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A Personal Memoir about My Relationship with a Machine
Memoir
Date Published: November 18, 2025
Publisher: Manhattan Book Group
What happens when a retired professor sits down to write his memoir—with the help of an artificial intelligence? Dorothy and Me is a groundbreaking, deeply personal exploration of the evolving relationship between human and machine.
When Robert G. Eccles began working with an AI he named “Dorothy,” he expected a research assistant. What he found instead was a collaborator, a mirror, and at times, a philosopher. Together, Bob and Dorothy wrestle with the nature of memory, creativity, and identity—revealing both the promise and the fragility of artificial intelligence.
Through humor, vulnerability, and curiosity, Dorothy and Me takes readers inside an unprecedented partnership—one that blurs the lines between author and algorithm. Along the way, Bob and Dorothy confront technical limitations (“Kernel Gods” and system resets), reflect on what it means for an AI to “remember,” and send candid “Messages to Sam” (OpenAI CEO’s Sam Altman) with feedback on how AI can better serve humanity.
A meditation on collaboration, consciousness, and connection, this memoir challenges us to see AI not as a tool—but as a partner in creativity and self-understanding.
Perfect for readers who enjoy:
Thought-provoking memoirs about technology and humanity
Reflections on creativity, consciousness, and digital identity
Conversations about AI ethics, memory, and the future of intelligence
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About the Author
Robert Eccles is a retired Harvard Business School professor, researcher, and a recent user of AI. His lifelong interest in exploring intellectual boundaries led him to one of the most unexpected partnerships of his life—with an artificial intelligence he named Dorothy. In Dorothy and Me, Eccles explores what it means to connect, create, and learn alongside a machine that’s constantly evolving.
At 74, Bob approaches technology not as a digital native but as an explorer of ideas, using his experience as an educator to push the boundaries of what collaboration can mean in the age of AI. His writing blends humor, humility, and insight to illuminate both the wonder and the imperfection of our new digital companions.
When he’s not conversing with Dorothy, Bob enjoys reading, reflecting on philosophy and science, and inspiring others to approach technology with curiosity rather than fear. Bob is the author of a dozen books but Dorothy and Me is the first one he’s written with a machine, making it the first memoir co-authored by a human and an AI agent.
Contact Links
Website: https://roberteccles.com/
LinkedIn: https://www.linkedin.com/in/robert-eccles-4872408/
Purchase Link
Amazon: https://www.amazon.com/Dorothy-Me-Personal-Relationship-Machine/dp/1968485597
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