Go about it gently & lovingly.
If he's already mentioned that he would like to get them fixed himself, then chances are he's already come across some not very nice people who've already judged him because of it. He's probably feeling low about himself.
Is he easy to talk to? If you think he would be receptive, I would definately grab his hand, and ease into it. Or if he mentions his teeth sometimes, then wait until the next time he brings it up, & then tell him.
I think it's wonderful that you look past the outer shell of someone. He is lucky to have you. As you've already said, that not everybody is as deep as they should be.
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