In "The Squat and the Hover", After running into Bridget with a date at the movies, Walden heads to the bar with Alan to drown his sorrows. There, they meet a woman named Danny who looks strikingly like Bridget, although she is a lesbian and accompanied by her partner, Kiki. Walden kisses Alan, trying to win Danny and Kiki's favor by convincing them he and Alan are also gay. The four head back to the house where he eventually confesses to Danny that he is not really gay and only wanted to spend time with her because she reminds him of his soon-to-be ex-wife. At the end, Alan confesses to Walden that he only sent him to Dr. Freeman because he did not want to move out again and that he understands if he has to go. Walden then tells him that he is going to stay, as he took the doctor's advice to sort out his problems instead and states "How could I leave behind my best friend?".
In "Slowly and In A Circular Fashion", When an investment made by Walden goes bad, his ex-wife Bridget and mother Robin, the other two Board Members of his company, Walden Loves Bridget Enterprises, decide to terminate Walden's presidency and make decisions by taking advantage of their vote share. After consulting with Zoey, Walden decides to use his power as the Founder of the company to add Alan as a member of the Board and use his vote to equalize the voting rights thus giving him the tie-breaking vote. Bridget and Robin, finding no loopholes out of this, try to convert Alan. Ultimately, Alan decides to remain loyal to Walden. Once reinstated, Walden uses his presidency powers to rename the company to Walden Loves Alan Enterprises. Alan finally enjoys success, receiving a director's honorarium of $50,000 a year and Walden agrees to add Alan's name on the deed of the house in order to ensure his loyalty.
In "I Scream When I Pee", Walden was surprised to learn of Alan's second marriage, especially to an attractive young woman. He does find amusement in Alan's relationship troubles when Lyndsey finds the pictures of them.
In "The Straw In My Donut Hole", Everyone but Zoey is being incredibly and unusually nice to Alan when he gets home from the hospital after his non-heart attack: Walden lets him stay at the beach house. Unfortunately, Alan's visit to his cardiologist produces a clean bill of health and the prospect of everyone treating him normally again (meaning, badly). Alan is left with one response: pretend that the news was bad and he might need a heart transplant. However, when Zoey gets proof about Alan's misbehavior, Alan, awaiting his punishment for misbehaving, stupidly attempts (and fails) to fake another heart attack and is left lying on the floor until his shame goes away. Despite this, Alan continues to live at the beach house.
In "That's Not What They Call It In Amsterdam", when Walden starts dating Rose, Alan warns him the dangers of how she used to stalk Charlie, but Walden doesn't listen to him. It is clear that Alan really is his friend and is living there to protect him and not (only) leach off of him.