22 episodesFirst aired 21 September 2009
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.
E1Sept 200921m
Charlie must make a difficult decision about his future and with which woman he wants to spend his life: Chelsea or Mia.
E2Sept 200920m
When Chelsea convinces Charlie to let Alan's new girlfriend, Melissa, move in, the girls end up taking over Charlie's house.
E3Oct 200919m
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.
E4Oct 200920m
Alan starts working for Evelyn as Charlie works to fix the relationship between Chelsea and Jake.
E5Oct 200921m
Jake stops at nothing to get away from Charlie and Alan, after they embarrass him out in public.
E6Nov 200920m
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.
E7Nov 200922m
Alan and Charlie are shocked when they wake up next to a strange woman, and try to find out what happened.
E8Nov 200920m
While overcoming a bad break-up, Chelsea invites her beautiful college roommate to stay at the house.
E9Nov 200921m
While Alan struggles to cure his baldness, Charlie deals with the problem that he can't satisfy Chelsea.
E10Dec 200920m
Chelsea wants Charlie to take dancing lessons for the wedding, when Charlie uncovers the truth that Chelsea has been lying about her finances.
E11Dec 200919m
Jake is taught the art of infidelity by Charlie, while Celeste is away for Christmas.
E12Jan 201022m
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.
E13Jan 201020m
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.
E14Feb 201021m
Charlie suspects Chelsea likes the lawyer representing Alan after his arrest for a bar fight.
E15Feb 201022m
Chelsea and Charlie's relationship is at risk when Charlie's jealousy comes between them.
E16Mar 201021m
Charlie runs off to Vegas and returns with a new wife, but she's not Chelsea.
E17Mar 201021m
Charlie and Chelsea have a post-breakup one-night stand.
E18Mar 201021m
Charlie has a return engagement with Chelsea's best friend, while Alan has an unexpected effect on a new female patient.
E19Apr 201018m
Alan is torn between the bad influence of Jake's new friend and the hotness of his mother.
E20May 201021m
Alan tries for an intimate night at a hotel with his new girlfriend, while Charlie takes a different approach to obtain the "girlfriend experience"
E21May 201021m
Charlie is visited by the ghosts of his ex-girlfriends while Alan and Jake are on a road trip.
E22May 201021m
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.
