Holden McNeil, portrayed by Ben Affleck, and his best friend Banky Edwards, played by Jason Lee, are two comic book artists navigating the complexities of creativity and friendship. At the outset, they find themselves at a comic book convention in New York City, enthusiastically promoting their latest venture, the comic series Bluntman and Chronic. While attending a panel discussion, they encounter Alyssa Jones, portrayed by Joey Lauren Adams, a passionate comic book writer with a vibrant personality. Her friendship with the outspoken activist Hooper adds depth to their gathering that night when the four of them go out for drinks.

As fate would have it, Holden feels an unexpected attraction to Alyssa, kindled during a lighthearted game of darts. When she invites him to a bar she frequents, Banky tags along, unaware of the evening’s revelations. Here, in a twist of circumstances linked to Alyssa’s identity, it becomes evident to Banky that she is singing a love song to a woman, not to Holden, who mistakenly believes the affection is directed at him. This revelation creates tension as Banky grapples with his unease over Alyssa’s sexuality and his protective instincts toward Holden.

Despite this, Holden and Alyssa discover shared roots in New Jersey. Their connection blooms into a profound friendship, but it is marred by Holden’s rigid views on relationships, clashing with Banky’s growing mistrust of Alyssa’s influence over their partnership. As Holden’s feelings for Alyssa surge, he bravely admits his love to her. Initially taken aback and furious, she walks away only for them to later embrace and ignite a romantic relationship that complicates the dynamics between the three friends.

The following morning, Banky finds them together, straining their friendship further. Banky’s discomfort escalates when he learns about Alyssa’s controversial past from an old acquaintance, who shares an eye-opening story that unsettles Holden, challenging his perception of their relationship. Seeking guidance from Hooper, Holden realizes he’s been living in ignorance and must confront Alyssa about her past if their relationship is to survive.

Their ensuing confrontation at a hockey game spirals into a heated exchange where Alyssa reveals her sexual history, leading to confusion and anger for Holden as he struggles with feelings of inadequacy. Through a lunch discussion with the eccentric Jay and Silent Bob, he reflects on his predicament as Silent Bob shares his own past romantic failures, igniting an idea in Holden that proposes a unorthodox solution to mend their fraying bonds.

In an unexpected twist, Holden suggests a threesome to reconcile the emotional hurdles among them, aiming to alleviate understandings about Alyssa’s past and Banky’s jealousy. Alyssa, shocked and appalled, firmly rejects this proposal, emphasizing her individuality and past experiences while maintaining her love for Holden. Resolute in her stance, she walks away, leaving Banky and Holden at an impasse.

Fast forward a year, the comic convention finds Banky finding his own footing, promoting a new comic title, while Holden has dissolved their partnership over Bluntman and Chronic. Observing from a distance, Holden gives a silent nod to Banky, signifying respect for his friend’s achievements. The reunion between Holden and Alyssa, though brief, contains an undercurrent of nostalgia, culminating in him gifting her a copy of Chasing Amy, a comic reflecting on their tumultuous relationship. As they part ways, Alyssa shares a guarded comment with her girlfriend, leaving the impressions of their bond swirling in ambiguity and lingering memories.

“Oh, just some guy I knew.”