Tenn, does he have a comforter at all?

I am not really sure what to suggest. My 21mo falls asleep really easily, but he sucks his thumb and holds his sheet up to his cheek. Without that he probably wouldn't settle. My 3yo has good nights, and other nights we need to lie with him for a while until he's sleepy then we can leave (unless it's my DH who lies with him, he usually falls asleep before DS LOL!). I think there are some kids who will need help getting to sleep for quite a while, but they all eventually learn to fall asleep by themselves.

GL, I hope you find something that works.