What could possibly go right when a 21-year-old Jewish/agnostic erstwhile hippie chick college dropout and a 55-year-old staid, unhappily married businessman/Episcopal priest fall in love?

Plenty, it turns out.

An Old Man’s Darling is the story of a love affair, parenthood, and a marriage; a 20-year chronicle of the unlikeliest of relationships.

Yes, there is a power differential (and everything that goes along with that) AND the pair love each other truly, deeply, and yes, a little madly, too.

This is a story for anyone who’s ever observed mismatched lovers and wondered what in the world they could possibly see in one another; for anyone who’s ever had a crush on an older man (or woman) and wondered how the fantasy might turn out; and for anyone who understands that sometimes love is just crazy, and that there’s no one-size-fits-all explanation of what attracts one human being to another.

With today’s perspective, and the benefits of both age and hindsight, Shepherd revisits her past, asking tough questions, of herself and about romantic love, religious roots, judgement from others, and feminism, in what becomes a powerful, engrossing and unforgettable read about an improbable love.

“The prose is unflinchingly honest, effectively exploring the roles of body image and self-esteem, religion, and generational differences: ‘Looking back, it all swirls together—objectification/sexual attraction/passion/obsession/possession/desire/intimacy/love—like the tendrils of a sweet pea. If you try to separate them, you are in danger of killing the flower.’ It’s a thoughtful and multidimensional examination of love, power, and self that doesn’t shy away from asking difficult questions. A nuanced and open account of an unconventional relationship.” —Kirkus Reviews

“An Old Man’s Darling pulls triple-duty as a love story, an interrogation of feminism, and a front-row seat to a generation’s worth of significant events in American history. In compelling prose, Shepherd recounts the unlikely story of meeting and falling for a married man 34 years her senior. The story is both joyous and tragic, as most stories are, but readers are allowed inside the author’s awareness of all the ways her personal story might seem to contradict what we think we know about men and women, power dynamics, families, and what love can look like when we’re open to all possibilities. Right until the last page, Shepherd’s story denies us easy answers, and we are better for having lingered in the questions she poses. —Penny Guisinger, author of Shift: A Memoir of Identity and Other Illusions and Postcards from Here

“In An Old Man’s Darling, Deborah K. Shepherd 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 interspersed with letters between the narrator and the man she chose despite society’s—and her mother’s—judgement.” —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

“An Old Man’s Darling is a searingly honest and deeply moving story where Deborah K.Shepherd examines her relationship and marriage to a man 30+ years her senior, and her role in its undoing. 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

“An insightful, tender and generous account of Deborah K. Shepherd’s May-December marriage to her first husband. It’s a tribute and a confession wrapped in a love story, bringing the reader deep into the nuances of youth, aging, and the mysterious power of connection. I didn’t want it to end.” —Blair Glaser, author of This Incredible Longing

“With An Old Man’s Darling, Deborah K. Shepherd deftly braids together the joys, sorrows, and complications of an asymmetrical romance with a man many years her senior. This gripping memoir of Shepherd’s relationship with her first husband provides a moving, emotional ride. Anyone who’s ever fallen deeply for someone whom it seemed, in one way or another, they should not have, will deeply identify with Shepherd and root for her throughout.” —Sari Botton, author of And You May Find Yourself and editor of Oldster Magazine