Here is another thing to think about.
Does he relate bed time to punishment?
Time outs should never be in his room or bed.
I could never stress this enough to parents...
Bed time should never be thought of as a punishment in their subconscious.
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I agree with Amy, don't make the potty trip fun, it is not social. He is afraid of missing out on some socialization...
Have a get ready time, and a bed time. The longer he takes to truly settle down in bed, the earlier his get ready time is.....all playing has to stop more than an hour before bed because he takes too long settling down. Get on pajamas, brush his teeth, say good night to everyone, go potty...lots of time on the potty...then, get into bed.
We had evening "quiet time" too. It was time that no toys were allowed out, books, or coloring only. No running or horseplay. It was a time we used to teach good indoor behavior too. If a video was to be watched, it was not allowed to be something that would encourage her to get up and jump around, no barney or fun and dancing. Indoor voices only, TV volume low, light turned down and walking the through the house is slow and quiet...as though you had a sleeping beast in the house. It was wind down time; it allowed the adrenal levels to drop in the body. So, lying her down in bed was not like taming a wild animal.
My daughter was afraid she was missing out on something fun being in bed.....so when she did call me in, I made a big deal because she was waking me up...I was just dozing off. Told her she doesn't like being woken up and she gets cranky...."do you like when mommy is cranky?".
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I would try quiet time and wind down time first. Maybe starting right after dinner....It is winter time and it gets dark fast. If the street lights are on then it is quiet time (then those nasty street lights are the bad guys...LOL). Then have a 'get ready for bed' time....with plenty of time to go potty.
If he asks to go, then you see he did NOT go, Scold him for fibbing.
When he asks to go again, he is to be scolded for not going before.
His actions aren't getting consequences...if you think about it you are not discouraging lying unless you scold him.
It would only take once for him to go, then claim he has to go again, and you sternly deny him the request. The worst case scenario is you wash his bedding in the morning.
If you are worried about regressing with potty training,
Give him a dose of his own medicine...He claims he has to go so much, he can do it on HIS time.
Do it to him when "HE" wants to do something...watch a video play with a new toy, or go for a treat......wait, go to the potty...go again, ...go again...
Then bring it up...that he always does that. He always has to keep going...And if he'd stop doing it, then you'd know he is a big boy and really knows when he has to go. After a while he may understand the "Boy who cried Wolf" principle.
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I never had to resort to a creative idea for making her realize the importance of bedtime. But I did give an idea to a mom in the past.
Her son was 4 and decided he wanted to be up all night. Just would NOT go to sleep. So, if he needed more awake time, he was denied naps....awake time is for the day, not night. Eventually it worked, he was exhausted at night and went to sleep, and the daytime naps were allowed again, but shortened to make sure he was not getting his days backwards.
GOOD LUCK