While promoting their comic
Bluntman and Chronic at a
comic book convention in the
Manhattan borough of
New York City, comic book artists and lifelong best friends Holden McNeil and Banky Edwards meet Alyssa Jones. A struggling writer working on her own comic
Idiosyncratic Routine, Alyssa is friends with Hooper, an African-American activist writer who militantly masks his flamboyantly gay personality to promote his comic
White-Hating Coon. Immediately attracted to her, Holden soon discovers her lesbianism while at an East Village bar called the Meow Mix. Holden and Alyssa soon bond, as they grew up in the same area of New Jersey, with Holden and Banky being natives of
Highlands and Alyssa being a native of
Middletown. This upsets the homophobic Banky, who resents Alyssa for intervening in their affairs. The duo's business partnership also suffers, as they had almost signed a lucrative deal to adapt
Bluntman and Chronic into an animated television series, and Banky feels that Holden has abandoned their project. Unable to conceal his feelings any longer, Holden eventually confesses his love to Alyssa. She is initially angry and upset with him, but they later reconcile and begin a romantic relationship that night, which worsens things with Banky when he encounters them sleeping on his couch in the duo's shared studio Bank-Hold-Up in
Red Bank the next morning. Banky encounters an old friend of his, who grew up with Alyssa and tells him she participated in a
ménage à trois with two boys back in high school, which earned her the nickname "Finger Cuffs". Banky relays the story to Holden, who becomes deeply disturbed by the revelation, having believed that he is the first man Alyssa had ever slept with. Believing that Banky is jealously in love with Holden, disguising his true feelings with macho sexual banter, Hooper advises Holden to be honest and truthful and ask Alyssa about her past. The following night at a hockey game, Holden confronts her and clumsily attempts to bait her into confessing, which she eventually does, and she storms out of the arena. In the parking lot, she angrily confirms the
threesome but defends her past sexual experiences, wanting to continue their relationship. Holden leaves feeling unsure. Later, Holden meets
Jay and Silent Bob, the inspirations for the characters Bluntman and Chronic, for lunch at a local diner. He hands them their monthly residual pay for book sales and discusses his troubles regarding Alyssa. The normally-mute Bob reveals that a couple of years earlier, he had a girlfriend named Amy in a relationship mirroring Holden's. Although he loved her, his insecurities about her past promiscuity caused him to break up with her. He regretted it and has since spent a long time "chasing Amy". Inspired by Bob's story, Holden devises a plan to fix both his relationship with Alyssa and his fractured friendship with Banky. He invites them over and tells Alyssa that he would like to get over her past and remain her boyfriend while telling Banky that he realizes that he is in love with Holden, kissing him passionately to prove it. He proposes a threesome, which he believes will both end his envy towards Alyssa's broader experiences and resolve Banky's issues with them being a couple. The initially shocked Banky agrees to participate, but is relieved when an appalled Alyssa declines, reasoning that the offensive proposal will not salvage their relationship. Alyssa and Banky both silently depart. One year later, at a convention, Banky, while promoting his own comic
Baby Dave, reveals to a fan that he now owns the publishing and creative rights to
Bluntman and Chronic, having dissolved his partnership with Holden. Holden silently congratulates Banky on the success of
Baby Dave, and Banky gestures him over to a booth hosted by Alyssa, encouraging him to speak to her. During their brief emotional conversation, Holden gives her a copy of
Chasing Amy, his new comic based on their failed relationship, and asks her to contact him if she has anything to say about it. After he departs, Alyssa's new girlfriend arrives and asks about him. Smiling and teary-eyed, Alyssa feigns indifference, casually moves his comic aside, and dismissively replies, "Oh, just some guy I knew." ==Cast==