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I like Gilbert, but I've always seen it as as nerdy name as well. It's one of those names that I'd like to love, but I'm too afraid of naming my child that and then causing them to be locked in their own locker by all the Kadens, Bradens, Aidens, Jadyns, and Haydens they have to contend with throughout school.

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It also reminds me of Gilbert Grape. I like Gilbert Grape though.

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Combos....
Gilbert Augustus
Gilbert Nicholas
Gilbert Asher
Gilbert James
Gilbert Louis
Gilbert Jude
Gilbert Jasper
Gilbert Rylan
Gilbert Simeon
Gilbert Eben ♥

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I think it works better as a middle name.
Peter Gilbert
Miles Gilbert
Elijah Gilbert
Edward Gilbert
Ian Gilbert
Simon Gilbert
Martin Gilbert
Finn Gilbert
Thomas Gilbert
Josiah Gilbert

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Hipster?
Hipster covers a lot. You've got to be more specific.
Alex Gaskarth kind of hipster? No way; certainly not.
Vincent Perini kind of hipster? Well, alright, maybe so.