I have a six-year-old who has woken up every night for his entire life at 3 a.m., crying saying that he is scared. He already has a night light and sleeps in the room next door.
Many children go through stages where they do not want to sleep alone, fuss at bedtime, wake up at the same time, but go back to sleep when given support by a parent. Teach them that the parent is there for them and loves them but that they have to learn to fall asleep again. Boundries should be set in a firm and friendly or loving manner.
The stage is normal, but in your case, I don't think this is a stage - since you point out it's been happening for a long time.
Your son says he is scared, so I assume he has a sense of apprehension about something that may still happen. Talk to him about what he is scared about and see if you see patterns such as monsters or thieves.
Praise him when he has an occasional good night. Tell him that you are proud of him if he makes some progress - even if it is slow progress over time.
During the day, focus on ways to help him gain self-confidence. Be very careful, given his temperament, when he is exposed to television - look for cues as to what might be causing his anxiety.
The fact that you mention this happens every night and for his entire life tells me there is an unresolved issue - which may ultimately need the wisdom of a psychologist.
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