It's the city that never sleeps and Alfie Elkins (JUDE LAW) is a limo driver who's just as prone to driving his rich clients, such as Dorie (JANE KRAKOWSKI), to their destinations as he is to have sex with them in the back of the limo. Although he and his best friend Marlon (OMAR EPPS) hope to buy the limo business from their boss, Mr. Wing (GEDDE WATANABE0), his real interest is in bedding as many women as possible, all while avoiding any sort of commitment.
That said, he has a quasi, semi-regular girlfriend in the form of single mom Julie (MARISA TOMEI), but that ends when she tires of his mindset and shenanigans. After a one-night stand with Marlon's on-again, off-again girlfriend, Lonette (NIA LONG), Alfie moves on to wild-child Nikki (SIENNA MILLER) who turns out to be a manic depressive and then Liz (SUSAN SARANDON), a rich and sophisticated older woman who briefly takes him as her lover.
As Alfie constantly informs us of how he feels about them, himself and life in Manhattan, he eventually begins to see the error of his romantic ways and hopes to set things straight before it's too late.