The message about "huge difference in personality" is a bug. I have already reported it in the bugs forum, although there has been no official response.
Anyway, I have done some testing on tutoring, and I 've found that this message just means that the players started disliking each other, which is partially random. I have seen cases when both players have EXACTLY the same personality attributes (DET, Ambition etc) and still dislike each other, with a "different personality" message.
As for tutoring. The personality of the youngster may or may not change irrespective of whether tutoring is lated deemed as "successful" or not. According to the game, "successful tutoring" is when the players like each other at the end, not when the personality of the youngster changed to an improved version. This is clearly wrong, but that's how it currently is.
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