Holden Caulfield gets a lecture from his old teacher about why he is flunking, fights with his roommate, and decides he doesn't need to hang around his school anymore since he's gotten the ax anyway. He heads into the city to kick it for a couple of days.
Holden tries to get laid and fails. He desperately tries to get company – from out of town girls or from taxi drivers – but he remains lonely and alone. He does, however, set up a date with an ex named Sally; the date goes badly and Holden finds himself alone again. He has the chance to sleep with a prostitute who turns out to be a child, which depresses him badly. She wants ten dollars, even though the pimp (elevator man) told him it would be five. He gets beaten up by the pimp and they take his five dollars. This, too, depresses Holden badly, not because he lost money so much as the entire scenario.
Holden sneaks into his apartment to visit his little sister and hides in the closet when his parents come home. He seeks shelter with a former teacher, who is affectionate with Holden in a way that freaks him out. This, too, depresses Holden badly. He decides to light out, take off, go somewhere else. But first he has to say goodbye to Phoebe. When she tries to join him on his fool's errand, he decides not to go. It's one thing if his own innocence is ruined, but he's not about to be the cause of ruining hers. They go to the zoo and Phoebe rides the carousel a couple of times, while Holden contemplates her innocence. He returns home, goes to counseling, and leaves us guessing as to whether he'll do well in his next school or not.