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Charlie’s romantic past catches up to him, Alan’s financial woes deepen, and Jake’s teenage years bring a new level of mischief and mayhem.
Charlie must make a difficult decision about his future and with which woman he wants to spend his life: Chelsea or Mia.
9/21/2009
When Chelsea convinces Charlie to let Alan's new girlfriend, Melissa, move in, the girls end up taking over Charlie's house.
9/28/2009
Alan ends up playing maid to Judith's new baby as well as his former mother-in-law. Meanwhile, Jake uses an incriminating photo to blackmail Charlie.
10/5/2009
Alan starts working for Evelyn as Charlie works to fix the relationship between Chelsea and Jake.
10/12/2009
Jake stops at nothing to get away from Charlie and Alan, after they embarrass him out in public.
10/19/2009
Alan's advice to Chelsea that she get breast-reduction surgery is not met with enthusiasm by Charlie, who kicks him out, but staying with Evelyn has its own challenges.
11/2/2009
Alan and Charlie are shocked when they wake up next to a strange woman, and try to find out what happened.
11/9/2009
While overcoming a bad break-up, Chelsea invites her beautiful college roommate to stay at the house.
11/16/2009
While Alan struggles to cure his baldness, Charlie deals with the problem that he can't satisfy Chelsea.
11/23/2009
Chelsea wants Charlie to take dancing lessons for the wedding, when Charlie uncovers the truth that Chelsea has been lying about her finances.
12/7/2009
Jake is taught the art of infidelity by Charlie, while Celeste is away for Christmas.
12/14/2009
Jake hopes to win back Celeste by writing her love songs. Alan and Herb hope to keep Judith from finding out they've become friends.
1/11/2010
Charlie opts to have a colonoscopy in order to avoid going on a trip with Chelsea to see her parents. However, when he returns home, he finds her parents at his house.
1/18/2010
Charlie suspects Chelsea likes the lawyer representing Alan after his arrest for a bar fight.
2/1/2010
Chelsea and Charlie's relationship is at risk when Charlie's jealousy comes between them.
2/8/2010
Charlie runs off to Vegas and returns with a new wife, but she's not Chelsea.
3/1/2010
Charlie and Chelsea have a post-breakup one-night stand.
3/8/2010
Charlie has a return engagement with Chelsea's best friend, while Alan has an unexpected effect on a new female patient.
3/22/2010
Alan is torn between the bad influence of Jake's new friend and the hotness of his mother.
4/12/2010
Alan tries for an intimate night at a hotel with his new girlfriend, while Charlie takes a different approach to obtain the "girlfriend experience"
5/10/2010
Charlie is visited by the ghosts of his ex-girlfriends while Alan and Jake are on a road trip.
5/17/2010
Charlie is miffed over Alan's planned attendance of Chelsea's birthday party and suffers the indignity of having Jake chauffer him around following a license suspension.
5/24/2010
