
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.

Charlie and Alan try to prepare Jake for his first day of junior high.

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.

After taking a loan from Evelyn, Alan is guilted into double-dating with her, her new romantic interest and his daughter.