Preschool: the continuing saga

We are now in week three of preschool, but let us backtrack to week two. Last Tuesday morning, Silas told his dad that, and I quote "I'm just not interested in preschool." He told his teacher the same thing, several times. When I question him about this, he says that there are no interesting toys to play with there, but will also say that the school bus toys they have are his favorite. When I ask him what he likes to do there, he'll say "nothing" but when I ask him if he had fun doing art he'll say that art was fun. When I ask him if he liked his snack he will answer in the affirmative, and so on. He also talks about several of the kids in his class constantly and I have no clue how much of what he says is real and how much is made up, but at least he's showing an interest in the other children.

On the downside, the teacher mentioned that he seemed sad the whole time. That was a particularly rough day, as was Thursday. On Thursday, he cried at home before leaving for preschool, he cried all the way there, and he cried when being dropped off.

It's the anticipation that's the hardest for him to deal with. When all of this was brand new, he'd wake up and ask if he had to go to preschool that day. I'd say no, and then the subject was dropped. Now, he wants to know days in advance when he will have to go to school so that he can gauge how nervous he should be that day. And he asks over and over again.
Do I have to go to preschool tomorrow?
No.
Do I have to go to preschool after tomorrow (meaning the day after tomorrow).
No.
After that?
And so on. Last week on one of his school days, he woke us up at 4 am to tell us that he didn't want to go to preschool. He reiterated this statement countless times, our patience disintegrating with every repetition.

We have tried many different tactics to ease his separation anxiety. I knit him a little bracelet, which he keeps in his pocket so that it doesn't get lost. I told him that I knit all of my love for him into it and that if he keeps it close, my love will be with him as well. I've read him books about starting school, about dealing with separation anxiety, etc. We got him a little pocket picture album and printed pictures of everyone he cares about, so that he can keep that with him. We try to be very positive. I tell him daily that I think he's a smart, kind, and brave kid.

"Not so brave, " he'll say.
"Brave," I'll respond " because being brave means doing something, even if you're afraid to do it."

We encourage him to interact with the kids and the adults in the classroom. Despite his fears, he did select some shells from the beach last week and brought them in to show Teacher Debbie:
That was week two. We are now in week three: one day down, one to go. Today, and I say this with cautious optimism, was a bit better. He cried, but not so much. I had a long discussion with him about his day when I got home from work. We talked about what he did at preschool (painted a leaf, played outside, played train tracks, etc.) and then I asked him if he felt sad when his daddy left him there.
"Yes," he replied, "I felt sad. But then I felt better." I gave him a big hug and told him I was proud of him and how very brave he was. This time, he did not disagree.