Ep 17. Jonathan Plays Cupid

Jonathan Bower, Angela's son, is at it again on Who's the Boss? season 2 episode 17. In "Jonathan Plays Cupid," the young matchmaker sets his sights on his mother's boss, advertising executive Simon. Jonathan decides that Simon and Angela would make the perfect couple, and he sets out to make it happen.

Jonathan's plan involves getting Simon and Angela alone on Valentine's Day, and he orchestrates it with skill. Angela, however, is not too thrilled about the situation and tries to talk Jonathan out of it. She tells him that it's not appropriate for her to date her boss, and that she is not interested in Simon in that way.

Jonathan, however, is undeterred, and he keeps trying to make his plan work. He manages to get Simon to agree to come over to their house for dinner on Valentine's Day, and he sets up the perfect romantic atmosphere. He even makes sure that Simon brings flowers for Angela.

As the evening progresses, Jonathan watches as his plan begins to unfold. Simon and Angela seem to be getting on well, and Jonathan starts to think that his matchmaking skills have paid off. However, things soon take a turn for the worse.

As the night goes on, Simon becomes increasingly jealous of Tony, Angela's housekeeper and the father figure in Jonathan's life. Simon sees the close bond between Tony and Jonathan, and he starts to feel left out. Things come to a head when Simon accidentally spills red wine on Tony's white shirt, and a heated argument ensues.

Angela is left feeling embarrassed and upset, and she realizes that Jonathan's plan was not such a good idea after all. She tells him that he should not try to force people to be together, and that he should let things happen naturally.

The episode ends with Angela and Simon agreeing to keep their relationship professional, and Jonathan learning an important lesson about meddling in other people's lives.

Overall, "Jonathan Plays Cupid" is a lighthearted and entertaining episode of Who's the Boss? It explores some interesting themes around family, relationships and love, and does so in a way that is fun and engaging. As always, the performances are strong, and the writing is top-notch. Whether you are a fan of the show or simply enjoy sitcoms in general, this is an episode that is well worth watching.