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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.
Charlie finds himself in an uncomfortable position when Jake takes off with the daughter of a former NFL player. Charlie's Mercedes seems to prove a boon to Alan's love life.
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.
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 and Alan throw a bachelor party for Marty once he proposes to Evelyn.
Alan gives Jenny relationship advice and Walden enters into a new project with a former employee.
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".
Alan helps Walden create a new identity in order to find a woman who isn't just after his money.
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 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.
Alan's ex-wife, Kandi wants him back and Walden helps Berta celebrate her birthday!
Jenny needs Walden’s help in getting a second date and Alan finds trouble with his girlfriend’s ex-wife.
Lyndsey's miffed that she doesn't have a key to the beach house. Meanwhile, Walden, Alan, Billy, and Herb share stories about women.
Walden and Alan try to keep up as Herb goes on a wild party binge at the beach house.
Walden is struggling to keep his two identities straight and Alan is home alone on Christmas.
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.
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?
Walden starts dating Rose regardless of Alan's warnings against it.
Jake gets caught cheating on his girlfriend, Tammy with her own daughter.
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.
Alan proposes to Lyndsey but ends up engaged to Judith. Meanwhile Jenny is afraid Brooke is breaking up with her.
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.
Alan and Walden have to deal with Zoey and Lyndsey's antagonism towards each other when a storm traps them all at the beach house.
Charlie’s illegitimate daughter suddenly appears and Alan is surprised not only by her existence but by how much she is resembles Charlie.
Walden, still reeling from his break-up with Zoey, buys a dog.
When Alan and Walden have a falling out, Alan has no choice but to seek refuge with Herb.
Walden hires an actress to play as his girlfriend. Missi returns to the beach house and so does Jake.
Zoey wants Walden to take on a more clean-cut look. Meanwhile, Alan and Lyndsey reconnect.
Walden attends a singles mixer for rich people and runs into Bridget. Alan gets worried when they begin talking about getting back together.
Lyndsey wants a serious commitment from Alan. Walden hides his identity to be with a rich older woman who uses him as boy-toy.
Missi, the daughter of a friend of Walden's, visits at the same time that Jake is on leave.
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 rushes to plan a surprise birthday party for Zoey.
Jenny moves into Evelyn’s home because of Walden’s feelings. Alan hooks up with Lyndsey even though she is seeing another man.
When Lyndsey's mother comes for a visit, Alan suggests she meets Evelyn. Walden is stuck hearing out iPhone app ideas from Jake and Eldridge.
Lyndsey and Alan try to add a little excitement to their love life.
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 finds himself in danger and must turn to Rose for help as a result if the affair between Alan and Lindsey.
Alan persuades Walden into inviting Lynda Carter over to dinner.
Having graduated high school, Jake and Eldridge face new urgency to face their adult lives.
When Walden feels Zoey is a bit stiff in the bedroom, Berta suggests a few of her marijuana brownies might loosen her up a bit.
Zoey comes back into Walden's life, which forces him into a making a deision between her and Rose.
Walden and Alan plan a double date with two attractive women, but Lyndsey gets jealous and ruins the evening.
Walden hopes to move things forward with Zoey, but Bridget's reappearance complicates matters.
Alan faces a number of shocking events after being released from the mental hospital.
When Zoey and Ava move in, Walden finds out if his commitment is up to the test. Meanwhile, Alan has his own challenges when he moves in with Lyndsey.
Walden knows Zoey won't be thrilled to learn Bridget is a partner in his new venture with Billy. Meanwhile, Alan and Lyndsey try to cope with their mothers dating each other and deal with Eldridge and Jake's questions.
Walden's former business partner shows up, looking to patch the rift between them.
Alan has trouble coping when Walden redecorates the house.
Walden's mother visits, dropping a secret about him as well as leaving Alan smitten.
Alan isn't thrilled when he learns of Lyndsey's adult film, and Walden hosts an impromptu party to lift his spirits.
After suffering a minor heart attack, Alan is visited by Charlie's ghost while in the hospital.
Zoey suspectsAlan doesn't really deserve all the love and attention he's getting following his release from the hospital.
Bridget has Walden served divorce papers, and then he meets a new woman who looks just like her.
Alan looks to reconnect with Lyndsey, while Walden seeks to move on from Bridget.
Walden hopes to start the process of winning back Bridget by taking her to dinner and seeks Alan's advice. Meanwhile, Jake gets ideas in his head when he learns Walden is a high school drop-out.
Walden has Alan come along for the ride when he tries to get his ex-wife, Bridget, to take him back.
Waldentakes Alan along to New York to see Kate at her show and reveal his true identity.
Following Charlie's funeral, Alan meets Internet entrepreneur Walden Schmidt.
Walden's miffed that Zoey didn't reciprocate after he blurted out "I love you" when his jet hit violent turbulence. Alan thinks Lyndsey is drinking too much.