Caroline in the City (1995)

Season 4: Episode 13

Del and Caroline participate in the company's mentoring program, but Caroline's adolescent charge Stan develops an embarrassing crush on her, while Del's turns into a teenage fixer who takes over Del's professional and personal lives with impressive competence. Meanwhile, Reg tries to convince Richard to sell his art, but the results are disastrous: a coffee house show is a fiasco, and when Richard desperately tries to emulate a subway hawker and sell his works to consumers, he is busted by an undercover cop who confiscates his art.