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I like Gwendolyn. I like Gwendolen even more, because the -lyn part seems dated to me, and makes me think of -lyn endings on names like Jerilyn and Gracelyn. I don't think of it as classical, but it's heroic-ish and that's as good. Gwendolen seems crisp and friendly and, yeah, pretty but pretty like green leaves or shiny agates, rather than pretty like phlox or lace. I like Gwen more than Wendy - Wendy is childish to me. Gwen is youthful but not childish.

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I don't think Josephine goes with Gwendolyn at all. That might be part of why the sister set didn't poll well - it's a clash. Gwendolen is an originally feminine hero-name and slightly "exotic" due to the Welsh Gw-. Josephine is just a really common male Biblical name with a feminizing ending qualifying it, super conservative and somewhat prissy IMHO.

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- mirfak