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1. I don't think it sounds too pretentious. No more than like Victoria or Charlotte or Josephine. I think it sounds more old fashionedy cool. And it makes me think of Anne of Green Gables because she wanted to be named Cordelia. Although she probably got the name from Shakespeare.

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2. I don't associate it with Shakespeare because I've never read King Lear. I do love Shakespeare though. I'm guessing the character isn't a great namesake? I have his complete works, I should go read that.