In chapter eight, we find Holden on his way to the train station, folding down the flaps on his red cap to keep his ears from getting cold. Holden likes to ride trains at night. When the mother of one of one of his classmates (Ernest Morrow) gets on the train in Trenton, she spots the Pensey sticker on Holden's suitcase and engages him in the conversation. They are sitting on the train together, and Holden shows us the love of lying he told us about in a previous chapter. He tells Mrs. Morrow that his name is "Rudolf Schmidt", which is the name of the janitor at Pensey. Mrs. Morrow is quite attractive, and Holden begins to like her and he regrets telling her his name was Rudolf Schmidt. Mrs. Morrow and Holden have completely different impressions of her son, Ernest. Holden tells us, "Her son was doubtless the biggest bastard in the whole crumby history of the school. He was always going down the corridor, after he'd had a shower, snapping his soggy old wet towel at people's asses. That's exactly the kind of guy he was." Mrs. Warren describes her son this way: "He's a very sensitive boy. He's really never been a terribly good mixer with other boys. Perhaps he takes things a little more seriously that he should at his age." Holden then tells us, "Sensitive. That killed me. That guy Morrow was about as sensitive as a goddam toilet seat." Holden feels such affection and attraction towards Mrs. Morrow that he wants to make her feel good about her son. His impulsive barrage of fabrications regarding the wonderful character of her son comes tumbling out of him, born of his sexual attraction to Ernie's mom. When Mrs. Morrow asks Holden why he is going home a few days early for Winter Break, he makes up another outrageous lie. He tells her he has a "tiny little tumor on the brain" and needs to go in for surgery. When she invites him to come visit her son, Ernest, in Massachusetts sometime in the summer, he declines saying he will be traveling with his grandmother to South America. Holden gets a kick out of this lie because in reality, his grandmother barely leaves the house. He does not feel bad about this particular lie because "I wouldn't visit that sonuvabitch Morrow for all the dough in the world, even if I was desperate."

When Holden arrives at Penn Station in New York City, he decides to call someone to let them know he is in town. He spends about twenty minutes in a phone booth trying to decide who to call. He runs through a list of people in his head but comes up with reasons why he cannot call any of them. He thinks of calling his brother D.B., his sister, Phoebe, Jane's mother, and a few more friends, but in the end he decides it is too risky. Holden worries that word may get back to his parents that he has left school early, and he wants to delay telling them the bad news that he got kicked out of school.

Holden takes a cab to the Edmont Hotel. Holden gives the taxi driver his parents address by mistake. After they drive for a while, Holden realizes he forgot to tell him to go to the Edmont Hotel. Holden asks the taxi driver about his major concern; where do the ducks in Central Park go in the winter? The driver cannot give a satisfactory answer, but Holden invites him to have a drink with him at the Edmont nonetheless. The cabbie declines the invitation.

Holden is slightly concerned about checking into a hotel. He tells us "I'd put on my red hunting cap when I was in the cab, just for the hell of it, but I took it off before I checked in. I didn't want to look like a screwball or something."

The Edmont is a seedy hotel at best, and there are all sorts of strange characters staying at the hotel. When Holden looks out his window, he sees more rooms in the hotel. The guests do not even bother to pull the blinds, so Holden is getting quite a show. Holden watches a man getting dressed up as a woman, and in another room he sees a man and a woman spitting some liquid at each other. Holden tells us the hotel is full of perverts. This bizarre sex play makes Holden excited, however, and he starts to think about his sex life. He admits to us that "sex is something I really don't understand too hot." Though Holden has fooled around with girls before, it left him feeling "crumby". He says, "In my mind, I'm probably the biggest sex maniac you ever saw." He starts thinking that maybe he will call "Old Jane" but then remembers they do not like it in dormitories when you call late at night. Naturally, this causes Holden to create a story explaining why he is calling at such a late hour. The story involves the sudden death of Jane's uncle. But Holden decides not to call her because he has lost the mood. Next, Holden remembers a guy from Princeton gave him a phone number of a girl in New York, named Faith Cavendish. Faith is not a prostitute but is known to enjoy casual sex. Holden calls her, even though it is very late. She is quite angry at getting a call so late at night and the fact that she does not know him or remember his friend, but she begins to warm up as the call continues. Holden deepens his voice, so he sounds older and asks her to join him for a cocktail that very night, she declines but offers to meet him the next day. Holden says he cannot meet her the next day because he is just in town for the night. Of course, he immediately regrets the fact that he turned her down as soon as he gets off the phone. Holden does not know what he wants. He wants sex, but then he doesn't want to have casual sex. He says, "I think if you don't really like a girl, you shouldn't horse around with her at all, and if you do like her, then your supposed to like her face" and he goes on to say, "if you like her face, you shouldn't be wanting to spit water all over it."

Chapter 8 and 9 take us from Holden's train trip to New York, where he meets Mrs. Morrow, a classmate's mother, to the beginning of his stay at the Edmont Hotel. In these two chapters, we are given a first-hand example of Holden's tendency to lie and we get to know more about Holden's personal feelings about sex. Holden is confused about sex because he wants to have sex but does not want to have sex with someone who he does not like. But then again, if he cares about a girl he doesn't want to do anything "crumby" with her because he does not want to degrade her in any way.