Awwww! *hug* Tylenol and ice cream is a great combo. Cold pudding if the ice cream is too cold. Nice liquid or squishy foods like soup or applesauce or pasta can also help-- you don't necessarily want to chomp on apples and carrots the day you've been tightened. You may want to talk about good foods to eat that day or the next day-- can't always have a non-crunchy choice at school.
I got my full braces on my birthday, the summer before 6th grade. (I'd had headgear and an expander for a year before that-- that's another whole circle of hell by itself!) I got them partially off in December of my senior year, after having jaw surgery the previous June. I think they actually came all the way off a month before I went to college. Dunno what class it was, but it was an underbite. Ick.
Best of luck to your whole family, and I hope he doesn't ever have to have jaw surgery.
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