Another year of bachelorhood brought many new adventures for roommates Walden Schmidt and Alan Harper. After his girlfriend turned down his marriage proposal, Walden was thrown back into the dating world in a serious way. He got invited to a threesome with Alan and his girlfriend, Lindsey, and then created a false identity in order to find a girl who wasn't after his money.
When Walden's old friend Missy came to visit, Jake fell so head-over-heels for her he went AWOL from the Army. The guys may have thought things were going to slow down once Jake got transferred to Japan, but they're about to be proven wrong when a niece of Alan's, who shares more than a few characteristics with her father, shows up at the beach house.
Charlie Sheen and Jon Cryer star along with young Angus T. Jones as three males from two generations, each learning what it really means to be a man. Charlie is a well-to-do bachelor with a house at the beach, a Jaguar in the garage and an easy way with women.
His casual Malibu lifestyle is interrupted when his tightly wound brother, Alan, who's facing a divorce, and Alan's son, Jake, come to stay with him. Together, these two and a half men confront the challenges of growing up - finally. Complicating matters are the brothers' self-obsessed, controlling mother, Evelyn (Holland Taylor), and Alan's estranged wife, Judith (Marin Hinkle).