The short answer is that I wanted to help people celebrate the unexpected friendships in their own lives, especially the ones that go back years or decades. Why did you want to write this book, about an unexpected friendship with a college friend? I caught up with Will to ask about his inspirations, his thoughts on our hyper-polarized world, and what his old pal really thinks about being the subject of a book. Though the two couldn’t have been more different in their backgrounds and passions, the tight-knit friendship they formed has grown and endured over decades. Will’s new book We Should Not Be Friends: The Story of a Friendship explores an improbable connection he made with a classmate at Yale. (Will’s syllabus alone - from Stuart Little to Girl on the Train to Rebecca to Song of Solomon - is remarkable and fun you’ll thoroughly enjoy the literary ride alongside him.) Will followed that up with 2016’s Books for the Living, in which he told his very personal story through the lens of the books he was discovering along the way.

His first book, the 2012 New York Times bestseller End of Your Life Book Club, told the story of his relationship with his remarkable mother, Mary Anne Schwalbe, through the books they shared together during the two years before her death from pancreatic cancer. (Katie calls me the self-appointed president of the Will Schwalbe Fan Club).

Will’s first two books are both on my “favorites” list. He’s a New York-based editor, writer, and pop-culture expert extraordinaire who became friends with my older brother Tom at Yale - and they’ve remained close ever since. I don’t just love Will Schwalbe’s writing - I’ve considered him a close friend for 40 years now.

Conversation with friends book