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Cindy makes me cringe. The only time I have ever heard it is on that plastic doll that's one of Barbie's friends or something. So I guess that makes it seem plastic and false and painful to me. To me it's just like naming someone Barbie.

If it sounds "middle aged lady" to you, I guess it must have actually been used as a name for people where you are?

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Kyler IS pretty cool. It's definitely better than Kyle and I'd agree it sounds sleeker, somehow, than Skylar.
I do like Skylar too though ^_^ Even though people say it's horrible and trendy. I can't help it!