Hey everyone,

Years ago I was browsing through a bookstore when I stumbled on a small purple book called 'I'm Afraid of Men' by Vivek Shraya. I flipped it open and was transfixed.

It showed me a view and a lens and a perspective I had no familiarity with. I ended up buying more of Vivek's books, including A Boy & The Bindi, and when her live memoir stage show How To Fail As A Pop Star visited Toronto my wife Leslie and I bought tickets and joined the giant standing ovation.

Since we recorded this conversation, Vivek's work has expanded across books, music, theatre, TV, film, and fashion. She created and wrote the CBC Gem adaptation of How to Fail as a Popstar, which premiered internationally at Cannes and went on to win Canadian Screen Awards for Best Web Program or Series and Best Writing. She is now a three-time Canadian Screen Award winner, released her eleventh solo album New Models in 2025, an alter ego project VIVICA earlier this year, and her thirteenth book, the dystopian novel 'The Hystericals', arrived last month. 

Vivek navigates complex topics—topics most people aren't willing to discuss—with a comfort and clarity that shows deep thinking, partly resulting from the hardships she's endured and navigated throughout her life. 

In this conversation we talk about how parents can avoid snuffing out their children's gender creativity, how we might think about pronouns, traditional trans narratives, and how loving others can teach us how to love ourselves. I loved talking to her and hope you enjoy this conversation as much as I did.

Let's flip the page back to Chapter 53…

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