When did the word 'nerd' evolve to mean cool?

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Being an avid fan of some of the challenging crossword puzzles in The New York Times, I occasionally even delve into the puzzle archives and attempt some of the ones from yesteryear.

Recently, I was working on a puzzle from Sept. 15, 1995, in which one of the clues was “teen outcast,” with its answer as “nerd.”

I sent an e-mail to New York Times crossword puzzle editor Will Shortz...