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I looooooooooooooove Ashley on a boy. It bores me to tears on a girl, but I think it's so handsome for a boy. I do tend to like a lot of softer male names: Gabriel, Tristan, etc.

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I would worry about how it would be received in the 'real world' though. I bet most people don't know it was originally a boy name. Don't let that stop you from using it if you really love it though. If people can name their daughters Ryan and James you can name your son Ashley.

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I'd definitely pick a very strong, obviously masculine name for a middle name.