Terry Wolfmeyer (JOAN ALLEN) is a bitter, middle-aged woman who's trying to drown her anger in booze and emotional detachment. She's angry because her husband, Gray, has seemingly run off with his younger secretary, thus leaving Terry to deal with their four daughters who test her resolve every day.
There's Hadley (ALICIA WITT), the oldest who cares the least for her mother and is off at college. Emily (KERI RUSSELL) isn't eating anything since she wants to become a ballet dancer, much to her mother's dismay, which similarly holds true for Andy (ERIKA CHRISTENSEN) who's decided she's not going to college but instead is going to get a job. Then there's 15-year-old Popeye (EVAN RACHEL WOOD) who's making some sort of video project about violence and anger when not hanging out with Gordon (DANE CHRISTENSEN), a guy she likes romantically despite the fact that he says he's gay.
Compounding Terry's issues and feelings is Denny Davies (KEVIN COSTNER), a former pro baseball player and current alcoholic who hosts a radio talk show when not hawking baseball paraphernalia sporting his signature. The laidback Denny initially just wants a drinking buddy and Terry begrudgingly complies, but the two start developing feelings for each other as the months and years pass.
In the meantime, Terry must put up with her daughters and their various decisions about their lives. That includes Andy taking a job working for Denny's radio show producer Shep Goodman (MIKE BINDER) who wants nothing to do with her until he lays his eyes on her beauty. He not only gives her a job at the station, but he also becomes her boyfriend, much to Terry's horror. From that point on, and as she tries to figure out her relationship with Denny, Terry must deal with that and various other unexpected developments and decisions that arise in her life.