Hey Julie, I just wanted to give you a
I wrote this whole long reply and then I just deleted it because I am no expert, having just been through it with my first and it was rocky. All I know is it seems very emotional and difficult for some kids, especially little boys. I think your gentle approach is best. I just couldn't not reply at all...
Hang in there! You're not a failure and neither is your little guy. He just needs time.
We used bummis pull up training underwear. It will hold more than ordinary underwear but he can still get wet clothing in them sometimes (depending). Then I would say to him "oh, you're wet. Let's go put your dry clothes on." Then he would undress and put his wet clothes in the hamper etc, so he was still very involved in dealing with his body processes.
You probably have tried this but having a quiet chat with him about it, asking questions etc can really help.

Hang in there! You're not a failure and neither is your little guy. He just needs time.
We used bummis pull up training underwear. It will hold more than ordinary underwear but he can still get wet clothing in them sometimes (depending). Then I would say to him "oh, you're wet. Let's go put your dry clothes on." Then he would undress and put his wet clothes in the hamper etc, so he was still very involved in dealing with his body processes.
You probably have tried this but having a quiet chat with him about it, asking questions etc can really help.
