After Jake talks Walden into asking out a woman he meets at a supermarket, Alan considers hocking Walden's incredibly expensive wedding ring to get out of debt.
Upon his return from the "stress clinic," Alan finds out that Jake got his girlfriend pregnant, Walden and Lyndsey are sleeping together, and he has to move out immediately
Still emotional after Charlie's death and jealous over Walden's ability to pick up hot single women, Alan takes a break from reality and channels his inner Charlie.
Walden hires Evelyn as his interior decorator, but Alan is convinced that she just wants to take advantage of him sexually. Meanwhile, Alan inherits Charlie's journal, and Jake has a crush on his tutor, but she has a crush on Walden.
Alan convinces Walden to see Charlie's old shrink after he gets his divorce papers from Bridget, but his spirits are soon lifted after he meets a lesbian who looks like her
Alan begins working on getting Lyndsey back, but his days at Walden's place may be numbered after Walden hooks up with Charlie's gold-digger ex girlfriend, Courtney.
Walden buys Charlie's house and hires Berta as his live-in housekeeper, forcing Alan to move back in with his mom. However, Alan sees an opportunity to come back when Walden asks for advice about getting his wife back.
After the death of Charlie Harper, Alan faces the reality of moving out of his brother's beach house - until he meets a depressed Internet billionaire whose wife just left him.