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Walden finds himself alone without Alan and tries to get him back, but Herb is overjoyed with having Alan keep him company and does not want him to go back, and thus isolates Alan from Walden. However, being in a committed relationship with Lyndsey, Alan tries to do the right thing by turning down Kandi and telling Lyndsey. While Lyndsey is anxious to go out, Alan has an accident finishing his surprise and ends up in the hospital.
Jake comes home on leave and announces that he is going to be stationed in Japan for at least a year, which saddens Alan. Ending up in bed, they seem to make a close renewed connection, however, she gets more and more controlling. Zoey refuses and breaks up with Walden revealing she has met someone else. Stressed about how he is going to do it, Walden spends the next three weeks at Kate's apartment gorging himself with junk food, and becoming fat. Alan begins to feel alone and miserable, until a less-than-willing Berta comes to seemingly comfort him.
Despite her appearance, Tammy is a good-hearted woman, who knows how Alan feels about her and her relationship with Jake. Alan and Walden, having partied way too hard, tell Herb to slow down and go back to his home, but Herb gets offended and leaves. They rush him back to Meghan's place, so his relatives won't cut her out of Victor's will for having an affair. The first threesome involves Walden, but after he can't go through with it and starts crying over loosing Zoey, Alan and Lyndsey move on to Alan's version of a threesome.
Going to a mixer for rich singles, Walden runs into his ex-wife Bridget. They also run into Herb, who reveals that Judith left him after she caught him cheating on her with his receptionist. This convinces Alan to commit to Lyndsey and the two reconcile, finally becoming engaged despite Alan noting that he does not have enough money for even a deposit on a ring. They later find him in a motel, very high, wearing body paint and a diaper.
She and Alan have revenge sex, and Alan wakes up the next morning in a cheerful mood. Alan remains suspicious of Rose, thinking she is out to get Walden and walks in on the two engaged in a bondage game, thinking Rose has manipulated Walden.
Walden doesn't take his break up from Zoey pretty well and releases his anger on Alan, Robin, and his business partner Billy. Predictably, Alan's car breaks down on the side of the road. They both set down Alan and Berta and tell them that it is best for the household that they leave. He makes everyone Bloody Marys, and both Walden and Alan wake up hung over the next day while Herb is throwing yet another wild party at the house. Missi is revealed early-on to be very talkative, not giving others a chance to get a word in.
Meanwhile, Walden is despondent over his breakup with Kate and Billy gets dumped by Walden's ex-wife Bridget. On the deck, Walden and Tammy end up making out while talking about relationships. Touched, Alan reluctantly give Jake some more money. At Pavlovs, Walden and Tammy have a heart-to-heart talk over her parenting and Walden believes Ashley and Jake will be happy together since Jake and Tammy were good together. However, it is revealed that Walden imagined his reconciliation with Bridget as the scene cuts back to him at the mixer behind her.
Walden takes Alan to Pavlov's to cheer him up. When Herb and Walden begin to argue over Alan, Alan decides to go back to Walden as he needs him more.
They begin a short affair, but as Jake is leaving to return to base, Missi reveals to him that she has a boyfriend. To help save Herb, they reluctantly call Judith to take him back. Unfortunately, Walden spills the beans during dinner and Alan and Jake have a falling out over Jake's decision to get married. Rose seemingly understands and accepts the decision, but as Walden begins to feel comfortable, Rose sends her ferrets to attack him.
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