Walden gets a new toy, but soon finds his future at Nicole's startup may be limited. Meanwhile, Alan can't stay away from Lyndsey and Larry and begins dating Larry's sister.
Alan proposes to Lyndsey but ends up engaged to Judith. Meanwhile Jenny is afraid Brooke is breaking up with her.
Alan is upset when he discovers that Lyndsey broke up with Larry and kept this information from him. When Walden’s masculinity is questioned he decides to prove he is a real man.
Walden and Alan throw a bachelor party for Marty once he proposes to Evelyn.
Walden is feeling frustrated because Nicole has no time for him due to a software project, so he offers to help her with it. Larry convinces Alan to go on a blind date, which Larry arranges.moreless
Alan gives Jenny relationship advice and Walden enters into a new project with a former employee.
Jenny needs Walden’s help in getting a second date and Alan finds trouble with his girlfriend’s ex-wife.
Walden finds himself in danger and must turn to Rose for help as a result if the affair between Alan and Lindsey.
Walden and Alan plan a double date with two attractive women, but Lyndsey gets jealous and ruins the evening.
Walden finds Berta lying on his bed after injuring her and back suggests that it may be time for her to retire. Berta quits working and the guys begin the search for a new housekeeper.moreless
Jenny moves into Evelyn’s home because of Walden’s feelings. Alan hooks up with Lyndsey even though she is seeing another man.
Charlie’s illegitimate daughter suddenly appears and Alan is surprised not only by her existence but by how much she is resembles Charlie.
Walden meets another young, drunk girl and drives her home where her grandmother receives them. An unexpected turn of events make Walden find her attractive while Jake gives Alan big news about his brand new job.moreless
Alan tries to get over the break up, and Walden decides to help him with that and borrows his credit card to him. Alan gets a change of looks and meets a new lady "friend".moreless
After some time of thinking and decision making Lindsey decides to break up with Alan leaving him devastated. After a short period of denial Alan finally accepts the break up and takes his own little revenge on her.moreless
Jake gets caught cheating on his girlfriend, Tammy with her own daughter.
Walden attends a singles mixer for rich people and runs into Bridget. Alan gets worried when they begin talking about getting back together.
Lyndsey's miffed that she doesn't have a key to the beach house. Meanwhile, Walden, Alan, Billy, and Herb share stories about women.
Waldentakes Alan along to New York to see Kate at her show and reveal his true identity.
As Alan gets increasingly comfortable living in the beach house. Walden wants to invest in his girlfriend Kate's fashion career, without her discovering that he is billionnaire Walden Schmidt rather than broke Sam Wilson, as he has led her to believe. The stress of this deception begins to affect Walden's health.moreless