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This is really difficult. I have a 5 year old, 3 year old and nearly 2 year old and juggling bedtimes is one of the most frustrating things we deal with. Most of the time, my wife and I divide and conquer, but when one of us is home alone, we try to put them down in shifts. My 3 year old needs someone in the room with her to fall asleep, so we try to put down the 2 year old and move on from there. Often times, she comes into our room in the middle of the night and we just let it happen, Some of those times, we will wait until she is asleep and carry her into her bed. Keep trying different things until you find what works. Good luck!
You may want to try some new tricks to get him to stay in his bed. I put a baby gate up on my 3 year old's doorway to encourage him to stay in his room. Then I put a fish tank in his room with lights so he could watch the fish. Finally, I put a CD of bedtime stories on in his room. It is a kids CD of classic stories like Peter Rabbit and Thumbelina. He listens to this and falls asleep.
Now this will only work if he is tired. SO you have to look at his nap schedule. Is he napping too much or too long in the day? If so, try limiting his nap or letting him cut it out all together. Also, make sure he is not hyping up as the night approaches. If he is running all over the house it will be hard to put him down to sleep.
Lastly, make a chart with stickers. When he goes to sleep well...and stays asleep..put a sticker on his chart. If you stay consistent, it will work. Just don't give in and sleep with him or he will learn just to cry or get up longer. Good luck!
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