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I would rather see Jack as a nickname for John than on its own, by personal preference. It doesn't seem to particularly lack spice/be boring. Here are some MN suggestions:

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Jack August
Jack Clemente
Jack Vincent
Jack Harold
Jack Henry
Jack Thomas
Jack Oliver
Jack Anders
Jack Francis
Jack Laurence
Jack Angus
Jack Ernest
Jack Horton
Jack Florian
Jack Lewis
Jack Timothy
Jack Simon
Jack Samuel
Jack Isidore
Jack Columba
Jack Ferdinand
Jack Benedick
Jack Sebastian
Jack Ashley
Jack Wilfred
Jack Frederick
Jack Alfred
Jack Archibald

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As to two middle names, I don't think it would be too much of a hassle. I don't particularly have a stance. Never minded a lot one way or the other. I tend to just use one in my combos.