L.C.
i think what you are doing is perfect. ask him, let him go when he wants to, but dont force him. dont worry about night time, my little girl is pushing 4 and just now is night time trained. its very common for a lot of kids not to be able to hold it through the night until they are 5 or 6. the more comfortable he gets with it, the better. if he hasnt fully done it on his own in a few months, then start buckling down a little more. it sounds like you are doing great! one thing that has always worked for me ( i have done LOTS of potty training!) is when he gets a hold of it a bit more, try putting on a pair of underwear under a diaper. that way he can feel the discomfort of the wet fabric, but you dont have the mess!