Charlie borrowed money from Alan and on the day he is supposed to pay him back, Alan goes to ask Charlie for the money. He again finds Charlie in bed with a beautiful woman. After Charlie shoos him out and assures him he'll get the money for him later that day, the woman asks if Charlie is really out of cash and Charlie tells her not to worry, that he has plenty of hooker money.
Charlie tries to help Jake's former teacher, who became a stripper after dating him, but things go from bad to worse when she has a religious conversion.
When Judith kicks Herb to the curb, Alan comes knocking; Jake is sent to stay with a less-than-willing Charlie for three months during Judith's meltdown.
Alan tries to escape Judith's grasp as Charlie and Herb go on the prowl to pick up women. They later end up going back to Herb's hotel room with two prostitutes, where Herb declares his love for Judith and races over to win her back.
Charlie's new girlfriend Chelsea asks him to spend the night at her place, which puts Charlie well outside of his comfort zone, while Alan tries to enforce a punishment on Jake initiated by Judith for mooning a group of girls.
Charlie finds himself in an uncomfortable position when Jake takes off with the daughter of a former NFL player. Charlie's Mercedes proves a boon to Alan's love life.
Evelyn offers to pay for Jake's college education, and Alan becomes listless because he has no compelling reason to work anymore, while Jake discovers a hidden talent in the culinary arts that may allow him to bypass college altogether.
After Chelsea discovers a nude picture of another woman on Charlie's cell phone, he blows off steam by going out for a night of drinking with Alan, Herb and his neighbor.
Charlie mourns the loss of his bachelor pad as he reluctantly allows Chelsea to move in. Meanwhile, Alan discovers there is no longer much space left in the house for him.
Charlie starts to question his relationship with Chelsea when he hears that Mia is back in town. Meanwhile, Judith goes into labor and Charlie, Alan and Herb rush her to the hospital, on the sixth season finale.
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