Oh C., I could have written your post myself!!
I have 3 boys, 2 have been potty trained since age 2.5. BOTH of my boys continue to do this, they are now 6 and 4. They wait until the last possible minute to use the potty and their undies are frequently "damp". They don't seem to care and it has been a constant cause of frustration for me!! I have talked to my doctor about it and he says it's perfect normal..in their little minds, in the time it takes to stop playing and go to the bathroom, a space ship will come down from the sky and bring candy and they will miss it because they were using the potty. This is how they think and why they hold it too long.
I don't know what else to say other than just keep after him and remind him to go often. It is hard not to make it a power struggle - I find this especially with my older son. I use positive rewards and I don't scold him or make him feel bad about it, I just encourge him to go right away when he feels the need to. GL!
C.
WAHM to Joe (6), Tyler (4) and Dylan (1)
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