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The first thing is the younger party being protected and allowed to develop, which it sounds like she is.
For me the rough time comes from realizing that either your son is dating her for her age (legal I guess, but ick), or he has so much in common with a 16-year-old it's enough to carry a relationship, which... Dude, what did you do in those 13 years to not grow as a person, ick. I can definitely understand why it would change your perception.
Then again, there isn't really anything you can do about it, except express your disapproval every now and then, but make is easy for either party to end the relationship without an "I told you so". Of all the actions for you to not condone, this is pretty mild. He could have joined a cult, committed crime, or "date" a 12-year-old.
Why can people of different ages not have compatible personalities? Youre saying it like a fact but have you actually thought about it?
And comments like yours are the exact reason why he probably feels like he must protect his inner child against all odds. From what OP tells us, he has his professional life under control, so let him spend his free time however he wants. See my other comment for details.