I usually try not to make these things personal, but "Not Pretty Enough" was ruined for me by a badly-sequenced mixtape from a man who turned out to be kind of a douche.
I'd never heard this song until it an online "friend" threw it on a mix for me during a holiday CD exchange. Due to circumstances I'd rather not go into, I interpreted as "See how enlightened and understanding I am of the female condition." I'm pretty sure I'm not the only woman who was "gifted"this song.
Minus the history, the song itself is fine, but even under the best circumstances, it makes me cringe slightly. Yes I know this is due to a lot of internalized misogyny and archaic ideas about how an adult woman is supposed to sing, but the childlike voice plus the pleading lyrics, "Am I not pretty enough?" makes me more than a little uncomfortable. I welcome vulnerability, but why does women's vulnerabily always have to be expressed through insecurity?
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