Dear Mrs. B,
I've written letters like this before. I wrote to Will's preschool teacher here, and I wrote to his Kindergarten teacher here. In both cases, I was writing about a boy they didn't know, entering a world he didn't know either. In this case, its not the same.
You were Will's Kindergarten teacher from spring break on. While the transition was tough, by the end of the year, he loved you even more than his first teacher. And when he heard that you would be his teacher again, he was thrilled... though slightly nervous that he's never going to remember your new name, since you were married this summer. So, if you hear some Miss S's instead of Mrs. B's, know that it will bother him way more than it bothers you!
So, you know Will and he knows you, and I think he is a lot less nervous this year. He knows the school and the routine. Its easier this year, than any before. Easier... for him. The problem for me is that he's still my baby, and you're still a stranger who will spend more time with him today than I will. You are molding him more than I am, and though you were his sculptor last year, I still have a hard time handing over the chisel, as I'm sure you can tell.
I laid in bed last night thinking about the first day of school. Thinking about all the decisions he will make that I will not be a part of, good and bad, and that he will look to you for approval, for healing his wounds, for guidance and wisdom. He will look to you for all the things he's used to looking at me for. You have my 4'3" 75 pound baby to shape for a year.... so I am writing this letter to ask you to do it carefully. Round out his edges, don't leave anything sharp. Make sure he is detailed and beautiful, strong and hard on the outside, but still slightly soft on the inside. Shape him well for me, because though he's six, he's still my baby. And when I sneak into his room to sleep next to him at night, I want my baby to still be there... even if he's taking up a much larger part of the bed.
Thanks and enjoy him!