Rivalries & rituals / Senior prank day, spring 2018, as reported at the dinner table
A Saxophonist Followed Winsor's Head of School Through the Halls
For years, senior prank day at a Boston girls' school had been, by the student paper's account, short on pranks. In 2018 the seniors skipped the permission slip.
Senior pranks at Winsor, the student paper admitted in June 2018, had historically been, shall we say, "prank-less." To prank the school, seniors had to get permission from the head, run their ideas past the administration, set a date and clean everything up by the end of the day. It is the only prank tradition I know with a compliance department.
In 2018 the seniors asked whether they could skip the approval, and, one of them told the paper, the heads were receptive. What followed reads like a countdown.
First thing: the office of the head of the Upper School, filled with colorful balloons, with the top of her head just visible above them as she tried to work.
First period: alarm clocks, hidden in locked closets and hard-to-reach places, going off at intervals.
Assembly: an announcement that there were doughnuts in the cafeteria. There were Dunkin' boxes in the cafeteria. They were full of creepy miniature baby dolls. Meanwhile everyone's backpacks, left outside the theater, had been zip-tied together.
And then, all day, "Careless Whisper" by George Michael, played on the saxophone by a man nobody knew, following the head of school wherever she went. "Needless to say," the student reporters wrote, "their relationship was a tale of unrequited love."
I have tried pranks at home. On April 1 I filled a doughnut box with steamed broccoli and put it on the counter. The youngest opened it, looked at it, closed it, and said, "OK," and walked away, and I ate the broccoli myself, standing up, out of the box, at 7:15 in the morning.
The Winsor seniors had higher ambitions. One explained that the class wanted "an awesome day for the seniors and a hassle for everyone else." They also covered the classroom projectors, which the younger students were thankful for.
The head of school in question, Sarah Pelmas, came out of it famously well. When she left Winsor in 2025 after nine years, a parent who had been a trustee remembered the seniors hiring the saxophonist, and that she took it in stride.
She also took the tradition with her. At her last commencement she told the class of 2025 she had loved sneaking around with them, including "being arrested [on senior prank day] for stealing the lamp." The arrest, I should stress, was staged by students. The lamp was a prop. The saxophonist was never identified.
I am considering hiring one for the youngest's birthday. My wife says she will allow it, if I get approval in advance, run it past the administration and clean up by the end of the day.
Sources
The public records, school pages and published accounts this story draws on. Where the story imagines a scene or a line of dialogue, that is the column’s telling, not a quotation.
- Winsor Banner: Senior Prank Day 2018 — A Revitalized Tradition winsorbanner.org
- Winsor Bulletin: Leading with Love winsor.edu
- Winsor: Spirit shines during Spirit Week, Under the Lights, Head of the Charles winsor.edu
- Winsor: Celebrating the Class of 2025 winsor.edu