Thanks everyone for letting me know I'm not alone and all hope isn't lost for my son 
This morning before he left for school I asked him if he had cleaned up his room (his best friend was coming over tonight and spending the night to celebrate the end of the school year) and he gives me a cheery "sure did".
A couple hours after he left I walked in there to change the sheets on the bunk beds and I just couldn't believe what I saw. Clothes hanging out of the dresser drawers, clothes in his closet just dangling from hangers. To give him a little credit, last night his floor was covered with kinex and legos and this morning he threw them all in a big container and now just the container is in the middle of the floor. His dresser, desk and book shelves were all covered with all kinds of "crap" (that is my name for all the junk kids seem to be able to collect).
I just couldn't figure out how he thought his room was clean. I could tell he did do a couple of things, but when your room looks like a tornado went through it, picking up a couple of things does not make the room clean.
When he got home from school I took him up to his room and said "do you really think this looks clean" and he says "what" and I pointed at the dressers with stuff crammed in and hanging out and he said "well the stuff last night was just lying on the bed, at least I put it away where it goes".
I just shook my head and walked out. I probably should have used that as a teaching moment, but honestly, I was just so dumbfounded that he would think it was clean that I couldn't bring myself to have a calm conversation with him.
I usually don't argue too much about his room. It's his space and for the most part I let him be in charge of it. He is supposed to clean it once a week as part of his chores/allowance, but I don't get too picky about it being spotless. When he is having people spend the night though, I usually ask him to make it presentable so it looks like he takes some pride in his space (and so the friend doesn't break a leg when trying to walk through the room).
I've worked with him different times try and show him how to properly clean and organize his room, but it apparently doesn't sink in.
So I just hope someday he turns around, or at least finds a very understanding significant other.

This morning before he left for school I asked him if he had cleaned up his room (his best friend was coming over tonight and spending the night to celebrate the end of the school year) and he gives me a cheery "sure did".
A couple hours after he left I walked in there to change the sheets on the bunk beds and I just couldn't believe what I saw. Clothes hanging out of the dresser drawers, clothes in his closet just dangling from hangers. To give him a little credit, last night his floor was covered with kinex and legos and this morning he threw them all in a big container and now just the container is in the middle of the floor. His dresser, desk and book shelves were all covered with all kinds of "crap" (that is my name for all the junk kids seem to be able to collect).
I just couldn't figure out how he thought his room was clean. I could tell he did do a couple of things, but when your room looks like a tornado went through it, picking up a couple of things does not make the room clean.
When he got home from school I took him up to his room and said "do you really think this looks clean" and he says "what" and I pointed at the dressers with stuff crammed in and hanging out and he said "well the stuff last night was just lying on the bed, at least I put it away where it goes".
I just shook my head and walked out. I probably should have used that as a teaching moment, but honestly, I was just so dumbfounded that he would think it was clean that I couldn't bring myself to have a calm conversation with him.
I usually don't argue too much about his room. It's his space and for the most part I let him be in charge of it. He is supposed to clean it once a week as part of his chores/allowance, but I don't get too picky about it being spotless. When he is having people spend the night though, I usually ask him to make it presentable so it looks like he takes some pride in his space (and so the friend doesn't break a leg when trying to walk through the room).
I've worked with him different times try and show him how to properly clean and organize his room, but it apparently doesn't sink in.
So I just hope someday he turns around, or at least finds a very understanding significant other.