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We started slowly this week with school and my son is doing great with the spelling words. I am just reviewing and he is getting them all right. I had decided to do the words because I thought he could not spell them but he can when I ask. That's where is stops though. He will NOT try to spell anything outside of that. He asks me everything even to the point of texting for me in the car today and I said tell her, on my way. He stressed and said you will have to tell me how to spell. I said NO you know how just figure it out. He did and it was fine but he won't try.
So my question is how do I get him to try? Should I do the dictation? Would that help him to see them more in a real life context> OH btw he is 9.

First I would tell him with anything that he has to write it first, and then you will look at it and correct it if needed. Make sure he knows it is ok if you have to correct it. It sounds like he is afraid of getting it wrong. Is he a perfectionist in other areas? If he knows you won't help him then hopefully he will stop asking. You might want to try dictation also to get him used to writing sentences without any help. Maybe knowing you aren't allowed to help with dictation will also keep him from asking and he will gain more confidence.