We've encountered this with DS9 over the past year or so. I noticed it more than anything else with things like clothes or toys. If we were shopping for him and I asked him to pick out a shirt or two, he had the hardest time and just couldn't/wouldn't make a decision. He would go back and forth and overthink things to the point that it would end horribly. Inevitably, DH and I would be so frustrated because it seemed such a simple thing to do, that our frustration and aggravation oozed and only exacerbated DSs frustration. DH has stated that he can no longer take DS shopping because he (DH) might develop an ulcer right there on the spot grin I'm a little better able to get DS thru these things.....

Anyway, my thought on this is that it's perfectionistic and DS is afraid to make the wrong choice and then not be happy with it later (unknowingly driven by me because I've told him that he has to wear what he picks out or play with what he gets, etc.). What I started doing is telling him that there is no "wrong" choice for things like this. If asked I offer my opinion or try to bring up issues that I know might give him pause at any time (ie. remember you didn't care for the collar on a previous shirt or didn't you have a car like this that broke once, etc.) I try to reinforce to him that he can make the decision and that if he just can't decide, either take some time to think about it and we'll come back or (in the case of clothes) turn it over to me and I'll decide. He's getting better at handling the frustration, or recognizing that it might cause him frustration and avoiding for the moment. <---- not sure how helpful that is in the long run eek

I mentioned it to the SW at school who thinks it is due to his 'need' to always be right, do everything well, etc. She did say that telling him, when appropriate, that there are no wrong answers and trying to help him thru the decision making process is helpful. It's kind of like when there are correct/incorrect answers, he has no problem deciding which, but when it's ambiguous he can't process it. Truthfully, I'm like this to a certain point also, so I get it.

Good luck. I know how frustrating it can be.