The two sentences are a dead giveaway. The first is obviously being said tongue in cheek, since the second parenthetical phrase “trapped by social convention” denies the first, “Amanda is a free thinker”. The very definition of free thinker is one who uses their own reason to evaluate things, and is not trapped by social convention. Therefore, the second sentence is saying exactly what @Blueroses suggests and is a pun playing off of the LIFO saying that @ShaChris23 suggests with the link above. Amanda doesn’t even know when it’s not cool to be in until the first cool person jumps back out. Clever writing.
Maybe too clever for the author’s own good, since it left @ShaChris23 guessing at its meaning. Did you know that Ernest Hemingway rewrote the very last sentence of A Farewell to Arms 47 times before he was satisfied with it. What finally emerged was far simpler than many of the earlier versions.