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I see it as an older name, because my grandfather's name was Jay (he changed it from Jacob in his twenties). Recently, though, a good friend of mine by the name of Julian has started using Jay instead. Seems like everyone around him sees it as pretty dignified and retro-cool, and he loves it. I just see it as "grandpa." :P If Jane is great for a girl, Jay's not "too simple" for a boy! I like simple. Jay's nice in theory, but I probably wouldn't use it.