Who's the Boss? (1984)

Season 1: Episode 21

Tony fears he can't afford the ski club Samantha wants to join with her friends, but he lets her sign up anyway. When his attempt to economize by cleaning Angela's chimney himself fails, he must go back on his word and tell Samantha she cannot join. Refusing to borrow the money from Angela, Tony soon sells one of his prized possessions to be able to pay for Samantha's ski trip.