Hmmm. Maybe he is done needing that nap during the day. No. Maybe what I mean is maybe you could get him to sleep earlier in the evening if he didn't have a nap. Don't know if that is feasible for you or not. My daughter is three also, and dropped her nap quite a while ago - actually, it just got to be too much trouble to try to get her to go to sleep, so I dropped her nap! Anyhow, just recently her bedtime has become challenging again. So I feel your pain. We sit with her in her room til she falls asleep. Lately, it has been taking until 9:30 or 10 to get her asleep, even when she hasn't napped (sometimes we miss her "window" in which case she's "overtired" and totally wound). Tonight I told her I would stay with her only if she was laying still and quiet. When she wasn't, then I left the room. I only did this once, and she came out (I was sitting outside her door) and we talked about how I would come in her room as long as she was still and quiet, and she could choose to get back in her bed and be still for 5 minutes, and then I would come back in, or she could not and I would stay out. She got back in bed and was still and quiet and I sat in the hall, with the door open, and she went to sleep. I never even had to go back in the room. I have been reading little bits of the Sleep Lady book - sorry, I don't remember the title, but she is more into "gentle" methods, and gradually helping your child get to sleep alone. Maybe there would be something helpful for you there? I haven't read the whole thing, nor have I tried her "method" fully. And I'm a little leery of "methods" for getting kids to sleep, anyhow. But I thought I should at least answer your post since we seem to have similar issues! I hope you (we) find something that works!!!