“Trick or Treat”

Act One

Charles and Buddy enter the Pembroke living room. Buddy has a date with the classy Diana Marks tonight. Jason arrives. It's Halloween tonight, and Jason still doesn't have a costume. Buddy wants to get out of his date with Diana; he is worried that Diana will realize Buddy isn't as perfect as he seemed when they met, and Diana won't want to go out with him. Charles reveals that he gave up his date with Gwendolyn because Mr. Pembroke asked him to stay home and give out candy. Lila arrives home with a dilemma: Sally Stefanado is throwing her annual Halloween party, and Lila can't think of an original costume. Charles suggests that she goes as Prince, but Lila says everyone is going as Prince. Jason and his mother are arguing about his costume choice: a Ghostbuster ("He wants to go out with his friends and beat-up children in sheets!"). Douglas helps Lila think of a costume idea, and in return, Lila agrees to introduce him to women (when he's older).

During dinner, Mr. Pembroke tells Charles and Buddy about a girl he dated in college who was way out of his league (it was Mrs. Pembroke). Jason comes down for dinner dressed as Charles (though he says he's going as Frankenstein). Buddy wants Charles to drop his book in front of Diana (the same way he met Gwendolyn) so Charles can start a conversation with her and find out about her interests. Lila and Douglas arrive for dinner dressed as a washer and dryer; Douglas is coming along to the party to take notes on girls. Jason leaves for trick or treating, and Mr. Pembroke allows Charles to go out with Buddy. Mr. and Mrs. Pembroke secretly follow Jason.

At the student union, Charles drops his book in front of Diana, while unbeknownst to him, Gwendolyn watches.

Act Two

Buddy tries to explain to Gwendolyn, but she won't listen. Charles chats with Diana, who wants to make a good impression on her date. Charles asks who Diana's date is, and Charles reveals that he is best friends with Buddy. Diana wants to know all about Buddy to make sure that he will find her interesting. Meanwhile, Buddy tries to convince Gwendolyn that he has a date with Diana, but she doesn't believe him. Charles returns to Buddy and apologizes to Gwendolyn. Charles advises Buddy to stay away from Diana.

Charles and Buddy return to the Pembroke house so that Charles can hear about Jason's adventures. Lila and Douglas return from the party. Lila is happy to have an original costume, and Douglas has realized there is "something about" girls. Charles tells Buddy that he is Diana's fantasy, and Buddy has two choices: he can go on the date and be a disappointment, or give up one date and live forever in her mind. Jason returns home, upset that his parents followed him, but excited to show off his candy. Charles reconsiders his stance on Diana, since he has realized that Halloween night is magical. He and Buddy return to the student union to meet up with Diana and Gwendolyn.