A.S.
The best advice that I can give is to start setting a regular schedule now. you need to gain control over his bed time. It sounds as though he is controlling the bedtime situation. you should create a set bedtime that is followed every night (obviously there will be nights that are out of the ordinary) and create a bedtime routine. We get into Pj's, brush teeth, read books, rub back and then I walk out -- tears or not. My almost three year old daughter knows the routine and she knows that if she gets out of bed, that I will come in and take one of her binkies away for the night. I have had to do it twice, many many months ago and she got the picture and has not gotten out of bed since. Your son could be waking up because he is overtired, which I know sounds odd, but is how it works with little ones. I highly recommend "Healthy Sleep Habits, Happy Child" by Marc Weissbluth. It has been my sleep "bible" since my daughter was three months old, and it goes up to the age of 5, I think. For my daughter, the later she goes to bed, the earlier she wakes up. So also, the earlier she goes to bed, the later she sleeps. I know it is hard to hear them cry, but you are doing him a favor by teaching him how to put himself to sleep in his own bed, without your assistance. If you stay calm and are consistent, it should not take more than two weeks to train him. Good luck!