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My Father’s Widower

My Father’s Widower

esquire.com 12.10.2026 13:00 6 views
When the author’s dad died, he left behind a younger husband. There was no question that the man was kin. But what if he were to remarry? A story about what family really means.

No expectations or pressures, just possibilities.” The personal ad, published in The Stranger, the ’90s Seattle indie rag of record, caught my father’s eye. He was 44, but age didn’t stop him from calling. Years earlier, 31-year-old Bill Bailey Carter had been a rising star in the southern advertising world, producing commercials that starred Orson Welles.

By 39, his agency—and his marriage—had fallen apart. He moved to Seattle to start over, and I moved with my mom to Fairfield, Iowa. As I entered my teenage years, I sought something she couldn’t provide: a model for manhood.

So the night before I started eighth grade, I moved west to live with my dad. I still didn’t know the real reason behind my parents’ divorce, but as I met my dad’s many, many new guy friends, questions filled my mind. He sat me down one afternoon in our Capitol Hill apartment and said, “I need to talk to you about the fact that your father is gay.” Our duplex became a gay social hub with an open-door policy seven nights a week.

When I was 16, he began dating a 19-year-old University of Washington sophomore. The guy eventually moved in with us, and he competed with me for my father’s attention in a strange, sibling-rivalry kind of way. After the better part of a year, he left my dad for another man, and I was left to clean up the mess.

Bill Bailey wallowed in the heartbreak by listening to A Little Touch of Schmilsson in the Night while gulping down red wine. The “merlot period,” as we would later call it, was well behind him when he called the number on the personal ad. The man on the other end, a 26-year-old named Jamie, had already received more than 50 voicemails, but something about my father’s north-Louisiana drawl set him apart from the other guys.

They quickly set a blind date. On Monday, July 15, 1996, my father came downstairs in a whiff of Armani cologne, dressed in khakis and a white oxford shirt with the sleeves rolled up to show off his forearms. But if I like him, I’ll take him to Discovery Park.” He didn’t come home until the next morning.

Extract — continue reading at the source.

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