So my 21 month old son has started not taking naps sometimes? This maybe happens once a week and has been going on for a month. I have a very consistent routine: he wakes at 7 and wind down at 12:30, in crib at 12:45 and he falls asleep by 1. But now, he just will not go to sleep sometimes. He is just talking to himself, singing in the crib. ?? Once or twice I have tried getting him out after about 45 minutes and letting him play for a little while, then trying the nap again. Today, it is 3:00 and he finally fell asleep. At what time should I wake him so that bedtime does not go to late? Should I be letting him fall asleep so late, or do I stop trying after a certain period of time?