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I dislike Henry and would never consider it. It comes across as weak and dithery. Harry as a nn is better, but not good enough. If I wanted Harry, I'd start with Harold, or probably Harald.

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Oliver is really, really appealing. Ollie isn't. So, I'd use Oliver happily enough as a mn only.

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So, John, nn Jack! I like it very much, it's a family name from way back, and though I don't mind John on its own at all - I really do like it - in today's world it's so uncommon compared to Jonathan (which I find wimpy) that I think a young John who went by John would spend a lot of time explaining. Jack is all nn in my head, but it's a nn I'd happily use and, if I were male, happily answer to. Jack, all the way!