Jim Winters (ANTHONY LaPAGLIA) is a New Jersey landscaper who's discovered that things don't always work out the way one would like or want. Five years after his wife's untimely death, he's still trying his best to raise his sons, but they don't fail to disappoint him.
The youngest, Pete (MARK WEBBER), has yet to graduate from high school and his underachieving results mean he'll have to attend summer school under the tutelage of Mr. Bricker (RON LIVINGSTON). Pete's older brother Gabe (AARON STANFORD) has a job, but isn't happy in his hometown and wants to leave, much to the chagrin of his girlfriend, Stacey (MICHELLE MONAGHAN).
The one bright point in Jim's life is an unemployed paralegal, Molly Ripken (ALLISON JANNEY), who's moved into the neighborhood to housesit for several months. They slowly develop a friendship that has the potential for something more, but Jim seems reluctant to move in that direction. When Gabe drops the bombshell that he's moving out of town, Jim and everyone else must deal with the sudden news.