The trouble with girls is, if they like a boy, no matter how big a bastard he is, they'll say he has an inferiority complex, and if they don't like him, no matter how nice a guy he is, or how big an inferiority complex he has, they'll say he's conceited.
Holden is remembering a time when Jane is out on a date with a guy named Al Pike, how Holden thinks is all muscles and no brain. He askes Jane why she would go out with a bastard like Pike and Jane says she feels sorry for him because he has an inferiority complex. He feels bad that a nice guy like Bob Robinson gets turned down instead.
I think Holden himself has an inferiority complex because of the way that he judges others, to make himself feel better. Holden can probably relates to Bob Robinsion; the nice guy who loses out. Its obvious he feels this way about himself because Holden makes his siblings sound like geniuses and he's the loser. Holden seems to talk about random things, but the main thing they have in common is how depressed the make him feel inside. Holden seems to have an inferiority complex because he feels sad when someone gives him gifts, like the time his mom gave him hockey skates.
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