We just finished 3 months of something similar. He was teething (getting all 4 molars and 4 canines in at the same time). Even with some ibuprofen it still hurt, and he started to really hate going to bed because he knew the night would be unpleasant... poor kid would start to cry when he realized it's time for bed. Thankfully, it got A LOT better once the teeth finished moving in.
Have the ped check him out to see if there is any cause for pain (ears, teeth, etc.) And just try to keep comforting him as much as you can when he wakes up crying. If you all think it's psychological, it might be fears... has anything changed in the room? Does he seem scared of anything? Good luck!
at 11:13 PM on Jun. 3, 2011