What does your toddler eat during the day? 3 x meals, 2x snacks with plenty of carb/protein? Hunger could be a problem.
Maybe bub woke for one reason (hunger/pain etc) and then it because habit (it only takes a few days for a habit to form... But it can take weeks to break one).
My thoughts are that for a start he is having dinner too early, he could be hungry or perhaps his back molars are coming through causing him grief or perhaps he is having a growth spurt so is hungry.
Can you maybe cut down the day time nap? How long does he sleep for?
Try giving him supper before bed, things that will keep him full.
Banana & toast, weetbix or porridge
She wakes at 5:30am because she is hungry and she doesn't have any milk before bed.
She has woken a few times recently at 03:30 asking for blueberries but I just tell her she can't have any and she needs to go back to sleep.
Have you tried (as hard as it is) just repeatedly offering water? If he stops getting it, he might not keep asking?
How much milk do you give him? My DS eats dinner and then has about 240mls of 'growing up milk' before dinner and downs it even after dinner and banana and yogurt for dessert! May be that he just needs more rather than you having to stretch it out later.
He also goes through bouts of nightmares where he'll wake up crying.
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