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Update
So the mom and I couldn't connect last night as she fell asleep so I wrote her a letter with my concerns. She received the email and wrote me back very committed to making this work. She came this morning to do the school drop off and she saw how her youngest is and is on board for coming up with a plan. It is clear though that she is more of a negotiator than I e.g talk with him for 5 mins about the importance of mittens then another 10 mins about his options (I am more- let's figure this out then if it's still not working you get strapped in the stroller and go). I explained how this isn't possible all the time as I've got to get one kid to school and have 3 others standing around in snow suits. He is definitely difficult but as I've said all along, workable. The mom agrees that the drop off's don't seem to be working as he needs more time to settle into the program before heading out (which is what I've been saying). So we'll see.
Oh and she failed to mention that she and the boys just moved out 2 wks ago on their own. I learned that from the 3 yo. She had told me about the seperation but had said a yr a go.
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Wow...newly separated parents, a new home and a new daycare all at once. No wonder the poor kid is throwing fits! I have to say this may be tough for you. That is a lot of change all at once and the kid is probably wondering what hit him. He probably misses his dad, and his mom if he has been home with her until now...that is a whole lot for a kid that age to adjust to! Poor kids! I hope you are able to work things out with them, but don't feel bad if you can't...that is a lot to take on!
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I agree with sunnydays this is a lot to take on...that kid is definitely going through a LOT! But hopefully you can make it work...I once had a difficult child, similar to the one you have, and I remember actually liking the challenge...it is SO rewarding to have a child like that, then work with him and to have the child make a complete 360. However given his family situation who knows how things will turn out...good luck!
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Since this little one is reeling from all the changes in his life, he needs someone loving, kind and firm with him. Routine is really important and I wouldn't negotiate to much with him. He needs to be shown who is in charge (again gentle firmness) and what needs to be done to get him to school successfully. Too much change in such a short period of time. He really wants direction and to know what to expect.
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I am with Mimi success for this child is going to mean absolutely no negotiating - cutting him some slack now and again yes but your way that's it. Clear instructions and clear results for obeying or disobeying as the case may be and then 100% followthrough. It should only take a few days for him to grasp the way things are going to be and you might be surprised to find he is happier for it and behaves.
Mom needs to be careful that she is not being too lenient in a mistaken belief that she needs to make it up to the child somehow.
Child is old enough to talk to in the sense of saying things like I get that you are angry, I get that you are sad but that does not mean you can show your anger by not listening to me and doing as you are told....etc.