For the second-to-last episode in our private school series, our guest Kayla narrates her journey from a New Jersey public school to the total environment of Phillips Academy — Andover. Growing up middle class in the suburbs, Kayla’s entry into Prep for Prep’s “Prep 9” program meant a 90-minute commute to the big city and a newfound sense of class consciousness. Getting to know her Prep peers, largely from low-income backgrounds, was a lesson in economic inequality.

When she got to Andover, however, the pendulum swung in the opposite direction, making Kayla keenly aware of the privilege she lacked. Black and openly queer by 14, she realizes in retrospect that the institution was not one made for people like her. But boarding school, despite its normalization of whiteness and extreme wealth, was an overwhelmingly positive part of Kayla’s development. Still, Kayla finds that the Prep 9 model is not a scalable one promising meaningful change for the American education crisis.

Other topics include the racial politics of dating in boarding school, the contention over romantic room visitations, and the preppy classics (Vineyard Vines) vs. the American classics (Hollister).