Who's the Boss? (1984)

S5E15 First Date

Feeling disheartened that Angela resorted to hiring an escort for a dinner function, Mona persuades Tony to take Angela out on an actual date. However, their outing feels less like a first date as they realize their deep familiarity with one another. The situation takes a turn for the worse when Angela uncovers the true motive behind the evening, leading her to confront a rude stand-up comedian in a fit of rage.