
In The Catcher in the Rye Holden Caulfield gets kicked out of his fancy prep school, Pencey Prep, and goes back home earlier than expected. He attempted to hire a hooker in the hotel he was staying in, but ended up too nervous to have sex with her, and ended up getting roughed up and paying more money than he actually owed for it, which certainly didn’t help his mental frame. He spends a few days in NYC being lonely, failing to connect to everyone, and slowly goes mad, culminating in him ranting and raving to Sally Hayes, a girl he asked on a date, who becomes upset and leaves. This was one of the major breaking points before he decided to head out west and live as a recluse. His sister tries to come with him, but he refuses and instead takes her to the carousel, which cheers him up immensely. He seems to be in a mental institution in the epilogue due to his mental breakdown.