Had to laugh tonight. Boy child (9) not going to bed! Finally he melts down and divulges problems of the day while cuddling the current husband. He's sobbing 'I've had a really bad day, 5 really bad things have happened to me today. The 1st is that I have to go to bed now, the 2nd is that I couldn't find a pen in the whole of the house because I wanted to draw. The third is that I banged my head at swimming because so and so pushed me. The 4th is that so and so was calling me names so I called him gay and then the 5th is that the teacher didn't see any of this and threatened to call my parents into the school - aarrrgggh it so not fair'. Went into nice comforting mum mode without laughing! Does it get easier?
Some kids are just naturally pre-disposed to be night thinkers and worriers. It may/may not go with being afraid of the dark or being alone too. He seems to be worrying about a mixture of trivial and more complex things . Could you introduce a period, pre-bedtime when you talk about the day in full - with the premise that bed is for sleeping not thinking? Sounds like a lovely, sensitive young man.
My ds is 11 and is a night thinker. The easiest way is to let him talk it all out and even then he can go on for what seems like ever! I've found the best thing is to have a set time when he has to stay in his room and then at least even if hes awake I can still sleep! Hes also got a notebook he can jot all his thoughts in and we'll talk about any 'big' things in the morning.