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24 Episodes 2008 - 2009
Season 6 of the CBS sitcom earned Jon Cryer an Emmy Award for Outstanding Supporting Actor in a Comedy Series, while Charlie Sheen snagged a nomination for Outstanding Lead Actor. The series' first acting Emmy coincides with a few firsts for the characters, notably when Charlie (Sheen) attempts to cook, Alan (Cryer) tries dating two women at the same time and Jake (Angus T. Jones) takes a swig of beer. Meanwhile, Charlie runs into an ex-girlfriend (Rena Sofer) whose son bears a striking resemblance to him; Alan loans Charlie money, but takes things a step too far when he tries to get the cash back; Charlie tries to help Jake's former teacher (Alicia Witt), who became a stripper after dating him; Alan considers early retirement when Evelyn offers to foot the bill for Jake's college education; and the house gets a new roommate. Guest stars include Jennifer Bini Taylor, Michael Clarke Duncan, Kelly Stables, Carol Kane and Ryan Stiles.
Episode 1
Mon, Sep 22, 2008 30 mins
In the sixth-season opener, Charlie runs into an ex-girlfriend whose son bears a striking resemblance to him.
Episode 2
Mon, Sep 29, 2008 30 mins
Alan loans Charlie money, but takes things a step too far when he tries to get the cash back.
Episode 3
Mon, Oct 6, 2008 30 mins
It's a series of firsts for the guys as Charlie attempts cooking, Alan tries dating two women at the same time, and Jake takes a swig of beer.
Episode 4
Mon, Oct 13, 2008 30 mins
Charlie romances Alan's receptionist, and Alan has a bad feeling about the outcome.
Episode 5
Mon, Oct 20, 2008 30 mins
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.
Episode 6
Mon, Nov 3, 2008 30 mins
Alan jumps at another chance with Judith after she sends Herb packing.
Episode 7
Mon, Nov 10, 2008 30 mins
Alan tries to dodge Judith, who has become a little too needy, while Charlie and Herb go out in search of women.
Episode 8
Mon, Nov 17, 2008 30 mins
Charlie's new flame wants him to spend the night at her place. Meanwhile, Alan attempts to impose a punishment on Jake.
Episode 9
Mon, Nov 24, 2008 30 mins
Jake disappears with the daughter of Charlie's new neighbour, a former NFL player, and Charlie scrambles---and fumbles---to cover for him. Meanwhile, Charlie's Mercedes helps Alan get a hot date.
Episode 10
Mon, Dec 8, 2008 30 mins
Alan considers early retirement when Evelyn offers to foot the bill for Jake's university education.
Episode 11
Mon, Dec 15, 2008 30 mins
When Charlie's old friend and fellow womaniser dies, Charlie takes a hard look at his own lifestyle.
Episode 12
Mon, Jan 12, 2009 30 mins
Charlie and Jake compete to win the affection of a waitress; Alan senses sexual tension between him and his receptionist.
Episode 13
Mon, Jan 19, 2009 30 mins
Judith is pregnant, and Alan suspects he's the father. Meanwhile, Jake is in a foul mood.
Episode 14
Mon, Feb 2, 2009 30 mins
Melissa doesn't think Alan's family appreciates him, so she asks him to move in with her and her mother.
Episode 15
Mon, Feb 9, 2009 30 mins
Charlie ends up in couples counselling.
Episode 16
Mon, Mar 2, 2009 30 mins
A flustered Charlie tries to get a half-naked woman out of his bed when he learns Chelsea is coming to see him.
Episode 17
Mon, Mar 9, 2009 30 mins
Charlie declares his love to Chelsea, but he isn't prepared for the response he receives.
Episode 18
Mon, Mar 16, 2009 30 mins
When Chelsea gets sick, Charlie takes care of her---but he also tries to resist the urge to flee.
Episode 19
Mon, Mar 30, 2009 30 mins
Charlie blows off steam by sharing a drunken night with Alan, Herb and his neighbour after Chelsea discovers nude photos of another woman on his mobile phone.
Episode 20
Mon, Apr 13, 2009 30 mins
Evelyn meets Chelsea for the first time, and Charlie tries to keep them from becoming friends.
Episode 21
Mon, Apr 27, 2009 30 mins
Alan lets Chelsea arrange a blind date for him and her new friend, not knowing the friend is Rose.
Episode 22
Mon, May 4, 2009 30 mins
Chelsea moves into the house, and Alan feels like he's being pushed out.
Episode 23
Mon, May 11, 2009 30 mins
Alan and Chelsea bond, and their time together gives Charlie a needed break to do the things he loves doing on his own.
Episode 24
Mon, May 18, 2009 30 mins
In the sixth-season finale, Mia comes back to town, and her return makes Charlie reconsider his feelings for Chelsea; and Alan, Charlie and Herb take Judith to the hospital when she goes into labour.