Episode 185: Worst Boyfriend Ever Read in NYC. I Was There.

Worst Boyfriend Ever — one of Substack's most controversial and compelling writers — did a live reading in NYC, and I was there. I took the 2 train down to 14th Street on a Saturday night, something I haven't done solo in maybe a decade, and walked into a packed bar that was definitely not built for 120 people. WBE read offensive material while people walked out mid-reading in protest. He threw books at audience members. He didn't flinch once. What I left with wasn't just a recap of a wild night — it was clarity about the crowd I want to be around and what fearlessness actually looks like in practice. Timestamps: 1:40 – Intro and call for ratings/reviews 3:06 – How I discovered Worst Boyfriend Ever on Substack 4:28 – Arriving at the bar, navigating to the reading space 8:27 – WBE takes the stage and reads chapter one 10:20 – People start walking out mid-reading; WBE starts throwing books 13:14 – Danny Lee reads (the best reader of the night) 13:57 – The Indian girl reads from her phone 16:19 – The Amsterdam dude reads and works the crowd 17:49 – The Louis CK lookalike laughs at his own jokes 19:43 – WBE returns: "Why I Like Asian Girls" and "Why You Shouldn't Love Women" 20:52 – Closing thoughts on finding your crowd and overcoming fear Links: Worst Boyfriend Ever on Substack: jamesguilty.substack.com Contact: cruelphilosophr@gmail.com Enjoyed the episode? Please leave a 5-star rating and review on Apple Podcasts and Spotify — it really helps the show grow.