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While I was changing my shirt, I damn near gave my kid sister Phoebe a buzz, though. I certainly felt like talking to her on the phone. Somebody with sense and all. But I couldn't take a chance on giving her a buzz, because she was only a little kid and she wouldn't have been up, let alone anywhere near the phone. I thought of maybe hanging up if my parents answered, but that wouldn't've worked, either. They'd know it was me. My mother always knows it's me. She's psychic. But I certainly wouldn't have minded shooting the crap with old Phoebe for a while. (10.2)
The one person he seems to feel closest to (and the one person he reaches out to) is his younger sister, Phoebe. Sure—but only because she hasn’t had a chance to disappoint him yet. Just wait until she hits puberty, Holds.
But there was one nice thing. This family that you could tell just came out of some church were walking right in front of me – a father, a mother, and a little kid about six years old. They looked sort of poor. […] The kid was swell. […] He was making out like he was walking a very straight line, the way kids do, and the whole time he kept singing and humming. […] It made me feel better. It made me feel not so depressed anymore. (16.3)
Sometimes, just observing is enough to give Holden a sense of connection; watching the little boy makes him "not so depressed anymore." Careful: it’s a slippery slope to a restraining order.
When I finally got down off the radiator and went out to the hat-check room, I was crying and all. I don't know why, but I was. I guess it was because I was feeling so damn depressed and lonesome. Then, when I went out to the checkroom […] the hat-check girl was very nice. […] I sort of tried to make a date with her. […] She said she was old enough to be my mother and all. (20.37)
Holden keeps tying together the words "depressed" and "lonesome," suggesting that being lonely makes him depressed. Notice how, once again, he tries to reach out to anyone around him, including the hat-check girl, as he earlier did with the cab drivers? But it’s a catch-22, because his depression ends up pushing people away. How … depressing.