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Eh, I like Jacob despite it being so popular right now. Judith is out-dated.

Yes

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Both Jacob and Judith are nice names - lately I've been really liking Judith. And if the names were chosen because parents truly liked them, not because they start with the same initial, I couldn't see anything wrong with them.

ok, but nothing special

yes

I don't like either names but i don't like them as sibset.
how about Jacob & Julia?

Nope

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I really dislike matchy twin sets - in your case, it's the double J name that is a turn off.

Not bad, but

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I don't like the matchy first letters. Also, I don't necessarily think the style is the same, even though they are both Biblical names.