The Drew Carey Show (1995)

S8E10 Drew's Girl Friday

Drew is thrown into a frenzy when his coworker departs, worried that his superiors will uncover his lack of skills. To boost his technical abilities, he enlists the help of a savvy teenager. On another front, Steve takes up residence with Lewis and Oswald, but his incessant sobbing and overly emotional outbursts about his failing marriage soon wear on their nerves.