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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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