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Naïve is both one of Chris's most-used insults, and his least favorite word. According to the Merriam-Webster English dictionary, the word "naïve" means "deficient in worldly wisdom or informed judgment; especially: credulous"; Chris, however, defines it in the July 10th Messages as merely "questioning one's intelligence", showing that he only understands the most overly simplified definition of the word. By the time of the Jackie e-mails, he had apparently corrected his definition outwardly, but unless he really cares about his non-existent experience, he probably still believes it simply means "stupid". In the Wallflower E-mails, he finally uses the correct definition, confirming that "naïve" is really just an unacceptable jab at his unwarranted self-importance. He also refers to it as "the cruelest of words". He often pairs it with "retard", "slow-in-the-mind", or one of his many other CWC-ism insults.

The origins of Chris's disdain for this word likely come from occasions when it has been used against him in attempts to give him constructive criticism, such as the Vivian Gee E-mails. He seems to have twisted its original, relatively polite meaning into the worst insult he can muster. When Kacey's father called him naïve during the Father Call, Chris became enraged, almost to the point of threatening physical violence – of course, he quickly backed down once he was reminded that he was giving threats to an ex-Marine.

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