S1, Ep7. Jake sees a butterfly tattoo on the firm bottom of a surfer-chick friend of Charlie's and draws a picture of it for school. Of course, this enrages Judith until she becomes very good friends with the woman herself.
S1, Ep8. After being tricked into helping Alan and Judith produce Jake's classroom musical, Charlie is flattered to find out that the kids know all the words to his jingles.
Alan is blind-sided with divorce papers from Judith, causing strife which results in Charlie, who refuses to deal with the pre-pubers without a snootful, having to produce the play on his own. Jake is crushed when he realizes that a reconciliation between his parents may never happen. S1, Ep9. Charlie wants to dump a female friend to whom Jake has grown attached. Alan and Rose bond over a game of Scrabble. S1, Ep Thanksgiving winds up being the least thankful day of the year for Charlie, who has to bribe various members of his household to even come to a traditional turkey dinner.
Not only are the usual feuds in evidence leading to a turkey-carving right out of "Psycho" but Judith's parents are actually sympathetic to Alan and hostile to their own daughter for her "fling" with lesbianism. Seeing Judith's new look and boyfriend prompts Alan to realize that if he wants to get back into the dating scene, he will need to change his look also. Berta brings her 16 year old granddaughter to work. She poses issues for the men. Charlie tries to nurse Alan back from the flu because he needs him for a double date with sisters.
Charlie's accountant Stan tries to make Charlie understand his desperate financial situation. Charlie falls for a seemingly crazy woman named Frankie--against Alan's advice. Now that Frankie has tricked the Harpers into taking her and her daughter Joanie in, she explains that Bob's parents want her declared mentally incompetent in order to get custody. Charlie wants to dump her, but Alan insists on taking them both in. Jake doesn't enjoy the 8 year old's 'romantic' attention.
Charlie hates the consolation kisses and compliments, and is stunned when Frankie prefers intimacy with Alan. Charlie rightly warns him he's just falling for his 'damsel in distress', but warns her not to hurt his kid brother. Charlie is offended when Alan chooses his married, responsible cousins as Jake's guardians.
Charlie's old flame, Jill, comes for a visit, she had an operation and is now called "Bill". Then Evelyn starts dating Bill. Jake plays electric guitar all day long and doesn't want to do anything else. Alan and Charlie can't figure out why. Jake refuses to discuss anything with anyone, including his grandmother and even a psychologist.
Charlie tries to seduce Alan's divorce lawyer, Laura, and her assistant. He sleeps with Laura and they decide not to tell Alan anything since it's unethical, considering that Charlie is a participant in the case. Charlie notices that Alan sleepwalks and tries to find out what's causing it and how to deal with it. He asks for help from their mother, Evelyn, and Jake's psychologist, Dr.
Linda Freeman. Jake repeats something Charlie says to Judith. Then Judith refuses to let Alan take Jake for the weekend. Alan tries to talk to Judith, but encounters resistance from Judith and her friends.
It's up to Charlie to set things right. Charlie is sure he isn't ready for fatherhood after a year of trying to raise Jake, so he opts to have a vasectomy. Walden is conflicted when a friend's hot daughter comes to visit, but the problem solves itself when Jake arrives for a surprise visit. S10, Ep5. After a series of bad double date setups with Alan and Lyndsey, Walden meets a new woman--Charlie's ex, Rose.
S10, Ep6. Just as Walden considers making a big move in his relationship with Rose, Zoey re-enters the picture and asks him to take her back. S10, Ep7. S10, Ep8. Alan loses Lyndsey over his refusal to make a long-term commitment, while Walden becomes a "boy toy" for a rich older woman who has no idea that he's a billionaire. S10, Ep9. Alan's second ex-wife, Kandi, could spoil Alan's new long-term relationship with Lyndsey. Meanwhile, Walden tries to celebrate Berta's birthday.
S10, Ep Walden creates an "Everyman" persona and finds a woman who isn't interested in him because of his money. While Walden takes a job as a Christmas tree salesman as part of his ruse, he gets a billion dollar business proposal from Mark Zuckerberg. Meanwhile, Alan finds himself completely alone at the beach house for the holidays. While Walden's health and other bedroom issues begin to suffer as a result of living a lie, he gives Alan , dollars to "invest" in Kate's fashion line.
Alan, Walden, Billy, and Herb spend the night out together commiserating over their exes after Lyndsey dumps Alan one more time. Alan is alarmed when he discovers that Jake's new girlfriend is almost twice his age, has three children, and owns a tattoo parlor.
Alas, she only wants friendship, still prefers 'Sam' and now has just a busy calendar as Walden, so no next date can be booked. For once, Alan decides to 'spoil' Lyndsey on Valentine's Day by booking a hotel suite he can't really afford. But pubic grooming on himself goes so bad she has to drive him to hospital instead. Rose is unsuspecting Kate's new business partner, who lures her to China.
Walden goes to a mixer to find a woman but runs into his ex-wife Bridget instead. After Alan and Walden fight over a toaster, Alan moves out and goes back to his old house to live with Herb. Alan and Walden take Herb out to take his mind off of his troubles, but his partying quickly spirals out of control. Tammy comes after Jake after he cheats on her with her 18 year old daughter.
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