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While I understand your point, the attitude about the money seems a little.... off.
I would consider other punishments, and not taking his college money. It seems ineffective as a punishment.
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Totally disagree. Braces are not "required" in the same way as getting cavities filled. Despite everything, braces are purely cosmetic and discretionary and were certainly done with the assumption that only once would be necessary to pay for a permanent solution.
To OP, if your son has any source of income at all, for any week he skips his retainer even once, you confiscate a week of his salary. I don't know how you'd do this exactly but you have to make clear on a very real basis that this cost a lot of money ane he WILL pay you back for any value he is "stealing" from you. And plan on him wanting to quit his job just out of anger so come up with a contingency if he cuts off his nose to spite his face.
He doesn't have to believe it is fair but I would guess he will see it that way at least by the time he is out of college.
Who wanted the braces? Many kids don’t really care it’s the parent who wants the kid to have the braces. If mom pushed the braces and the kid d cared less it’s more on her for pushing the kid d into something he didn’t want. It was cosmetic. Another poster suggested when the kid was older if his teeth bothered him he would have to pay for it. A bit like a kid taking years of piano cuz parents wanted him to and now, years later the kid doesn’t play. Parenting isn’t about how much money you “wasted” on your child. Perhaps this lesson is more for the parent
Clearly, you need to make him wear the retainer every night, or his teeth will shift back. It's the same concept as making them brush their teeth. You wouldn't tell a 2 year old that you won't send him to college if he doesn't brush his teeth.
Have a discussion with him, in which you make him understand that he needs to wear the retainer for at least two years, and probably until he leaves for college, maybe longer, or the teeth will shift back. Have him set an alarm on his phone to remind him to put in the retainer. If the retainer isn't in, he loses his phone the next day.
Do you give him money? Turn it into a payment for wearing the retainer. If you gave him a weekly allowance of say $20/week, turn it into paying him $3 each morning for having worn the retainer the previous night. If you didn't already give him spending money, start doing so by paying him some amount each morning for having worn the retainer.
Once the habit is established, he's more likely to keep doing it, and give you less grief about it. You can help him establish that habit through a system of immediate rewards and punishments.
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