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Tami, my husband is still like this and he's 42! My daughter is a lot like him. My Big DS, is to some extent and he knows, at 17, that this is not a good thing and it bothers him.
To some degree I think it is a personality thing, especially since my DD and DH are very much alike personality-wise.
She "lost" her iPod (gift from Grandpop) at her friend's house. It was missing for over a year before her friend found it. She has left countless sweatshirts at school, never to be found again. Her big brother is taking bets about how long it will take before she loses her cell phone. If she does, we won't be replacing it and SHE KNOWS THAT.
Her chore today is to clean out all the junk she left in the back of my van when we went away last weekend.
I'd stop giving him lunchboxes and just make him carry a brown bag. If that means he doesn't get to have a COLD drink, well, too bad. If he can prove that he is able to be responsible in other ways, then give him back the lunchbox.
Part of the problem is that once the kids hit middle-school age, the teachers do less of that structured reminder thing that the kids come to depend on. At the end of the day, the teacher is not telling the children to pack their homework, bring home their lunchbox, put on their coat and hat.
Maybe you could put a laminated "checklist" on a keyring that is attached to his backpack but kept in a pocket. He can check the list before packing to go home. Jacket, lunchbox, homework, planner. He can use the same list in the morning to get ready.
I make it a policy not to "rescue" my children by going back to school for what they forget. I also won't bring things to school if they forgot it in the morning--with the exception of lunch for my younger kids, because there is no provision for that at school.
When my DS was in about 5th grade and really bad about forgetting stuff, if he didn't bring home his planner every day he forfeited his computer-game time for that day. That made a big difference with him.
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