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Sep 22, 200822 min
In the 6th season opener, Charlie runs into an ex-girlfriend and a child who bears a striking resemblance to Charlie.

Sep 29, 200822 min
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.

Oct 6, 200822 min
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.

Oct 13, 200821 min
Alan is sure that things will turn bad when Charlie starts dating his receptionist.

Oct 20, 200822 min
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.

Nov 3, 200822 min
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.

Nov 10, 200822 min
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.

Nov 17, 200822 min
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.

Nov 24, 200822 min
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.

Dec 8, 200821 min
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.

Dec 15, 200822 min
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.

Jan 12, 200920 min
Charlie and Jake fight for the affections of a waitress, while Alan fights sexual tension with his receptionist.

Jan 19, 200922 min
Judith is pregnant with a baby girl and Alan is convinced he is the father.

Feb 2, 200921 min
Melissa doesn't think Alan's family appreciates him, so she asks him to move in with her and her mom.

Feb 9, 200921 min
Charlie ends up in couples counseling.

Mar 2, 200920 min
Charlie has to remove a half-naked woman from his bedroom before Chelsea arrives.

Mar 9, 200920 min
Charlie's admission that he's in love with Chelsea gets a surprising reaction from her

Mar 16, 200921 min
Chelsea's illness gives Charlie a chance to prove he can take care of her, but also yearning to run away from the situation.

Mar 30, 200920 min
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.

Apr 13, 200922 min
Charlie's desperate to make sure Chelsea and Evelyn don't befriend each other following their first meeting.

Apr 27, 200921 min
Chelsea is asked by Alan to arrange a blind date between he and her new friend, unaware that her new friend is Rose.

May 4, 200920 min
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.

May 11, 200920 min
Alan and Chelsea become best buds, and Charlie decides to take advantage of the situation.

May 18, 200921 min
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.