Ned lived a happy life growing organic vegetables on a farm with his hippie girlfriend and his dog named Willie Nelson, but an unadvised incident with marijuana at a farmer's market lands him in jail. When he gets out of jail, he is off to live with his sisters. While Ned is still happy, his sisters are much less so after he manages to screw up one marriage, one job opportunity, one budding relationship and one domestic partnership. He sees those problems as breakdowns in communication, but his sisters see him as an idiot.

In Manhattan, Sofia's an attorney and Tom's a cook who has a hard time holding a job. When their first child is born, they agree that she'll be a full-time mom and he'll get a promotion. When he gets fired, he takes a job in Ohio working at the ad agency where her father is assistant director. Tom's assigned to report to Chip, a competitive, hard-driving guy who's in a wheelchair and who's Sofia's ex-boyfriend - from high school. Chip still carries a torch for her, so he connives to make Tom's work life miserable. As Tom's frustrations mount, it may be that Sofia will take Chip's side. Is Tom doomed to fail yet again?