“She struck her bag right out in the middle of the aisle, where the conductor and everybody could trip over it.”

The first women Holden encounters is the mother of “the biggest bastard that ever went to Pencey, in the whole crumby history of the school.” Once he learns this I think he kind of freaks out as she is no longer just any random stranger. That’s why he thinks he can’t open up to her, because he probably feels that if he were to say anything personal Ernest would hear about it. So he doesn't ever say anything honest. He takes it very extreme, though, to the point where he feels the need to introduces himself as Rudolf Schmidt, which is interesting as it is Pencey’s janitor’s name. He even lies about having a brain tumor!! Who the heck lies about that?? For his own entertainment (and possibly to distract him from his sadness and loneliness) he starts “shooting the old crap.”

“He adapts himself very well to things. He really does. I mean he really knows how to adapt himself.”

Holden repeats the word adapt, of all adjectives, a lot when talking about Ernest. It’s the strangest word to use to describe someone. Mrs. Morrow doesn't seem to notice that Holden is just saying the same thing over and over again about her son. 

“Her favorite is The 39 Steps she knows the whole goddam movie by heart, because I've taken her to see it about ten times.”

He talks very highly about his ten year old sister Phoebe. She is described in a very positive note which makes her very likable. Holden mentions various little things about her such as the fact that she always writes stories but never finishes them. Endings are what make a story a story, ya know? From the way Holden describes her I doubt it’s due to laziness. Then for someone who thinks very lowly of movies and actors he sure has seen this movie a lot. (The meaning of The 39 Steps is never revealed in the movie).

But this is different from the other chapters Phoebe has been brought up as he finally mentions the flaw in Phoebe. He says she is too affectionate and very emotional. Which is weird because emotional support is exactly what he is looking for throughout these chapters.  

“There were these group of girls around thirty or so. The whole three of them were pretty ugly, and they all had on the kind of hats that you knew they didn't really live in New York, but one of them, the blond one, wasn't too bad.”

The whole time Holden is annoyed as each time he tries to talk to them but the girls could care less. They seem to just be using him to get some free drinks and giggling a lot (probably at him for trying to act older). He dances with them but just doesn't enjoy it, blaming it on the girl. He thinks she’s a moron yet he kisses her. Yeah, she gets mad but they keep dancing.

Once he again he messes with them too (perhaps because he feels like they have spoiled/wasted his night) by saying the actor Gary Cooper was on the other side of the room. They all fall for it and one even claims she saw Gary leave. He enjoys that. Then he got more annoyed with the girls when they told him they had to leave as they were going to get up early to see the first show at radio city. It depressed him and he said he would've bought them a hundred drinks if they hadn't told him that.

In chapter 13 Holden orders a prostitute. He keeps insisting it is just because he wants to practice for when he gets married, degrading her as if she only has the same purpose as the sports ball you would practice with to get better at the particular sport. This also shows signs of insecurity. Being the curious rich boy he is, he wants to ask her all about how she came to be a prostitute. He wonders how the store workers probably thought she was an ordinary girl buying a dress unaware of what she actually dedicated her nights to.  Anyway, once the prostitute, Sunny, takes off her dress, Holden quickly gets uncomfortable. He knows others would be turned on by this but not him. He can’t seem to really explain why. He just says, “I certainly felt peculiar when she did that… Sexy was the last thing I was feeling. I felt much more depressed than sexy.” He keeps repeating he feels peculiar. He was especially uncomfortable when Sunny rests her head on his lap. He just sits there and can’t move nor bring himself to ask her to move.He literally jumps at the first opportunity to put space between the two of them (putting away the dress so it doesn't wrinkle). He just wants to talk to the young girl. Then later he says the reason he doesn't want to do anything with Sunny is because she is so depressing. He especially judges her because she goes to the movies during her free (even though he has seen the same movie at least ten times). Then he says he is tired and just had an operation(again with those kinds of lies). It’s clear he is nervous.

Overall, lots of excuses.  

Each encounter isn’t that different from the last. With all of them, he is very intent on acting older than he is. He invites Mrs. Morrow for a drink but it’s close so he can’t and Mrs. Morrow doesn't think he is old enough to buy them. He tries (again) to buy an alcoholic beverage at the club and, despite insisting he looks older, he can’t buy one as he looks awfully young to the bartender. With Phoebe, he kept making it seem as Phoebe was too young to be able to get into the conversations between Allie and him.

With Sunny, though, we see this different side of Holden where he not only gets punched again but he also kind of wants to open up to her but Sunny is quick to reject that idea (however, she is a prostitute and she was woken up and forced to come to Holden’s room so, understandable). 

So more than anything he's so lonely. You see that when he is trying to call someone, he begins to list off people he could potentially call but doesn't end up calling anyone. Plus the list is so short and is quick to go through why he can’t call them. He really doesn't seem to have any friends. The only personal relationships he currently has are with people he is/was related to. He doesn't talk to Jane or Sally on a daily basis (though they do go to different schools) nor has he seen them in a long time. Basically he has no one so he looks to these women, almost, for help but none of them can help him as Holden is still running away from his problems and into new problems.

He is constantly looking for something to do, somewhere he can go but then complains when he is somewhere different. He is always walking or riding a cab to go somewhere but then he ends up back at his hotel room. He doesn't have anywhere to go  and he has no one. These encounters merely depict just how much Holden really wants someone to talk to but it’s always something. The lady on the train is not only thirty years older than but also Holden’s classmate’s mother. The girls at the club are not interested in talking nor does Holden depict them as being capable of having a conversation. It's funny how he orders a prostitute and then just wants to talk. He also (kinda) looks for comfort in the strangest places on the train, in the club, and in a prostitute.