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book cover for AN OLD MAN’S DARLING: A Memoir

AN OLD MAN’S DARLING: A Memoir

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Pub Date May 12 2026 | Archive Date Not set


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Description

In her captivating memoir, Deborah K. Shepherd examines her first great love, with a man thirty-four years her senior. In 1968 and at age 21, Shepherd ditched college in Tucson for hippie life in New York. When that soured, she found a low-level corporate job, where she met Bill Shepherd, an unhappily married, 55-year-old senior executive. That they had a fling is unsurprising for the time. What is surprising is that they stayed together, for twenty years and two children, despite their age gap, differing religions, and society’s expectations.

With today's perspective, and the benefits of both age and hindsight, Shepherd revisits her past, scouring old letters and asking tough questions, of herself and about romantic love, religious roots, judgement from others, and feminism. But she offers no easy answers in what becomes a powerful, engrossing, and unforgettable read about an unlikely love.

In her captivating memoir, Deborah K. Shepherd examines her first great love, with a man thirty-four years her senior. In 1968 and at age 21, Shepherd ditched college in Tucson for hippie life in New...


A Note From the Publisher

DEBORAH K. SHEPHERD’S first novel, So Happy Together, was published in 2021 when she was 74. Her essays have appeared in Oldster Magazine; Fauxmoir; Motherwell Magazine; Herstry; Eat. Darling, Eat; Persimmon Tree, and more, and her Covid-themed essay was a winner in the Center for Interfaith Relations 2020 Sacred Essay Contest. A retired social worker, she spent much of her career focused on the prevention of domestic violence and sexual assault and the provision of services to survivors. The mother of two and grandmother of two, Deborah lives in Maine with her husband and one sweet, jaunty rescue dog.

DEBORAH K. SHEPHERD’S first novel, So Happy Together, was published in 2021 when she was 74. Her essays have appeared in Oldster Magazine; Fauxmoir; Motherwell Magazine; Herstry; Eat. Darling, Eat;...


Advance Praise

“...a thoughtful and multidimensional examination of love, power, and self that doesn’t shy away from asking difficult questions." - KIRKUS REVIEWS

"...gripping...a moving, emotional ride." - SARI BOTTON, editor of Oldster Magazine

‘…searingly honest and deeply moving….A free-spirited, young woman with low self-esteem, Shepherd falls madly in love with the middle-aged, unhappily married man steeped in the corporate world, both of them hungry for that life-affirming validation of being truly seen, desired, and understood. From the wild passion of the early years, to the money troubles and squabbles of domestic life, to the inevitable and harsh reality of time catching up to the couple’s magical thinking, it is a testament to the mantra that “age is just a number,” until it becomes much, much more.”- Nina B. Lichtenstein, author of Body: My Life in Parts

“…captures the spirit of a young woman who falls madly with every bone in her body in love with a married, mature colleague. Despite their huge age difference and differing religious backgrounds, their love lasts. What could have ended up a disaster is a surprising story with the usual—and unusual—ups and downs. A heart-capturing tale…” - Jennifer Lang, author of Places We Left Behind: a memoir-in-miniature and Landed: A yogi’s memoir in pieces & poses

“This is a compelling read about a May-December relationship and all its pitfalls. From the intoxicating beginning to the disturbing ending, the author pulls the reader inside her long love affair and marriage to a much older man.” - Kate Walter, author of Looking for a Kiss and Behind the Mask

“...a thoughtful and multidimensional examination of love, power, and self that doesn’t shy away from asking difficult questions." - KIRKUS REVIEWS

"...gripping...a moving, emotional ride." - SARI...


Available Editions

EDITION Paperback
ISBN 9781956474831
PRICE $22.00 (USD)
PAGES 294

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Featured Reviews

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I was immediately drawn to this book by the cover and title. I always say I love older men, and I enjoy reading stories about women’s relationships with them. I enjoyed Shepherd’s memoir about her life, romance, and the ups and downs involved with the love she finds. The writing is effortless and sucked me in! Thanks to NetGalley for the ARC.

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I couldn’t put this memoir down. It took me just a few days to finish and I don’t typically read that fast. The story was brilliantly woven. All the scenes unfolded like a movie. I was right there in NYC in her tiny apartment and library. I could almost smell the food she was eating during her rendezvous with her lover. I could feel the slip of the car tires against the snow out west. And I could see the unfinished kitchen and untouched walls in her Hudson Valley Home. I loved the way the author braided love letters from yesteryear with her own personal thoughts. I cried at the end. The author bears her heart on the page. Her life advice touched me immeasurably and made me cry again. Like any human, she has things she’d like to go back and adjust. I admire her candor on loving with wild abandon and the sacrifices and hardships she endured to find herself again. FIVE STARS.

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This memoir tells the story of Deborah K. Shepherd’s unconventional love story with a man much older than her. She shares her experiences with honesty and reflection, looking back on their twenty years together and the challenges they faced. The book thoughtfully explores love, age differences, religion, and social expectations. It’s an honest and engaging read that stays with you. I recommend this book to all public libraries to purchase.

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