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My image of the name Raven is too femme for a boy. As a male name it sounds like the name of a vamp character to me; over-the-top, about as far over as a girl named Logan. I guess because I've seen Raven used in a very mainstream way on girls/women, but never seen it on guys. Still it wouldn't be awful -- it would just be squicky to me at first. And as a middle name, pretty much whatever floats your boat.

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Trilby - sounds self-consciously fin de siècle, and such an unfortunate character to name someone after (probably only because she was supposed to be very beautiful anyway =P). I'm not approving, even though I know her generation won't even know what I'm talking about. Besides, now it's just a hat. A boy named Beckham - seems mediocre and predictable, but it'll probably fly just fine.