Olivia (JENNIFER ANISTON), Jane (FRANCES MCDORMAND), Franny (JOAN CUSACK) and Christine (CATHERINE KEENER) are longtime friends who couldn't be any more different. While Franny wonders what to do with the riches she's attained through her successful husband Matt (GREG GERMANN), Olivia works as a maid, cleaning others' homes -- such as that of unemployed Marty (BOB STEPHENSON) -- after giving up a career of teaching.
Christine writes scripts with her husband David (JASON ISAACS) but their marriage is anything but a hit. And wildly successful fashion designer Jane is completely unhappy with her life, a viewpoint that befuddles her husband Aaron (SIMON McBURNEY) who runs his own organic bath company.
While Christine and David try to work around their home expansion, Franny tries fixing up Olivia with her physical trainer, Mike (SCOTT CAAN). He's just interested in sleeping with her, but gets her thinking about changing careers again, although she gets mad at Franny when she won't help finance that endeavor. Meanwhile, Christine continues with her belief that Aaron is gay, a point reinforced when he starts to hang out with Aaron (TY BURRELL), a married man who finds a kindred spirit in him.
As the various friends sort through their own and the others' personal issues, the issue of monetary differences repeatedly comes into play regarding how the men and women interact with each other.