This meme is referring to when Holden receives an offer from the elevator man to have a prostitute to his hotel room for five dollars, which Holden accepts. After the prostitute leaves, without anything happening, and Holden pays her the five dollars, the prostitute and the elevator man claim the amount was ten dollars (which it was not) and they steal the money from him.

This meme is referring to Holden's date with Sally Hayes, where Holden unloads to her about everything he hates about school, and asks her to run away with him. Sally refuses, which makes Holden upset, calling her a “royal pain in the ass” (Salinger 133).