Alan and Jake meet Walden Schmidt, a broken-hearted billionaire.

Jake is taught the art of infidelity by Charlie, whose girlfriend is away for Christmas.

When Chelsea convinces Charlie to let Alan’s new girlfriend, Melissa, move in, the girls end up taking over Charlie’s house.

Charlie must make a difficult decision about his future and with which woman he wants to spend his life: Chelsea or Mia.

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…

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

Charlie’s desperate to make sure Chelsea and Evelyn don’t befriend each other following their first meeting.

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…

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

Charlie’s admission that he’s in love with Chelsea gets a surprising reaction from her

Charlie has to remove a half-naked woman from his bedroom before Chelsea arrives.

Charlie ends up in couples counseling.

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…

After getting unusually turned down at a bar, Charlie learns that a website has been made dedicated to exposing his lifestyle. Charlie sets out to find who created the site,…

After Charlie’s night with a girl is ruined due to Alan’s interruption, Alan moves in, being kicked out of his house by his “suffocated” wife: Judith. The next day Alan…