Tell us about a time when you felt out of place.

I went to a college with a very high percentage of students who graduated from prestigious New England prep schools. Most had been boarders, rather than day students. In fact, my college was named the #1 “most preppy” college in the country in the wildly bestselling Official Preppy Handbook, which came out in 1980.

I was from an upper middle-class suburban family and attended a competitive public high school. As a college freshman, I wore my Reagan-era preppy clothes from high school, including colorful sweaters and matching Bermuda bags.

I thought I was preppy, but the real prepsters made me feel out of place. My freshman roommate was literally nicknamed Muffy. She was from the Philadelphia Main Line and attended a tiny, prestigious all-girls boarding school. She graduated high school in an expensive white dress, rather than a cap & gown. During our first Thanksgiving break, she went home to attend her debutante ball (aka “coming out” party) in Philly, for which multiple tuxedoed escorts were engaged. It was some real Gilded Age shit. One night she informed me that she had just met her first Jewish person!

In retrospect, the differences between me and the boarding school grads were minuscule. If I felt slightly out of place, I can only imagine how the one and only black student in our dorm must have felt.