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Waldo sounds dorky to me, but because of my age I don't consider my opinion to be in any way indicative of what names are up-and-coming among those who are in their child-bearing years. It's a common phenomena that grandparents are appalled by the names of their grandchildren, due to changing tastes.

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I do think of "Where's Waldo?" Objectively speaking, I don't see why Waldo can't fit in with Leo, Milo, and Arlo.