The Cruel Philosophr

The Cruel Philosophr

Welcome to "The Cruel Philosophr," the safe place for unsafe conversation. Dive into provocative discussions where no topic is too controversial and no opinion is off-limits. This podcast is your go-to for raw, unfiltered perspectives that challenge the status quo. New episodes are released whenever inspiration strikes, bringing you the most pressing and polarizing topics of our time.

  1. FEB 17

    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.

    25 min
4.8
out of 5
20 Ratings

About

Welcome to "The Cruel Philosophr," the safe place for unsafe conversation. Dive into provocative discussions where no topic is too controversial and no opinion is off-limits. This podcast is your go-to for raw, unfiltered perspectives that challenge the status quo. New episodes are released whenever inspiration strikes, bringing you the most pressing and polarizing topics of our time.