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The first time I actually saw Skyler for a boy, that's how it was spelled. So that's the most natural choice for me. For some reason, perhaps because the few female Skylar's I know are spelled with the a instead of the e (and one tryndee SkiLar, no joke), it seems more masculine. I have tried to like Schuyler, but it just doesn't feel right to me, if that makes sense. I just gravitate towards Skyler - the same as Hailey is my preferred spelling as that's the first way I'd seen it spelled.

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I've never actually met a female Casey, although I have heard of a few, and most of them had more trendy spellings, like the ones you pointed out.

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I'm sure there are people that do that, and I wouldn't hesitate if he looks like a Skyler (and of course, Rob agrees). I just took a lot of flak from Rob's family about Casey being a girl's name and it never really dawned on me that someone else might not see the names I pick in the same light that I do.

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:)