K.C.
Does he usually wake up dry? I would say to him "until you are dry for 2 weeks in a row", we aren't going to do it. Maybe make a sticker chart. 2 1/2 is very young to be dry consistently at night. Especially for a little boy. My son was in pull ups at night past 4 and still had the occassional accident after that. It is such a mess and so much work when it happens! It always seems to amount to 3 or 4 loads of laundry with the mattress pad and the various layers of bedding. My daughter was dry at night almost as soon as she was trained. They're all different. I'd definitely recommend a waterproof mattress pad if you're ready to try. I also know people who make their child go to the bathroom at 10 or 11 before they go to bed. If you're willing to do that, that may help a lot. Good luck!