September 21, 2009 9:00 pm
Charlie must make a difficult decision about his future and with which woman he wants to spend his life: Chelsea or Mia.
September 28, 2009 9:00 pm
When Chelsea convinces Charlie to let Alan's new girlfriend, Melissa, move in, the girls end up taking over Charlie's house.
October 5, 2009 9:00 pm
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.
October 12, 2009 9:00 pm
Alan starts working for Evelyn as Charlie works to fix the relationship between Chelsea and Jake.
October 19, 2009 9:00 pm
Jake stops at nothing to get away from Charlie and Alan, after they embarrass him out in public.
November 2, 2009 9:00 pm
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.
November 9, 2009 9:00 pm
Alan and Charlie are shocked when they wake up next to a strange woman, and try to find out what happened.
November 16, 2009 9:00 pm
While overcoming a bad break-up, Chelsea invites her beautiful college roommate to stay at the house.
November 23, 2009 9:00 pm
Charlie discovers he has not been satisfying Chelsea; Alan attempts to cure his thinning hair without spending much money.
December 7, 2009 9:00 pm
Charlie discovers that Chelsea has not been completely honest about her finances.
December 15, 2009 9:00 pm
Jake is taught the art of infidelity by Charlie, whose girlfriend is away for Christmas.
January 11, 2010 9:00 pm
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.
January 18, 2010 9:00 pm
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.
February 1, 2010 9:00 pm
Charlie suspects Chelsea likes the lawyer representing Alan after his arrest for a bar fight.
February 8, 2010 9:00 pm
Chelsea and Charlie's relationship is at risk when Charlie's jealousy comes between them.
March 1, 2010 9:00 pm
Charlie runs off to Vegas and returns with a new wife, but she's not Chelsea.
March 8, 2010 9:00 pm
Charlie and Chelsea have a post-breakup one-night stand.
March 22, 2010 9:00 pm
Charlie has a return engagement with Chelsea's best friend, while Alan has an unexpected effect on a new female patient.
April 12, 2010 9:00 pm
Alan is torn between the bad influence of Jake's new friend and the hotness of his mother.
May 10, 2010 9:00 pm
Alan tries for an intimate night at a hotel with his new girlfriend, while Charlie takes a different approach to obtain the "girlfriend experience"
May 17, 2010 9:00 pm
Charlie is visited by the ghosts of his ex-girlfriends while Alan and Jake are on a road trip.
May 24, 2010 9:00 pm
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.