Larry Gigli (Ben Affleck) is a small-time enforcer for a small-time hood named Louis. Larry's latest assignment is to kidnap a retarded young man named Brian (Justin Bartha) to help Louis and his colleagues can apply some pressure to Brian's brother. So Larry picks up Brian and brings him back to his apartment. A beautiful woman (Jennifer Lopez) who says her name is Ricki tells Larry that she has also been hired by Louis to make sure he does not mess up the job. Larry's macho ego is affronted, but he is attracted to Ricki, even after she tells him she is gay. A lot of bickering and bantering later, much of it involving mind-numbing debates over who is the boss and straight vs. gay sex, plus encounters with the mother of one and the ex-lover of the other, Larry and Ricki have to decide whether they are willing to hurt or kill Brian and that leads them to think differently about themselves and each other.