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When I read the subject heading I thought "no", but to be honest you're kind of selling me on it lol! I'm not a fan of the name Sky on either gender but I always figured it was better on a girl. Now, I'm actually liking it a lot more on a boy. Not just because of your cowboy analogy, but now I'm thinking of it as sort of a handsome/cool name in general.

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Sky Thomas sounds cool and has a nice flow. That one's my favourite for sure.