Walden ends up on a date with a clumsy woman which extends his time with her. Alan finds himself involved with a woman who shares too much information with him.
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.
Alan persuades Walden into inviting Lynda Carter over to dinner.
Alan spends time with Lyndsey’s boyfriend in hopes of discovery why Lyndsey likes him so much. Walden encourages Jenny to take her acting career more seriously.
Walden starts partying with Jenny and her friends, eventually culminating in a massive orgy with them, Berta, and several people from the beach. Alan and Lyndsey's affair encounters some problems.
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 and Alan try to keep up as Herb goes on a wild party binge at the beach house.
When Alan and Walden have a falling out, Alan has no choice but to seek refuge with Herb.
Walden attends a singles mixer for rich people and runs into Bridget. Alan gets worried when they begin talking about getting back together.
Valentine's day is approaching, and Alan wants to make it special for Lindsay. Unfortunately, his plans go awry at the last minute. Kate is back in town and wants to meet up with Walden, but can he convince her to take him back?moreless
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
Walden is struggling to keep his two identities straight and Alan is home alone on Christmas.
Alan helps Walden create a new identity in order to find a woman who isn't just after his money.
Alan's ex-wife, Kandi wants him back and Walden helps Berta celebrate her birthday!
Lyndsey wants a serious commitment from Alan. Walden hides his identity to be with a rich older woman who uses him as boy-toy.
Walden hires an actress to play as his girlfriend. Missi returns to the beach house and so does Jake.
Zoey comes back into Walden's life, which forces him into a making a deision between her and Rose.