Charles has been living with the Pembroke family at 10 Barrington Court for three months.
Charles and Buddy arrive at the Pembroke house. Charles has a date with Gwendolyn Pierce (Gwendolyn Pierce!) tonight. Lila arrives home and informs Charles that Alexander Morgan—the most excellent boy in the eighth grade—has asked her to help him with his homework tonight. Buddy thinks Charles should bring Gwendolyn back to the Pembroke house after dinner, but Charles doesn't think the children are ready. Mrs. Pembroke announces that the newspaper has assigned her to cover the opening of a new play, so Charles needs to stay home and watch the children that night. Buddy informs Mrs. Pembroke that Charles has a date, so Mrs. Pembroke suggests that Charles brings Gwendolyn over to their house. Charles calls Gwendolyn to cancel their date, but Gwendolyn agrees to spend a quiet night at home with Charles.
Later, in the kitchen, Charles talks to the children about Gwendolyn coming over and warns them not to bother her. Mr. and Mrs. Pembroke tell the children to be on their best behavior. Lila gushes over Alexander Morgan, and Mr. Pembroke tells Charles to keep an eye on Lila during her study date.
Douglas is playing a video game in the living room when Gwendolyn arrives. Charles kicks him out and greets Gwendolyn. Charles is nervous and tells Gwendolyn they are having Chinese food and that he speaks the language. Gwendolyn is impressed. Meanwhile, Jason is hiding in the closet. Alexander Morgan arrives for his study date with Lila. The delivery man arrives, and there is a misunderstanding about how many dishes Charles has ordered. Gwendolyn suggests Charles explains in Chinese. Lila comes downstairs and reveals that she has ordered the extra dishes and brings Alexander upstairs to study. Charles thinks Lila and Alexander should study downstairs. Douglas comes in and interrupts Charles and Gwendolyn's date.
Gwendolyn feels like she is being ignored by Charles because he is too concerned with the children. Lila warns Charles not to come upstairs or he will betray her confidence. Lila also reveals she has a tiny crush on Charles. Charles asks Jason, still in the closet, for advice. Gwendolyn meets Jason and reveals he reminds her of her little brother at home, and she feels homesick. Jason is being a nuisance, so Charles instructs him to spy on Lila and report back to him.
Upstairs, Alexander is working on algebra homework, but Lila has something else in mind.
Charles and Gwendolyn kiss on the couch. Suddenly, Gwendolyn pulls away and accuses Charles of "meaning" his kiss. Gwendolyn storms out. Douglas emerges to play his video game. Gwendolyn returns and tells Charles that all the guys she goes out with try to kiss her, but Charles seemed different, sincere. Charles does not like to be called sincere. He calls Gwendolyn "Gwendolyn Pierce, the beautiful" and "Gwendolyn Pierce, the superb". Gwendolyn says she's heard all about her as well, and she isn't sure she wants to be Gwendolyn Pierce. Jason reports that Alexander has said to Lila, "You know why I came here tonight".
Charles runs upstairs and barges into Lila's room. Alexander was only talking about homework, and Lila is disappointed in Charles for not trusting her and leaves. Alexander admits that he had no idea that Lila felt that way about him. Alexander is fed up with being "the most excellent boy in the eighth grade" because girls don't see him as a real person, just a contest.
Meanwhile, downstairs, Lila complains to Gwendolyn that Alexander actually wanted to do homework. Gwendolyn tells Lila she wishes boys would come over to only to do homework with her, because it would mean they respected her as a thinking person.
Charles and Alexander come downstairs, and Charles takes Gwendolyn into the kitchen. Charles admits he felt pressured all day because he viewed Gwendolyn as a name and not a person, but during their date, she was a person, not Gwendolyn Pierce. Charles kisses her.
In the living room, Alexander invites Lila out for ice cream. Charles, Gwendolyn, Jason, and Douglas come along just as Mr. and Mrs. Pembroke return home. Charles invites them to come along, but they stay home. They kiss when they realize there are no children in the house, and Mr. Pembroke admits having Charles has been a very good idea.