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If these are my only two choices, I prefer Reilly. I can actually see how Rory is starting to look cute, even to me, but I had an alcoholic uncle named Rory when I was little (aunt divorced him), and I just have a negative connotation with that name.

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Reilly sounds younger to me, and less weird. I know when I was a kid Rory sounded really odd to me, and until very recently, it has always had that strange feeling to me; I think it would even if I hadn't known one in my life.