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Thats kind of what I did with Nathan at 30 months. I knew he could so I just didnt put him in diapers anymore. I did the naked method. It took him about 3 days to get the hang of it and by 7-9 was really good w/ peeing. Even in the tub/shower I had him pee in an empty shampoo bottle just to get him used to not "letting it fly". I found w/ my boys that either undies or pants but having both on was to much trouble to pull down. Now that its winter I would probably go w/ loose fitting sweats. It was about a week of not going anywhere I did make a few short trips but I put a pull up over his undies that way if he got wet he felt it. But only used pull ups at nap and nights. DS3 hated to sit to pee so we bought a Peter Potty and it worked like magic he would run in the bathroom pull it out and aim some people think its just a gimmick but it worked for us. I was determined not to stop once we started. He did have some issues w/ holding his poop but we worked through those ( he would wait until he went to sleep to poop for a few weeks). My ped suggested 2oz of prune juice a day to keep him soft and regular ( I mixed ours w/ apple juice and he thought it was a treat because I always cut his juice w/ water).
Good luck cold turkey worked here.
 
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