A self-loathing, alcoholic writer attempts to repair his damaged relationships with his daughter and her mother while combating sex addiction, a budding drug problem, and the seeming inability to avoid making bad decisions.
Hank saves Karen from embarrassment with a drunk Richard, then covers for Richard by pretending to be dating a stripper named Holly, who takes a liking to Tyler and offends his girlfriend, Becca. Meanwhile, when she's fired after an inappropriate encounter with Stu, nanny Lizzie calls on Charlie and allows their relationship to progress, only to have Marcy beg for her return.