Season synopsis
Contains spoilers for this season and earlier seasons.
Season 8 finds Charlie trying to move beyond Chelsea while his household keeps drawing him back into romantic trouble. He dates Michelle, an older dermatologist, but retreats after learning about her adult daughter; he also becomes involved with Courtney, a former girlfriend who returns after prison and exploits his attraction to her. Charlie and Alan’s home is increasingly shared with Alan’s girlfriend Lyndsey and her son Eldridge after their house burns, complicating Alan’s already unstable relationship with Melissa.
Charlie and Courtney eventually tire of their relationship and split up, after which he sinks into a depressed stretch before finding comfort in Rose, the neighbor who has long pursued him. He becomes convinced that Rose is married, watches her and eventually starts an affair with her despite the apparent obstacle. Alan’s business troubles meanwhile turn into a Ponzi-style investment scam that draws in family members, setting up the finale’s collision between Rose’s secret and Alan’s scheme.
In the finale, Alan goes to Rose’s house intending to blackmail her, but discovers that her supposed husband Manny is a mannequin and that Rose has been deceiving Charlie. Rose offers money to cover Alan’s scam; he accepts it and repays the people he cheated. Charlie, still unaware of the deception, says he plans to propose in Paris and leaves with Rose for a weekend away.