My son went through the same thing about the same time, at two and a half. Have you tried asking your pediatrician? I finally did, and his wonderful pediatrician gave us a number of choices. According to our pediatrician, juices and raisins do not soft the stool. Only pears, peaches and plums will. Cut back on rice, apples and bananas. In any case, that didn't work for our son. We tried the Metamucil crackers plus a plethora of over-the-counter and one prescription supplements to soften his stool. Again, failing there. What finally worked was actually a mental process. Even though he knew instinctually, we went through the whole ingestion, digestion and excretion process, necessity, how it works on a two year old level. He knew we all did it. We asked him if he wanted to do it in his potty (the toddler one) or ours. He wanted our toilet, so we took him to pick out his own seat (the ones that goes on our normal toilet seat to make it smaller for them). And, in our house, my husband and I started to announce our #2 business, letting our son know how good it feels after, and almost making it into a fun game sort of thing, asking each other if it's time or compare when and well, I'll leave the rest to your imagination instead of totally grossing you out. I know. Not exactly class, but it worked. It took about a month, which is fast compared to all the other stuff we tried. The whole took about 6 months. Seemed forever. Our pediatrician said that every kid is different though this problem is common, the solutions are not. He did mention that for some, it's a psychological block, and as parents, we have to try to relax so they don't pick up on our stress over this issue. We took it a step further and made it fun. He's six now, and has not had any more pooping issues. Good luck.