On the way back home, his newly acquired confidence faces a setback when Jake tells him that he is about to father a child with his girlfriend Megan. Although he is very upset, he calms himself down and arranges a meeting with Judith and Herb to tell them and face it as a family. During the meeting, Walden, who looks after a grown Milly, remarks that she looks a lot like Alan, deeply upseting Herb. Soon after, Alan also receives a letter from the IRS , informing him that he is being audited.
When Alan finds out that Lyndsey has left him for Walden, he completely loses his temper. Walden also asks him to move out, as it would be creepy if he stayed with them. They tell him that they put his stuff in a storage bin at the airport. Alan then tries to commit suicide through an overdose of CO , but fails miserably, as the engine of his car breaks down. After being rejected by his mother, he seeks shelter in his storage bin.
Just as he loses his last bit of hope, a beautiful woman named Veronica Hastings Nicole Steinwedell invites him to a glass of wine, immediately cheering him up. As the woman walks away to get the wine from her storage bin, Herb steps out of the dark in a trenchcoat. He then takes out a pistol and shoots Alan repeatedly. It is then revealed that Alan is still in the hospital and everything that happened was just a dream. When he actually returns home, he is confronted with Walden's new and modernized house decor.
Much to his sadness, it no longer reflects Charlie's home, prompting him to admit that he no longer belongs here. But when Walden asks him if this means he is going to move out, Alan declines immediately. Gary Busey guest stars as Alan's clinic roommate. Jake, in Alan's dream, discussing the plans of having his future son in a TV commercial. Jake, who heard his father talk about how rich Walden is, helps the latter where he can, fully intending to get paid for it.
He even advises Walden to ask her out, an offer that Zoey gladly accepts. When Jake asks his new "boss" if he owns a yacht, he tells him that he does not like displays of extreme wealth and, at the same time, reveals that he already got a private jet. He then proceeds to give Jake , frequent-flyer miles , having no use for them. On the night of the date, Alan recommends that Walden take off his wedding ring , as it indicates that he still has feelings for Bridget.
Walden gives the ring to Alan and decides to move on. During the date, he behaves oddly, mentioning his suicide attempt and the exact time that has passed since he and Bridget broke up, prompting Zoey to tell him that he is still in love with his ex-wife and isn't ready for dating yet. Proving this point, Walden calls Bridget after the date to tell her about it, only to hear her agree with Zoey. Meanwhile, Alan is desperate to earn some money and tries to set up a Ponzi scheme with different credit cards.
Just as he is about to ask Walden to loan him some money, Berta tells him that Walden likes him because he is the only one who does not want anything from him. Alan agrees with Berta and visits a pawn shop to make some money off of his old Gateway computer and the diamond cufflinks Evelyn gave him which turn out to be fake.
As Sid Jonathan Banks , the pawn shop owner, rejects the items, Alan presents him a vase which he hopes is worth a few bucks. After later receiving Walden's wedding ring calling it " My precious " that is made out of rhodium and platinum , he returns to the pawn shop and freaks out over its value. When he comes back to the house, he joins a sad Walden at the beach, who asks him for his ring. It is revealed that Alan did not pawn the ring, fully knowing that Walden would want it back in the end.
To Alan's shock, Walden decides to separate himself from the ring permanently by throwing it in the ocean. Alan storms into the water to search for it after Walden leaves.
Upon returning to the house, he confesses his intentions to Walden, who then tells him that he could have asked him for money, which he just gives away, as he does not believe in loaning it.
Alan declines the offer for the sake of their friendship and even agrees to pay rent. When Walden says he would have, Alan goes back into the ocean, being furious at himself. Just at that moment, Jake, who used Walden's frequent-flyer miles, calls from Paris, not knowing where he is.
Zoey Hyde-Tottingham-Pierce Title quotation from: Sid, the pawn shop owner, describing the items he has in his storage unit. As she is sceptical, he proves his intentions by signing his divorce papers in front of her. After that, the two start dating again and things seem to be going great. Walden helps Zoey to get her daughter enrolled in a private kindergarten and they even fly to Mexico in Walden's private jet. This idyll is disturbed when Bridget shows up at Walden's house to tell him that she wants him back.
The two go upstairs to have sex and, after pretending that he needs to use the bathroom and asking Alan for advice about what to do, Walden rejects her and suggests that she sign the divorce papers so that they can both move on with their lives because Alan did not want Walden to sell the house and have to move back into Evelyn's. Bridget is furious that Walden waited to tell her until she was half-naked in his bed and storms out. She then proceeds to drive her car into his house. Later, Bridget is shown standing on the deck, stalking Walden and Zoey.
Rose shows up unexpectedly and proposes to "teach" her, an offer that she hesitantly accepts. Walden, in an English accent, while flying to Mexico for dinner with Zoey.