I have a 2 year old and naps are not a problem because 1) I do not allow her to drink anything with caffeine in it, ie teas and cola drinks. 2) She has a routine, meaning, when she gets fussy and I KNOW she needs a nap, I'll pick her up & take her to her room. I PLACE her in her crib and I will leave the room AND CLOSE THE DOOR. Because this is Mommy's routine, she usually winds down, closes her eyes & goes to sleep. However, I have let her cry it out & if she still crying after 15 minutes, I take some milk & I'll go back in her room and pick her up, give her some milk and rock her for about 5 minutes & put her back down. My point, SHE KNOWS SHE IS NOT GETTING OUT OF THE ROOM. This A-L-W-A-Y-S works for us. Take your son to his room- Close the door- Sit down & Rock him- then put him down- and leave the room, closing the door behind u. Let your son cry it out, if needed- but u are establishing a routine!