Holden and Banky are comic artists and great friends. While Holden is level-headed and Banky is impulsive, the two have worked well together until a convention in New York. There, while promoting "Bluntman and Chronic," Holden meets fellow artist Alyssa. Over the time that the two spend hanging out, Holden's feelings grow. Things become complicated when he discovers that Alyssa is a lesbian; although they still spend time together, Holden's feelings only grow and he eventually tells her. While furious, she agrees to try heterosexual dating.
This shift agitates the bond between Holden and Banky, causing Banky to research Alyssa's history and finding lots of sexual dirt on her. This news shakes Holden's perception that he was Alyssa's first guy, and he confronts her about it. Alyssa apologizes for given Holden that impression, but doesn't apologize for her past.
The film then jumps ahead by one year where Holden has sold his rights to "Bluntman and Chronic" to Banky. While at another convention in New York, Banky sees Holden from afar and both congratulates him motions over to a booth being run by Alyssa. Alyssa and Holden have a brief conversation where he gives Alyssa a copy of his new book, "Chasing Amy," a comic about their relationship and all its problems.