FWIW DS is similar and also a very similar age, April bday. For a bit he did seem to need me to just be a bit stern and tell him enough was enough. Some nights he cried and some nights he got up and I put him back and some nights he rolled over and went to sleep. It seemed more about him testing to see what mommy would do if.....he just didn't want to go to bed b/c he wanted to do something else and had grand ideas of his own! But the more consistent I was the less and less he pushed. He still tries a bit and is irrational about it all, so having conversations don't really work. I just had to tell him that if he got up, I would put him back and if he got up again, I would put him back and if he got up again, I would put him back, because it was time for sleep. It seemed to help for me to basically spell it out for him ahead of time. The one time he got up but didn't leave his room, so I didn't go in and just left him to it, ended up being how he learned he could play and go to sleep when he felt tired...so long as he did not leave his room.
So, essentially his biggest issue is not settling enough to actually get into bed unless you argue and he starts crying? And it sounds like he is trying to do physical things to get himself worked up and then cries afterward once you've had a fight and he does eventually lay down then? I am also wondering if he needs some kind of physical release last thing in the day. I wonder if you can give him a children's exercise type thing to follow that he can do in his room or yoga or something where he is ALLOWED to do something physical before bed, but in a productive way that is more allowable than whatever it is that he is doing himself?
Mine are very spirited/physical and before bed they love to run, play, jump, dance, fight, wrestle. I feel like it's making them more alert and less drowsy and it BUGS me, but it does seem like they NEED to do that some nights. I wonder if you gave them a timer and let them do that stuff for a certain amount of time and then gave them something calming to do afterward if that could lend itself to a better routine for what they need? Maybe 20 mins of roughhousing a bit with each other, THEN teeth, pajamas, music, dim lights, etc. Mine tend to want to do the rough stuff right after bath and it's a battle to get them into pajamas even. Once the pajamas come on and we brush teeth it's like we turn the corner and start calming down a bit more. Then DD does her quiet play, I do stories lying in bed with DS, then switch and do stories lying in bed with DD. If you don't like the idea of letting them do whatever they want, you could maybe try to give structure to it and ask who can do the most push-ups or who can jump the highest jumps, and try to change the activities from more active to more calm as you go? Some big muscle stuff at first, then some yoga stuff toward the end? Who can breathe the quietest? Who can hold this pose the longest?
Just tossing out thoughts as they come.
