Who's the Boss? (1984)

S2E17 Jonathan Plays Cupid

After a conversation with a concerned friend, Jonathan begins to fret that Tony might eventually drift away from him. To prevent that from happening, he sets up a special Valentine's Day dinner for Tony and Angela at a cozy restaurant, aiming to spark a romance. However, both Tony and Angela mistakenly believe that the mysterious benefactor, "Mr. Bower," is actually Michael, Angela's former husband, leading to a series of misunderstandings that complicate Jonathan's well-intentioned plan.