A pair of comic book painters named Holden McNeil (Ben Affleck) and Banky Edwards (Jason Lee), who live in New Jersey, have been best friends since 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 (Joey Lauren Adams) 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.