to his relationship with Holden. Banky tells holden that there will come a time when he’ll have to choose, and asks “what is this power she has over you?”
He tells Banky “Because I’m in love with her!”
Holden confesses this to her in the next scene. He tells her this passionate speech about how much he loves her that ends with “there is not another soul on this planet that has made me half the man I am with you.” Then she runs out of a parked car in the rain and starts yelling at him, telling him, “I am fucking gay! You assume I can turn that around because you got a fucking crush?” and then she tells him to go home. Then she runs after him and starts kissing him, because in the background of all of the men’s fear of confronting who they really are, she has been falling in love with him and not wanting to admit it to herself. Because she invested so much of her personality in identifying as gay, but to be bi-sexual means something vastly different.
Later, Holden asks Allysa, “why me?”
She tells him, “To not limit the likelihood of finding that one person who complimented me so completely. I was thorough looking for you. I got here on my own terms.”
Then Holden, with everything he ever wanted in the world, learns of her promiscuous past, and can't handle it. So, he shames her for her sexuality, and dumps her in the parking lot of a hockey rink.
Then Jay and Silent Bob show up, and Bob informs Holden he is “Chasing Amy.” He met a girl named Amy before, and she had an ex-boyfriend that she had threesomes with. Like Holden, Silent Bob broke up with Amy over his insecurities. Bob felt he would never measure up, be sexually adventurous enough, to satisfy her. He pushed her away and realized his mistake too late. “So now I spend every day Chasing Amy.”
Holden wants to fix it. But he is also 25 and remarkably inexperienced. Holden’s solution to feeling sexually inadequate is to suggest he, Allysa, and Banky all have sex together. Banky is on board, because he’s been wanting this his whole life, it’ll help him self-actualize. Allysa has been down this road and sees just how messy sex can make things. How it won't fix it. She is with him because she wants a stable monogamous relationship. She wants a good person to love, and to love her for who she is. To cherish her entirely, and not just use her for satisfying his own sexual insecurity. Holden is so wrapped up in his insectaries that he doesn’t see how disrespectful this is to her, and after she breaks up with him, she smacks him and says, “I won't be your fucking whore.”
One year later, there’s a comic book con. The wordless reuniting across the con floor of Holden and Banky is full of gentle smiles. Banky lets Holden know Allysa is at a panel nearby. Then at the end, when Holden shows her the book he wrote called, “Chasing Amy.” She smiles at him and is so proud of his growth, and they say goodbye again. He walks off alone, having become a better man. He had to lose everything to know what was important. His insecurities cost him the love of a good woman and his best friend. Now he spends his life Chasing Amy.