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Originally Posted by Lisa1970 
Does he have OCD?
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I don't know. When I think of OCD, and this may be off-base, I think of someone who has trouble functioning because of the need for order & cleanliness (or religious ritual or whatever their particular compulsion). I don't think he's that bad, but I don't have any real experience with it.
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Originally Posted by cparkly 
My mom is a wonderful mother. She is very, very creative. With that creativity came a lot of "stuff"; supplies, etc...She is a wonderful cook, but not a neat cook. Our home was very loving. It was also very disorganized. That really bothered me.
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Originally Posted by Smokering 
We had a large family, most of us crafted (so the house was always COVERED in bits of fabric, thread, paper, glitter, scissors and glue...), we homeschooled (which tends to breed "stuff" - books, projects, stationery), and none of us were really "into" cleaning. Mum occasionally instituted plans for cleaning schedules, but they always fells through.
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These descriptions both sound like our house.

I'm a writer, and I also do hobby art. We're always organizing some event or another, so there are usually piles of paper and "project" messes everywhere. We do try to keep the bathroom & kitchen cleaned daily, but we just have lots of little bits of "stuff" lying around.
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Originally Posted by Smokering 
So: is your house older/not as minimalist-looking as DS's friend's houses or whatever? Does he go to a kindy/school with very neat storage boxes and a clean-up time every day?
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He absolutely loved preschool. It surprised me because he's pretty intense, and I'd worried about him. One of the reasons was the shelves with a little box for everything. He was very impressed with that! And he liked that his teacher did the same thing everyday. Even the few times he got moved to yellow light for doing something, he said, "I broke a rule. That's what happens" in an almost Zen way like it somehow made him comfortable that rule breaking = yellow light, no matter what. We definitely are *not* like that, and I don't know that I could achieve that level of consistency.
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Originally Posted by Smokering 
Could this be his way of asking for his own room? If he has his own room already, could you fix it up with a new coat of paint and some primary-coloured storage boxes, or something?
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He does share a room with his sister, who is a little like Linus. If something can be made into a mess, she finds the way to do it! We have a downstairs den that is unused. DH asked him tonight if he thought converting that to his bedroom would work, but he said "no, it's too messy down there." (Since it's unused, it's becoming a dumping ground/storage area. Yeah, now that I'm writing all of this out, maybe our house is that bad.)
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Originally Posted by GuildJenn 
I'm wondering if he's worked alongside you or others and has picked up on all this, or if it seems to come out of nowhere.
For the wanting a different house bit, I'm not sure it means deep unhappiness (but you would have a better read on it of course). I think it is something kids go through at certain stages when they are classifying the world outside the home with peers and things. I'm not sure I'd've questioned him too much...it's good to know, but it also might be a good time to help him remember the things he does like.
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Sunday is our cleaning day, and let me tell you, he hops out of bed quickly. Seriously, he's a bit of a dictator about cleaning day, but I definitely don't wipe baseboards and those things. That's all him - because he "saw some dirt."
He's been saying these things for a while, which is why I questioned him. Over the past 2 weeks or so, they've become more frequent. He spent last week at my ILs house, and MIL is much cleaner/more structured/organized than I am. We got back late Sunday night, and this week, it's been an almost constant stream of chatter about the house.
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Originally Posted by lilmom 
I would say he definitely needs at least one part of the house that he can keep as neat and organized as he likes. It's probably just part of his personality and he will always be this way. I don't think it means he is seriously unhappy, but it probably genuinely bothers him and he probably WILL be very happy to have his own place one day. I totally get it. BTDT.
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In reading through everyone's responses, I'm thinking that maybe 1) our house does need major work and 2) he needs his "space." He doesn't have that. He sometimes goes to his room and shuts his door, but he does not have any space that is sacred for him.
-- In talking about this more with DH tonight, I thought of a few issues that probably are affecting our lives. First, I'm a bit of a hoarder. It's something I'm working really, really hard on, and we've been trying to go through everything. We're in the middle of a major purge right now, but I know that I tend to save, save, save. It drives DH a little batty, but he copes.
When I was growing up, I was responsible for younger cousins (we all lived with my grandparents) and then my sister from the age of 5 onward. By age 7, I was in charge of 3 younger cousins most days. By 9, I was in charge of cleaning, laundry, etc. Some of my laziness with housework now probably is a rebellion against taking on adult responsibilities as a child.
One of the reasons what DS said got my attention is that I recall vividly thinking, "I want to be an adult because then I can make my own decisions" as a child. I had a turbulent, abusive childhood, and I craved being able to decide for myself what would happen. I want DC to LOVE their childhood time and not spend it, like I did, waiting until they can get out & be happy.