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I prefer the sound of Jessica, but I like Jennifer because I've known so many nice Jennifers. So many! To me the only "stigma" is from it being so common. I think it won't seem dated until after it has fallen completely out of use for a while - but even then I think it'll be an OK kind of dated, like Sharon or Julie, as opposed to an unappealing kind of dated, like Deborah or Doris.

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- mirfak