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.
Alan and Chelsea become best buds, and Charlie decides to take advantage of the situation.
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.
Chelsea is asked by Alan to arrange a blind date between he and her new friend, unaware that her new friend is Rose.
Charlie's desperate to make sure Chelsea and Evelyn don't befriend each other following their first meeting.
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.
Chelsea's illness gives Charlie a chance to prove he can take care of her, but also yearning to run away from the situation.
Charlie's admission that he's in love with Chelsea gets a surprising reaction from her
Charlie has to remove a half-naked woman from his bedroom before Chelsea arrives.
Charlie ends up in couples counseling.
Melissa doesn't think Alan's family appreciates him, so she asks him to move in with her and her mom.
Judith is pregnant with a baby girl and Alan is convinced he is the father.
Charlie and Jake fight for the affections of a waitress, while Alan fights sexual tension with his receptionist.
Charlie finds himself re-examining his wild ways when an old friend dies and begins to feel that his time on Earth may be drawing to a close.
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.
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.
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.
Alan tries to get away from Judith. Meanwhile, Charlie and Herb go out on the town.
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.
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.
Alan is sure that things will turn bad when Charlie starts dating his receptionist.
Alan, Jake, and Charlie all decide to try new things: Alan is dating more than one woman, Charlie learns to cook, and Jake experiments with beer.
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. MORE -LESS
In the 6th season opener, Charlie runs into an ex-girlfriend (Rena Sofer) and a child who bears a striking resemblance to Charlie.
