A pair of comic book authors named Holden McNeil and Banky Edwards, who live in New Jersey, have been best friends for 20 years. They spend their time working in their studio, and in the evenings they are going out. But their friendship is about to be disputed for the first time in their life, when a beautiful young lesbian woman named Alyssa Jones enters their life and Holden falls in love with her. Now Holden has to deal with Banky's jealousy, and with his new girlfriend's very rich past.
—rsilberman
Holden and Banky are two average guys who just need someone to bring out their hidden secrets. Enter Alyssa Jones and Hooper LaMont, two homosexuals who are slightly more experienced than the former two. Together, Hooper and Alyssa show Holden and Banky that being gay isn't as bad as they might think. Meanwhile, Holden develops an 'untainted' love for Alyssa, one which she finally sees in him as well, taking Holden on a journey through the complexities of love in the 90s.
—Simon Friend
Holden and Banky are best friends and authors of a popular comic book called "Bluntman and Chronic". Holden falls in love with Alyssa, also a comic book artist, who happens to be a lesbian. Holden's new relationship with Alyssa strains his life-long friendship with Banky, and soon the relationship between Holden and Alyssa hits a wall due to Holden not being able to deal with her past.
—Oliver Yun
Holden and Banky are comic book artists. Everything's going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.
—Kevin Gillease
SYNOPSIS
Holden McNeil (Ben Affleck) and Banky Edwards (Jason Lee) are comic book artists and lifelong friends. Holden is the calmer, more reasonable of the duo; Banky, meanwhile, is the caustic and short-tempered half. The story opens at a comic book convention in New York City where the two are promoting their latest comic series 'Bluntman and Chronic'. During a panel discussion, they meet Alyssa Jones (Joey Lauren Adams). She is a struggling comic book writer whom is friends with the African-American comic book writer and activist Hooper (Dwight Ewell) who puts on this militant image to hide his flamboyantly gay personality.
That evening, the four go out for drinks together at a local bar where Holden is attracted to Alyssa based on their conversation during a dart game. Through Hooper she invites Holden to a get together at a bar she frequents. Banks comes along and while there Alyssa is asked to sing a song. During the song Banky notices that they are in a female gay bar and that Alyssa is singing the love song to a woman in the audience and not to Holden who thinks the song is for him. The four of them end up at a booth and Alyssa and Banky have an involved conversation about sex with women and Holden is visibly upset about Alyssa being a lesbian. However, they have discovered they are both from the same area of New Jersey and the two begin hanging out, and a deep friendship develops. During their discussions it is clear that Holden has a very narrow heterosexual view on male female relationships and sex in general. The new friendship does not sit well with the homophobic Banky, who dislikes and distrusts Alyssa and is bothered by the relationship that develops between her and Holden. Holden and Banky's business relationship suffers as well -- the two had been on the verge of signing a lucrative deal to turn Bluntman and Chronic into television show and Banky feels that Holden is no longer taking their combined efforts or the TV show seriously.
Eventually, Holden is no longer able to contain his feelings, and confesses his love to Alyssa. She is initially angry with him and walks away.Holden follows her and they have a heated discussion about their relationship and she walks away again. Holden is confused and while returning to his vehicle Alyssa runs up, they embrace and that night the two begin a romantic relationship. Banky walks in the next morning and finds them together sleeping on his couch in the studio. This new development worsens the tension between Holden and Banky who distrusts Alyssa and that his friend is going to be hurt when the relationship fails. Banky runs across an old friend who grew up with Alyssa who tells him a sexual adventure story from Alyssa's past. Banky reports to Holden that Alyssa participated in a threesome with two guys during high school, which earned her the nickname "Finger Cuffs" for getting it from both ends. Holden is deeply disturbed by this revelation, having believed based on their conversations about love and sex that he is the first man Alyssa had ever slept with.
Holden asks advice from Hooper who tells him that if he wants his relationship with Alyssa to work, he must be honest and truthful as to put whatever is bothering him behind him by being up front with her about it and then put it behind him. Hooper also tells Holden he believes the issues with Banky is that Banky is jealous and in love with him and that his macho sexual banter is a disguise for his true feelings.
The following evening, Holden confronts Alyssa while attending a hockey game and he clumsily attempts baiting her into confessing in the stands. During a tearful argument in the parking lot, she tells Holden about her youthful sexual experimentations involving men. She apologizes for letting him believe that he was the only man she had been with but justified it by saying she could see that he took pleasure in the thought. However, she refuses to apologize for her past, and Holden leaves feeling angry and confused.
Later, during lunch at a local diner with the local stoners and drug dealers Jay and Silent Bob (Jason Mewes and Kevin Smith), who were the inspiration for the Bluntman and Chronic comic book characters, Holden gives them their monthly residual pay for sales of the comic book. Here he confides in them about his troubled feelings and relationship with Alyssa. Speaking more than one line for the first time, Silent Bob mentions chasing Amy and reveals that he was once in a relationship "a couple of years ago" which was similar to Holden's. Despite the fact that he was in love with his girlfriend, Amy, his insecurities about her adventurous sexual past caused him to sabotage the relationship and leave her. Angry at himself for letting her go, he has "spent every day since then chasing Amy".
Inspired by Silent Bob's story, Holden devises a plan to fix both his relationship with Alyssa and his fractured friendship with Banky. He invites them both over and tells Alyssa that he would like to get over her past and remain her boyfriend. He also tells Banky that he realizes that Banky is in love with him... kissing him passionately to prove the point. Holden suggests that the three of them should have sex with each other in a threesome so he will no longer be envious of Alyssa's broader experiences and it will resolve Banky's issues with them as a couple. Banky reluctantly agrees to participate. Alyssa is appalled and refuses, at which Banky expresses his relief. Alyssa tries to explain to Holden why his plan is so wrong. Before leaving, she states that she will always love him but her past is in the past and she will not be his whore and slaps him across his face. Banky then leaves without saying a word.
One year later, the story has Banky busy promoting his own new comic book at a convention in New York. It is revealed that Holden has dissolved their partnership over Bluntman and Chronic, leaving the viewer with the assumption that he sold the publishing and creative rights over to Banky (which is corroborated in the beginning of 'Jay and Silent Bob Strike Back'). Banky looks over and sees Holden at a distance, who silently congratulates him for his success on the new book. Banky gestures over to a booth hosted by Alyssa, and provides wordless encouragement with a hand gesture implying a coming together to Holden to go talk to her. Holden has a brief tender emotional conversation with Alyssa, and gives her a copy of 'Chasing Amy', his new comic based on their failed relationship. Holden asks her to contact him. After Holden leaves, Alyssa's girlfriend (Virginia Smith) comes back to the booth and asks who that was. Alyssa feigns indifference,casually tosses his comic on the floor behind her and replies, "Oh, just some guy I knew." She then turns to sign the next fan's material.