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Roger has kind of a geeky image to me due to association, but it's not horrid... I don't know that it's ever been super popular in my circles (I've met very few of any age), so I'm not sure that it's one of those that will immediately feel dated. I would only consider Gilmour as a given name if it's honouring a family name. Otherwise, that's one that really shouldn't be imported into the world of given names.