Years ago, fresh out of graduate school, I worked at a school in the suburbs and had an awesome boss. We’ll call her Diane. Diane was the principal at a predominantly white, predominantly Catholic private school. She was the only black person on the premises, and I was the only Jew, and I always felt like we had a special bond because of that (I am acutely aware that she likely did not feel the same).

Anyway, one day her 5-year-old son came to visit the school, and because we had this special bond (re: I was the only one standing there), Diane asked me to watch him in the yard while she made a quick phone call. He was a gorgeous little boy with huge, beautiful eyes and a vivacious spirit. As I was watching him, a coworker of mine came outside and sat next to me. She was a stuffy, judgmental old white lady who I had absolutely nothing in common with (other than our whiteness) and who, needless to say, never really “got” my sense of humor or personality in general.

It was clear she didn’t like me. But because I was young and insecure, and had a broad, all-encompassing respect for the older generation (a respect I now hand out more selectively, thanks in part to this woman but also thanks to the various old ladies who have spit at me on the streets of NYC), I still felt the need for her approval.

So I tried to strike up a benign, friendly conversation as we watched Diane’s kid climb the jungle gym. “He is just too much, isn’t he? Such a beautiful kid. Diane is in so much trouble when he gets older.”

The woman turned to me, completely unamused and said, “You know, it is subtle statements like that that keep racism alive and present. Most Caucasian people inherently just assume that African American children will grow up to be ‘trouble makers,’ and that attitude becomes a self-fulfilling prophecy for them. I don’t see why you would conclude, just from looking at an African American boy, that he will cause trouble when he’s older.”

I stared at her, stunned.

And in that moment, I decided I no longer gave a fuck what she thought of me. Yes, she was old enough to be my grandmother, but you know what? Grandmas are assholes, too.

The prospect of no longer having to impress her was altogether freeing.

“I think you misunderstood me. I said ‘Diane is going to be in trouble when he’s older,’ because he is gorgeous and girls will be falling all over him. Which was a joke. But, to be clear, a joke that had nothing to do with race, and zero to do with him making any actual ‘trouble.’ The fact that you would jump to that conclusion makes you, in fact, the subtle, underlying racist.”

Watching this stuffy old white woman’s face crumble was one of the most satisfying moments of my life.

A few days later, she removed the Swastika-adorned wigwams that had been decorating the entryway to her 2nd grade classroom.

So yeah. I’d say we both learned something that day.