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Dear Sierra:
I think it is not worth pursuing, so if I was you, I wouldn’t. Your obsessing about him, looking for clues, mind reading, that is wasted energy and using your words, it drives you crazy. So better stop it.
The reason I think it is not worth pursuing is because he wasn’t too shy to ask you questions when he tutored you, you answered pleasantly, it was a friendly exchange and he had plenty of opportunities since to talk with you again, and so, I don’t think that the assumption that he is too shy to approach you is a reasonable explanation to why he hasn’t.
If you find out that you are unable to let go, then approach him at a time when he is alone and ask him what you want to ask him, so to bring the issue to a close, so you no longer wonder.
anita