My son — let’s call him B. — sat in his cubby on his first morning of kindergarten this year. He clutched his R2-D2 backpack while begging me to take him home. He had been excited about kindergarten until this very moment, but now he was crying.

“What’s wrong, buddy?”

“I’m feeling shy,” he choked out.

B. has been many things in his six years and two days, but “shy” is not one of them. Any kid in a Pokèmon T-shirt is immediately his friend. He offers high-fives to strangers in parking lots. Last year at this time he was leaping into his new preschool class, Crocs first. But kindergarten has made him inexplicably bashful.

Seeing him folded up in the cubby, I realized how tall he is. His body barely fit. At the same time, he hasn’t looked this small and vulnerable in a long time.

“Come on,” I suggested. “Let’s go to your table.”

The classroom was dark with soft music playing. The other kindergartners were sitting quietly (and, I noted, tearlessly) at their tables. I was the only parent in the room. I led B. to his seat and we played a few rounds of rock-paper-scissors. He finally seemed calm so I made for the door. But then he chased after me, asking for a hug.

“How about a high-five instead?” I suggested. I didn’t want him to cling.

“High-six,” he corrected me. He offered an open hand and an extra finger from the other hand. It’s a high-six because last year he was in High Five, the preschool program across the hall. Now he’s moved on and we have to add the extra finger. I gave him a high-six, told him to be good and to have fun, then turned and walked away briskly while he stood there sobbing. I’ve read a half-dozen “First Day of School” books to him, so I know this is pretty normal. He’ll cheer up after a few flips of the page, right?

No such luck. That night he told me he cried three times on his first day of kindergarten.

The second week was even worse. The moment we told B. to get ready to leave, he started begging us to let him stay home. One day he said he was sick, even though he was in a chirpy mood all morning (even putting away a waffle and a banana). He dawdled over socks and shoes and went to the bathroom three times. He asked if I could take the long way to school.

So I took winding routes through north Minneapolis and we played his favorite car game: We pick a category and go through the alphabet naming things for each letter. One day the category was “school” and I took it as a good sign that he could name many things he likes about kindergarten: C for coloring, N for the niceness of his teacher, P for the pigeon book she read yesterday, and T for the name of a preschool pal who’s in the same class.

But his shoulders slumped as we walked toward the classroom and, once again, he cried at the door. At this point I was no longer entering the room. I wanted these goodbyes to be easier.

And it’s not just the goodbyes that are hard. B.’s mother and I know that he cries two or three times a day. We found out he’s also getting “breaks” for acting out. This is all too familiar. B. was excused from more than one early childhood class due to his impulsivity. He shoved kids and threw things and used words no child should know. Our first attempt at preschool lasted only five days.

We sought help and things improved. But we’re still left to wonder — is this a setback or a spiral? Will B. adapt to kindergarten? Or will the days get more and more grueling for him? It feels like there’s too much on the line. It’s hard to escape the thought that his attitude about school will be shaped by his experiences this first year. And to some extent, so will the school’s attitude about B. I don’t want him labeled a “problem child,” with a reputation that turns into a self-fulfilling prophecy.

Then again, I don’t want him to feel bad for simply feeling bad.

On the last day of Week 2 I decided to stop telling B. to “be good.” I wouldn’t even tell him to “have fun.” After all, he can’t choose these things for himself. He’s simply swept away by emotions bigger than he is.

Here is what I told him instead: You are brave.

I reminded him of a joke that made him laugh a few days ago, and he flashed a timid smile. Meanwhile, I reminded myself that I can’t fix the situation with a few words.

“I wish I didn’t have to stay here all day,” he said morosely.

“Me, too,” I answered in all honesty.

I gave him a high-six and walked away.

Kurtis Scaletta is a writer in Minneapolis. He published this story with his son’s permission, though his son asked him not to use his full name.

ABOUT 10,000 TAKES: 10,000 Takes is a digital section featuring first-person essays about life in the North Star State. We publish narratives about love, family, work, community and culture in Minnesota.