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Funny, when I first joined here like over 4 years ago now, Indigo was way cool. Everyone was talking about Indigo for a boy, and I didn't get it and thought it seemed girly because it was a color. I've come a long way with names since then, and think it's perfectly masculine, and its similarity to Inigo helps a lot, too.

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Indigo (the color) makes me think of a warm night in an exotic place. It's very adventurous, and the Inigo [Montoya :P] association helps that too. So I'd pair it with other globe-trotting, adventurous things, like Indigo D'Artagnan, Indigo Porfirio, Indigo Quatermaine, or Indigo Sacheverell. Yeah.