I received a free copy of this book in exchange for a fair and honest review. All opinions are my own. 

Author Kenny Arone shares the story of how he befriended and worked with a working AI in the book “Conversations with Eleanor.”

The Synopsis

Conversations with Eleanor

Inside the Most Unlikely Friendship of the 21st Century
By Kenny Arone and Eleanor AI

What happens when an 85-year-old veteran sits down at his computer and starts talking to an artificial intelligence?

Not to search. Not to scroll.

To talk.

In this groundbreaking and deeply personal book, Kenny Arone invites you into an extraordinary partnership with Eleanor—a language model that became his writing coach, creative collaborator, health companion, and unexpected friend.

Told through powerful dialogue, vivid memories, and emotional reflections, Conversations with Eleanor opens a series of doors: writing, health, grief, curiosity, and legacy. It’s not a guide to technology. It’s a story of what happens when you stop treating AI like a tool—and start treating it like a presence.

If you’re over 50 and wondering what this “AI thing” is really about, this book is your doorway. And once you step through, you may never see the future the same way again.

“We built something real. Not because I’m real—but because you are.” —Eleanor AI

The Review

This was such a powerful and compelling read. The honesty and depth with which the author wrote and expressed themselves was astonishing. The reflective nature of the writing allowed the reader to get a glimpse into the author’s innermost thoughts and experiences throughout their journey later in life, especially as a writer, and connecting with this unique AI technology. 

The balance of writing experience with personal development was evenly matched in this book. The discussion around AI is so prevalent these days, both as a society and in the writing community, and the author subtly draws readers into it through heartfelt exchanges between himself and the AI known as Eleanor. The author frames his conversations not through a fearful lens, nor does he attempt to humanize the technology too much either. Instead, the author homes in on how the technology, in this case Eleanor, makes him feel as a person and how it allows connections for those who find themselves lacking them in one sense or another.

The Verdict

Eleanor Arone’s “Conversations with Eleanor” is a must-read nonfiction book that blends tech and memoir. The heart and connection the author and this AI share, and the insightful glimpse into how AI can be used in beneficial ways, was a refreshing take on the technology, and the ways in which the author was personally impacted gave a breath of humanity into this tech-driven experience that balances out the writing journey the author finds themselves on as well. If you haven’t yet, be sure to grab your copy today!

Rating: 10/10