Many people think about a situation so much that almost any solution can seem like the right one. In The Catcher in the Rye, Holden Caulfield's overanalyzation of events leads him to rationalize many of his own decisions. He rationalizes why he has not had had sex, why he ordered the prostitute, why Sally did not want to go with him, and why he only gave the nuns $10.
Detailing his own intimate opportunities, Holden considers why he has never had sex. Trying to explain why, Holden just comes up with excuses. "Something always happens...her parents always come home at the wrong time...there's always somebody's date in the front seat" (Salinger 92). By saying always, it appears as if he has been foiled every single time he has tried, by something out of his control. For Holden, this is one method of his rationalizations. Holden says that he has had many opportunities to "lose my virginity and all" (92) but never seems to quite finish the job.
Holden gives the impression of being inexperienced with girls, and thus does not know the right steps. "... she keeps telling you to stop. The trouble with me is, I stop. Most guys don't" (92). He is rationalizing why he has never had sex, through his many encounters with girls.
Once he returns to New York, Holden is unsure of himself after ordering a prostitute. Holden remembers a book he read at one of the schools that he has been to, specifically the suave and sexy guy that was in it, and realizes that he is definitely lacking in that department. He remembers trying to get a girl's bra off, and failing miserably. He desperately needs practice, saying "I wouldn't mind being pretty good at the stuff" (93). While waiting for...