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Definitely two meanings, and they really depend on the attitudes of the user, and what the user thinks is fake or real. So: A) "Pretentious" can be a useful phrase to describe something that is fake or pretend, or somebody who is [pretending] in order to conform. Sometimes it is still used that way. B) Its meaning has also become completely the opposite. In the English-speaking world, "pretentious" has become a catch-all phrase to criticize anything or anyone that is vaguely heartfelt, [intellectual], earnest, sincere, artistic, unconventional, [nonconformist], non-commercial, or not on TV, on Youtube or in the supermarket.
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