How has J.D. Salinger made New York both familiar and strange in The Catcher in the Rye? What is so ironic about this juxtaposition?

Holden Caulfield has grown up in New York City. Throughout The Catcher in the Rye he points out memories from his childhood about different locations. Because of this, it would be safe to assume that Holden should know his way around the city pretty well. It would be ironic if he ever felt lost because even though New York City is a big town, anyone who calls it his home town should be more familiar with it. By having Holden feel both familiar and strange in his home town, Salinger may be showing how the boy's mental capacities are waning. We also get a look into how Holden can become confused and unreliable as a narrator because of the mental distress he is suffering.

One example of Holden becoming confused and lost in New York City is when he forgets the fencing team's foils on the subway. The following is his explanation of the mistake:

"It wasn't my fault. I had to keep getting up to look at this map, so we'd know where to get off" (3).

Granted, New York City is big and the subway system is probably the most complex in the world, but a native might have been able to handle finding the right stop. On the other hand, this can prove that even natives don't always know the city like they think they do. This certainly sets Holden up to discover more strange parts of the city when he becomes a runaway.

For an example, Holden gets a dose of the strange when he checks into the Edmont Hotel on the first night that he runs away. His perception is interesting:

". . . I checked in. . . I'd put on my red hunting cap when I was in the cab, just for the hell of it, but I took it off before I checked in. I didn't want to look like a screwball or something. Which is really ironic. I didn't know then that the goddam hotel was full of perverts and morons. Screwballs all over the place" (61).

It's as if Holden is discovering a different side of New York City that he never knew existed; however, one would think that his parents would have taught him about certain areas to avoid. This begs the question if Holden was specifically trying to experience a different side of New York, or if he was simply naïve. Either way, the answer would be ironic because the unexpected seems to happen to Holden at every turn. Just when he thinks he knows how to handle a situation or place in New York City, it turns out differently than he expects and that is a good example of irony.