For British newspaper columnist Iris (KATE WINSLET), her romantic life has been a constant yo-yo of emotions thanks to her coworker and former lover Jasper (RUFUS SEWELL). He's now engaged to someone else, but persists in acting as if he and Iris are still a couple, behavior that confuses and has her in a funk.
Sharing her disdain for men at the moment is Amanda (CAMERON DIAZ), an American whose company creates movie trailers. While her business is a success, her love life is anything but, especially when her live-in boyfriend Ethan (EDWARD BURNS) finally confirms her suspicions that he has indeed been sleeping with another woman.
Wanting to swear off men and needing to get away from it all, the two women meet in an online chat where they agree to swap homes for two weeks. Immediately jetting off, Iris arrives in Hollywood and is immediately overjoyed by her swanky new digs as well as meeting Hollywood screenwriting legend Arthur (ELI WALLACH) and his younger composer counterpart Miles (JACK BLACK).
Across the pond, Amanda finds Iris' small and remote cottage quaint, but not exactly her style. Her decision to return, however, is interrupted when she meets Graham (JUDE LAW), Iris' brother who appears to her as a charming and handsome playboy. Seeing that he's intoxicated and probably won't remember her, she decides to sleep with him, a decision that results in both starting to have feelings for one another.
As the two women get used to their new temporary surroundings as well as the new men in their lives -- not to mention Graham's young daughters, Sophie (MIFFY ENGLEFELD) and Olivia (EMMA PRITCHARD) -- they try to figure out what will make them happy.