Holden Caulfield thinks about the nuns and his acquaintance with James Castle in response to his sister Phoebe’s demand that he name two things he really likes. She has accused him of not liking anything, and after he denies it, she insists, “You don’t like a million things. You don’t.”
Holden thinks of the nuns he met in a random encounter at the train station. The one who had a “nice smile” and a “helluva kind face” was an English teacher, and he ended up talking at length with her about Romeo and Juliet. Thinking they were probably doing charity work, he gave them ten dollars, even though they said they were not collecting money. Although he enjoyed talking with them, he was worried they would ask if he was Catholic. After they parted ways, he felt bad that he had not given them more money.
James and Holden’s brother Allie are two boys who died. His reflection that he hardly knew James, a fellow student at his former school, serves to distinguish him from the closeness that Holden felt with his brother. In Allie’s case, death came from cancer, but James took his own life by jumping from the dorm where they both lived. Holden thinks about all the bullying James endured and reflects on the coincidence that when he died, James was wearing Holden’s sweater, which he had lent him.
Although Holden had mentioned hanging out with his sister as something he liked, the two things he next thinks of are people he barely knew. The chance encounter with the nuns left him feeling guilty at not being able to help them more:
“Goddamn money. It always ends up making you blue as hell,” he had thought at the time.
In James’s case, it may be that Holden feels guilty for not helping him more when he was bullied. It is also telling of Holden’s deteriorating mental state that when asked to think of things he likes a lot, he thinks of two dead boys. When Phoebe calls him on this, he insists that he can still like someone who is dead.