
Chiropractor and single father Alan Harper lives in a beachfront house with divorced Internet billionaire Walden Schmidt, who bought the house following the untimely death of Alan's brother, Charlie. As they acclimate to their living arrangement, the tightly wound Alan finds himself taking on a mentor role with Walden, whose lifelong dependence on being taken care of has left him a bit naive. Despite his unsuccessful romantic history, Alan also tries to help Walden overcome his limited experiences with dating. Berta, a sharp-tongued, unapologetic housekeeper, is also featured in the series.

The guys run into Jake's former teacher (Alicia Witt) who became a stripper after a fling with Charlie; Charlie gives her a room and a job to try and help her out, but things get out of control.

Charlie unknowingly sleeps with an elderly man's (Orson Bean) hot trophy wife.

Alan's friendship with a gay single dad prompts both Alan and Charlie to re-examine their sexual identities.

Jake has a windfall when Charlie takes him to the track; Alan finds himself stuck at the Department of Motor Vehicles.