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James - the difference would seem to be that you had MANY friends, whom your parents probably knew, and apparently it never crossed the line from friendship into romance. That's good. Intellectual maturity is not the same thing as emotional or sexual maturity. No one would have a problem with a 40 year old coach mentoring a star athelete - but marrying her is a different ball of wax. I'm not much on 14 - 16 year olds getting married, even to each other. Can it work? Yes. Is it likely? No.
A normal 40 year old man should not be looking to young girls for romantic relationships. Hey, at least let them get out of high school!
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