The bulk of Friends with Money takes place between two dinner scenes, in which four mostly well-to-do women gather for food and conversation with each other and the men in their lives, and then spend the drive home gossiping about each other with their partners. As you go home from this movie, you may find yourself itching to join in; the characters have an engaging, if not always appealing, familiarity—and the situations in which they find themselves are so amusing, if occasionally aggravating—that you may have an opinion or two of your own on the state of their lives and what they ought to do with themselves.
It's something of an inside joke that the one friend in this movie who isn't flush with money is played by Jennifer Aniston, the former million-dollars-an-episode Friends co-star. She plays Olivia, a former high school teacher who quit her job when the children began giving her quarters; she now works as a maid and fills her time smoking pot, "borrowing" face cream and vibrators from her clients, collecting free samples of cosmetics from department stores, and phone-stalking a married man with whom she once had a brief affair.
Olivia's friends, all of whom are pretty wealthy, worry about her, but they're not sure how to help. Should they give her some money, to bring her up to their level? No, that would be awkward. Should they support her chosen line of work, and hire her to clean their homes? No, that would be even worse. And what about the fact that Olivia isn't married? One of Olivia's friends hooks her up with a personal trainer (Scott Caan), even though he is already involved with a married woman, apparently because any relationship for Olivia is better than no relationship at all; his other relationship ...1