Lenny (Tom Sizemore) is the kind of man who simply cannot get through the day without messing up, or suffering some amazing piece of bad luck. As a consequence, he has lost every one of the jobs his uncle has set him up with. That's how he loses his job as a gas station attendant: he leaves the place to ferry Eloise, a particularly good-looking girl, to a job interview. She looks like a good thing for him though, and they move in together, despite a lack of funds. Soon, he even loses his job at a porno flick, when that gets raided by the police. Oddly, he is almost insanely jealous of Eloise's former boyfriends. After the pair of them become homeless, he cooks up a scheme to recoup some money that proves he is completely clueless, once and for all.