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After old Sunny was gone, I sat in the chair for a while and smoked a couple of cigarettes. It was getting daylight outside. Boy, I felt miserable. I felt so depressed, you can't imagine. What I did, I started talking, sort of out loud, to Allie. I do that sometimes when I get very depressed. I keep telling him to go home and get his bike and meet me in front of Bobby Fallon's house. Bobby Fallon used to live quite near us in Maine. […] We thought we could shoot something without BB guns. Anyway, Allie heard us talking about it, and he wanted to go, and I wouldn't let him. I told him he was a child. So once in a while now, when I get very depressed, I keep saying to him, "Okay. Go home and get your bike and meet me in front of Bobby's house. Hurry up." […] I keep thinking about it, anyway, when I get very depressed. (14.1)
Holden tries to combat his depression by altering past actions, which is… doomed to failure. He needs to take some proactive steps, but he’s too far gone to even know what to do.
All the two of them were eating for breakfast was toast and coffee. That depressed me. I hate it if I'm eating bacon and eggs or something and somebody else is only eating toast and coffee. (15.17)
Holden feels guilty about bring privileged. His family clearly has money (he bounces between expensive boarding schools, his father is a "corporation lawyer," he has nice suitcases from Mark Cross, etc.), and it bothers him that not everyone has the same advantages—especially the nuns, who he later comments never get to go to "swanky lunches." Poor little rich boy.
After they left, I started getting sorry that I'd only given them ten bucks for their collection. But the thing was, I'd made that date to go to the matinee with old Sally Hayes, and I needed to keep some dough for the tickets and stuff. I was sorry anyway, though. Goddam money. It always ends up making you blue as hell. (15.32)
Money depresses Holden because it creates interpersonal barriers for him. Since isolation is what makes him feel sad, anything that prevents him from connecting to other people—like money—is going to be depressing. (Just try not having it, Holden, and then see how you feel.)