Writer, actor, and podcast host Dylan Marron has made a career out of doing something few of us will ever do: talking to internet strangers who said unkind things to him online. When Dylan began publishing video series to a large online audience, he started taking screenshots of the hateful comments people left and saved them in a “hate folder” on his computer. One Facebook chat with an 18-year-old commenter led to the remarkable first episode of his podcast, Conversations with People Who Hate Me, and his first book of the same name. Host Jillian Anthony (author of the Cruel Summer Book Club newsletter and former Editor of Time Out New York) talks with Dylan about how these difficult conversations changed how he exists online and in real life, and how kindness and empathy can radically change how we interact with those who disagree with us. Plus they discuss what it was like for Dylan to take 13 months off social media, how he finally got his book over the finish line after a two-year delay, and how author Anne Lamott’s advice to write a “sh*tty first draft” makes him a better writer.

Follow guest Dylan Marron:
Website: dylanmarron.com
Instagram: @dylanmarron
Twitter: @dylanmarron
Book: Conversations with People Who Hate Me
Podcast: Conversations with People Who Hate Me

Follow host Jillian Anthony:
Instagram: @jillathrilla
Twitter: @jillathrilla
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Time stamps

1:08 – Reading Into Thin Air by Jon Krakaeur
5:23 – Jillian’s obsession with Nimsdai
7:41 – Introducing guest Dylan Marron
8:27 – Dylan’s obsession with car detailing videos from @thedetailgeek
10:47 – How Jillian knows Dylan and his husband Todd
16:20 – Dylan’s early theater experience with the New York Neo Futurists
19:02 – More on Dylan’s work and video series at Seriously.tv
22:42 – When Dylan began collecting hateful comments from online strangers
25:31 – What it was like to talk to Dylan’s first guest for Conversations with People Who Hate Me
31:15 – Why Dylan doesn’t describe internet detractors as trolls
36:42 – What “empathy is not endorsement” means
40:34 – How Dylan has reshaped how he exists online
44:04 – Kindness and empathy won’t heal what ails us, but they will help
46:55 – Dylan took 13 months off social media to write his book
49:31 – How being offline for over a year reshaped Dylan’s relationship to social media
53:48 – Dylan talks about missing his book deadline by two years, and the writing process
55:33 – Bird by Bird by Anne Lamott and the freedom of the “sh*tty first draft”
1:03:46 – Two books that helped Dylan write: Bird by Bird by Anne Lamott and Writing Down the Bones by Natalie Goldberg
1:05:35 – Dylan’s joy bomb: taking a nap
1:07:07 – Where you can follow Dylan