Talking Across the Divide: Dylan Marron on Radical Empathy and Difficult Conversations

Kashmala Khan ’29

Managing Editor

When writer, podcast host, and digital media producer Dylan Marron visited Trinity College on March 5, he offered students and faculty a challenge that felt both simple and radical: talk to the people you disagree with.

The discussion was hosted by the Office of Community and Belonging as part of the campus’ inaugural Spring Read initiative, which features a book selection centering personal growth to cultivate meaningful engagement across differences. Marron’s talk in the Washington Room was based on his book, “Conversations with People Who Hate Me: 12 Things I Learned from Talking to Internet Strangers.” Based on his podcast of the same name, the book documents Marron’s unusual experiment that involved contacting strangers who left him hostile messages and asking if they would be willing to converse.

Marron began by describing how the podcast and book emerged after his digital projects brought him attention, such as his early video series, “Every Single Word.” As these productions gained popularity, Marron began receiving waves of criticism and insults for them. Initially, he coped by screenshotting the comments and saving them in what he jokingly called a “hate folder.” 

Over time, curiosity replaced frustration. Because many comments came through social media platforms, Marron could see the profiles behind the messages. “I started leaving backstories for these people in my hate folder. It made me feel like it wasn’t some distant monster who was saying this stuff to me, but a human,” he said.

Eventually, he began contacting some of these individuals. With their permission, he recorded the conversations, which later became the foundation for his podcast and book.

Throughout the evening, Marron shared several insights from these conversations.

The first, he delineated, is that “social media is a game.” Online platforms have penetrated our lives to an extent that we seek validation through clever responses or public approval. Comparatively, conversations require a different mindset. “A conversation is the opposite of a game—it’s a relationship,” Marron said.

Another challenge he described was the tendency to discuss too many disagreements at once. Marron called this phenomenon the “everything storm,” elaborating that meaningful dialogue becomes impossible when individuals try to address every ideological difference simultaneously.

Language also shapes how people interpret conflict online. Marron noted that he initially labeled all negative comments as “hate,” even though they varied significantly in intensity. “The word hate is too big,” he said; mild criticism and extreme threats often become grouped together online.

Marron also challenged the concept that disagreement must always lead to debate. “Debate is our default,” he said. “But debate is a spectacle of opposition that promises a winner and a loser.” His podcast instead focused on understanding the other person’s perspective and avoided debate. This approach frequently led to empathy, which Marron categorized to be necessary yet misunderstood.

“Empathy is the necessary fuel that gets the conversation off the ground,” he said. At the same time, he emphasized that empathy does not require agreement. “Empathy is not endorsement,” he asserted.

However, it is pertinent to establish that not every conversation resulted in understanding. Marron shared examples from the podcast where discussions were futile and ended in frustration or disagreement. Yet, he stressed that “change takes time.” Indeed, some participants later revisited their conversations and reconsidered their positions.

An additional lesson emerged when Marron postulated that criticism from people within one’s own community can feel more painful than comments from strangers. He believes that conversation can play a crucial role in reducing what he called “shame culture.”

Despite acknowledging some of the limits of dialogue, Marron argued that conversation remains a powerful tool in a polarized world. “A conversation builds a bridge where there wasn’t one before,” he said.

For the Trinity students and faculty participating in the Spring Read program, the talk offered both a reflection on online culture and aimed to provide a reminder that difficult conversations, while imperfect, can still create opportunities for understanding.