In episode 73, Charlie has no trouble returning to his reckless, bachelor lifestyle when Alan moves out of the house. Alan breaks down after a recent divorce from Kandi, and Charlie calls their mom out of desperation to help out Alan. Charlie spills the beans to Alan, in episode 74, why he didn’t marry Mia—for the reason that she wanted Alan and Jake out of the house. Alan, however, finds that something is not right in his logic. Meanwhile, Charlie and Alan adjust with their noisy neighbor. In episode 75, Charlie tries to win the affection of Dottie, a beautiful woman he recently met. But later in the episode, he almost drowns—pretty convinced that he saw his dead father. In episode 76, Alan tries to win custody over the dog that he and his now former wife Kandi owned—by trying to his former wife’s lawyer and even running to Judith to help him steer Kandi to a mean attorney.

Alan, in episode 77, is exhilarated by the fact that when Judith remarries, he is no longer entitled to pay alimony. Alan seeks the help of Charlie when Jake disapproves of his mother’s fiancé, which might be a possible hindrance to the possibility of the new marriage. In episode 78, Charlie dates a woman whose whole being is similar to his mother’s—only he doesn’t seem to spot likeness. In episode 79, Naomi, Berta’s daughter, is pregnant. Berta brings Charlie along when she confronts the child’s father in a rowdy community. Alan, on the other hand, confesses a secret fetish once he bonds with Naomi. Insomnia gets to Alan in episode 80. After a visit to his psychiatrist, he discovers that his insomnia is caused by sibling jealousy towards Charlie and how he is unable to just face life with a breeze. After promising Jake not to, Charlie gets intimate mom of the girl that Jake likes—and of course, Jake gets back at him.

In episode 81, Charlie reaches his limit when he gets fed up with Alan’s leaching off—reaching the tipping point during their double date. Later in the episode, Alan explains why he’s borrowing huge sums of money. Also, for the first time, Jake is left home alone. Emotions spike up, in episode 82, when Lydia wears a rude attitude towards Berta while Charlie faces a dilemma. Kandi, on another note, tries to stop Alan from selling the condo they shared. In episode 83, the whole family and Charlie’s friends put a twist on Charlie’s Christmas Eve date. Evelyn finds out who the date is, and tries to prevent Charlie and the girl from having sex. Alan becomes the peacemaker when Judith gets angry with Herb finding Judith’s breasts appealing. Jake tells Charlie that he’s heard his mother making love with her fiancé, Herb in episode 85. The knowledge reminds Charlie of a repressed memory of his. He then runs to Rose to ask for help.

Episode 86 starts off with Charlie setting Alan up with the new neighbor Danielle—hoping it will help Alan move out of the house. Eventually, Charlie’s plan backfires because he seems to want Danielle for himself as well. In episode 87, Rose moves to London and Charlie is astounded with his own reaction upon hearing the news. He later realizes that he let go of the best woman in his life. In episode 88, Charlie’s young girlfriend takes the guys to a new club. Charlie and Alan are surprised to find out that they are already considered “old” by her friends. Charlie then ends up depressed by this health, but Alan, being his brother, always has an idea to cheer him up.

Evelyn shares to Alan and Charlie how sad she feels that there were no people who were crying at her friend’s funeral and the two guys, on the other hand, tell her that that could be her fate as well in episode 89. She tries to prove them wrong as the episode progresses. In Episode 90, Alan spends time with Jake, realizing that his son’s childhood years are about to end. Kandi aspires for an acting job that Alan’s desire to have kids can possibly hinder.

In episode 91, Alan is excited in handing Judith her last alimony check. Charlie encounters Herb’s sister, Myra, discovering that they share the same problem—how they don’t like Judith. Episode 92 is actually just a continuation of the previous one. Alan embraces the fact that Judith is getting married soon, and Charlie and Myra develop more common interests. Alan and Charlie assess their sexual preferences, in episode 93, after Alan becomes friends with a gay man, Greg. Jake, on the other hand, likes Greg’s daughter. In episode 94, Alan wants to go to the DMV and so he asks Charlie to help Jake out with his book report. Charlie agrees, but instead takes Jake to the race track with him. Alan gets conned at the DMV. In episode 95, Charlie gets the shock of his life when the handyman he hired in his house tries to win the affection of his girlfriend, Chloe. Alan is simply apathetic to Charlie’s dilemma. In the final episode of the season, Evelyn’s new boyfriend, Teddy, takes Alan and Charlie to Las Vegas. They both vent out their feelings about their mother dating, and different men coming in and out all the time. In the end, they decided that Teddy is a great man.