Jonathan Zimmerman, a professor at the University of Pennsylvania and author of "Free Speech and Why You Should Give a Damn", discusses vital topics around free speech and its challenges in today’s society. He emphasizes the importance of engaging with opposing views and cultivating critical thinking in education. The conversation also touches on the toxicity of social media, the historical context of censorship, and how personal experiences shape perspectives. Moreover, they explore the evolution of communication and the implications of emerging technologies on free expression.