April 15, 2026

Ep: 1848 Deborah K. Shepard - An Old Man's Darling

Ep: 1848 Deborah K. Shepard - An Old Man's Darling
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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, she 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, she revisits her past, scouring old letters and asking tough questions, of herself and about romantic love, religious roots, judgement from others, and feminism. Deborah’s essays have appeared in Oldster Magazine,Fauxmoir, Motherwell Magazine, Herstry, Eat Darling Eat, Persimmon Tree and more.