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I have a similar situation. Liana is our top name, and I don't think it's going to change. I definately want my first daughter's middle name to be after my ggrandma Clara. But Liana Clara doesn't flow all that well. I haven't decided whether to just use Liana Clara or go with Liana Clare, even though my ggrandma never went by Clare.

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If I were you, I'd tend towards Charlotte Lynn because of the family connection. I'd also look around to see if there's a way to improve the flow though, if you wouldn't mind some tinkering. Maybe Charlotte Belinda, or Charlotte Rosalynn?

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I prefer the May spelling.