There’s something about a skinny brunette wearing clunky black shoes. I liked Jenny’s shoes. I told her so as we sat on the front steps of the therapeutic day school for at-risk students we worked at in Chicago’s Lincoln Park neighborhood.

We were on a break and playing that game where you each pick out someone and ask the other” “Would you sleep with him/her?”

Any girl Jenny picked that looked like her was always a yes. And being we were near the campus of DePaul University, there were a lot. Shoulder-length curly black hair, pale face, slim not-so-athletic body and imperfect nose. And clunky black shoes.

I liked Jenny’s shoes. When Jenny and I went back inside we met the person who loved her feet. Well, not just Jenny’s feet. Any feet. It didn’t matter if you were a female or male staff member. Michael would dive at their feet and embrace them like he was bowing down to a king. Sometimes he would weep.

There was obviously something wrong with Michael, but then that’s why he was here. All the kids here were messed up in one way or another. At least Michael wasn’t one of the violent ones, or one of those who would shit on the bathroom wall. When he went to the time out room he would stand in the corner, do his time and return to class peacefully. Others the staff would have to share turns restraining for what could be up to two hours.

We had one kid, Roderick, who was always scratching his ass. I finally asked him one day:

“Roderick, why are you always scratching back there?”

“Because it’s dry in here,” he said.

Most of these kids you really felt sorry for. Shitty home lives, shitty health, shitty dispositions. For most of them we were their real family. There were a lot of struggles, but a lot more success stories. But some of my favorite stories are from when the kids were gone for the day and the staff went out to play. Especially the Friday before Jenny’s last Monday before she quit to focus on grad school.

We found an empty couch at a crowded bar on Lincoln Avenue. She laid across the couch with her clunky black shoes on my lap. We decided to play the “Sleep With” game one last time.

“Would you sleep with her?” she said, pointing to a bookish brunette with over-sized glasses and Doc Marten boots. “Yea, I think so,” I replied.

“Ok, she said. “Would you sleep with me?”

“Yea, I think so.”

“Time to go then,” she said.

It was the first time I saw her apartment. The first time I saw her bare feet (not bad – maybe Michael’s on to something) and the last time I saw Jenny.