The Cruel Philosophr

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


Listen Later

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: [email protected]

Enjoyed the episode? Please leave a 5-star rating and review on Apple Podcasts and Spotify — it really helps the show grow.

...more
View all episodesView all episodes
Download on the App Store

The Cruel PhilosophrBy The Cruel Philosophr