Hi, I am a mother of 3 children and found that children tend to grow up a little and want to stay up with mommy & daddy. I say this because this is what I always went through at bed time. I recommend being as supportive as possible. Taking this time to find out what is soothing. Soothing can be done in many of ways, you can create a room environment that is soothing, making bed time relaxing and sleepy. Sounds of nature, a symphony lullabye or a teddy bear that sings a lullabye, has a heartbeat or even reads a soft bedtime story. I also suggest maybe getting him involved when he is awake and finding out what would make him feel better about bed time. I used to lay with my kids until they fell asleep because I knew thats what my children needed, considering bedtime seemed very unhappy to them. (I always used the night time for me time and I feel that my children often wondered why do I have to be sleeping when mommy is still up). Not knowing then or understanding how confusing that is for a child, thinking I am the adult and didn't have to goto bed withought me time, probably caused more problems for bedtime in my home. But I didn't just lay around and relax either, kids are a part of the atmosphere, its almost like being left out.( I'd have the music on, or be cleaning, organizing or even had friends over). No one likes to feel left out. I am not saying you shouldn't enjoy being an adult and having me time, but perhaps keeping a relaxed zone or even keeping it behind the scenes is best. I can say I got to a point to where it was frustrating and I decided my children needed to go to bed on there own, but if they was upset I would lay with them to make them feel better. I didn't have the good ideas that are out there available to me as easy as they are made to be today. I wish I did. Although nap and bedtime was much easier and nicer with the soothing sounds of the ocean and nature. Maybe even a video projector with a lullabye could help. I really feel at times children tend to go through the I am missing something stage and that could be all it is, but making him feel protected and loved is most important. Great job mom! I know it seems tedious and time consuming, but letting your children know how much you love them and taking the time to understand, deal with and adjust to there insecurities, uncomfortableness and irritability and to help soothe them means more to them than we probably could ever know. Good luck, I wish you the best in overcoming this problem and I hope your son gets some peace with bedtime and can rest well and easy.