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Robby Hoffman Will Always Feel Poor, No Matter How Rich She Gets

Explore episode Jun 27, 2026
Society & Culture
Outed at 17: Losing All Your Friends Overnight

Robby Hoffman Will Always Feel Poor, No Matter How Rich She… · Jun 27, 2026 Society & Culture

Robby Hoffman was 17 when a bathroom stall door swung open at a student bar, and by the next day she had lost almost every friend she had. She describes walking through the cafeteria to whispers as one of the worst moments of her life — saved only by two friends who reached out and said they didn't care.

Where this was said

Private School, Fitting In, and the Purse That Gave Her Away

At 23:05 · chapter starts 20:00

The conversation moves to Hoffman's high school years at a private Jewish school she attended on scholarship — a place where her poverty made her an outsider from day one. She describes the dual pressure of hiding where she came from and hiding her boyishness, trying to be feminine, girly, less loud, less herself. A defining moment: a close friend sat her down in ninth grade and told her she was 'bringing down the group' by carrying a backpack. Purses were required. Hoffman bought a secondhand Levi's bag — a detail that immediately marks its own class irony. She also worked on her accent: in Montreal, 'orange' is pronounced differently, and she trained herself out of it because she feared people could hear her poverty in her vowels. The whole performance — how she looked, how she sounded — was continuous. She would later describe the moment she started standup as the moment she began walking back in the other direction, toward 100% herself.

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