“I Drink Milk,” read the headline, a young man’s clever way of saying he was just a regular guy. “You’re 25–40 and not afraid to be yourself. 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.
A scan of the ad that led the author’s father to Jamie.
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.
“I won’t tell him I packed a picnic,” he said. “So if he’s a dud, I can bail after a coffee. But if I like him, I’ll take him to Discovery Park.”
He didn’t come home until the next morning. Six months later, on a Valentine’s Day trip to Disneyland, he asked Jamie to move in. My dad had his faults, but he never lacked the courage to follow his heart.
“I went to the most incredible wedding last night,” my father said.
It had been more than a year since Jamie moved in. I was in college in upstate New York; they were in Greece to celebrate my dad’s 46th birthday. Through my dorm-room phone, I listened to him describe an intimate ceremony in castle ruins on a Santorini hilltop attended by villagers and a few stray dogs. He spoke of a dreamy reception at a piano bar where they drank Dom Pérignon and ate wedding cake decorated with pomegranate seeds.
“Whose wedding was it?” I asked.
“Ours,” he said.
I was speechless. Just knowing how bold and spontaneous he was, I shouldn’t have been surprised by the sudden nuptials, but I was. I’d learn later that marriage was important to Jamie. Without it, he told me, their relationship was an open door that my father could slip through.
At least I took the news better than Jamie’s own father. “Are you telling me I have a 46-year-old son-in-law?” he snapped. Bill Bailey would win him over soon enough.
In the spring of 2011, I was living in Los Angeles and single after a bad breakup. My dad and Jamie were renting a house in Key West and encouraged me to crash in the spare bedroom for a couple weeks.
On my second-to-last night, at a bar called Durty Harry’s, I met a Clemson senior on spring break and fell in love. Always the one to nudge me off the edge of the diving board, my dad egged me on: “Why not toss out your return ticket, see where things with this girl might go?” Jamie agreed: “You never know.”
Four years later, Susan and I were married and living in Charleston, South Carolina. My dad and Jamie followed us, hoping for grandkids. They bought a house in Beaufort, a nearby waterfront town lined with ancient oaks and Spanish moss. My dad opened an antique shop on Bay Street, and everything seemed perfectly in place for his next act.
But he didn’t know how to slow down. When he got sick with double pneumonia, I knew it was because he was pushing himself to exhaustion at the store. His nightly double bourbons on the rocks didn’t help, either.
“I won’t tell him I packed a picnic,” my dad said of Jamie before their first date. “So if he’s a dud, I can bail after a coffee. But if I like him, I’ll take him to Discovery Park.”
Jamie and I took turns visiting him in the hospital. Even with oxygen tubes in his nose, he kept his sardonic humor. “Get that muskrat ballerina out of my sight!” he said, glaring at a tutu-wearing stuffed mouse that came with a get-well card.
Bill Bailey Carter died on May 12, 2016, at the age of 64. Susan and I stayed with Jamie on and off for weeks after. We navigated grief together, wondering what our relationship would look like without my father connecting us.
In the wake of my dad’s death, Susan and I developed a mantra: “What would Bill Bailey do?” The answer was, of course, to embrace life. In the first week after losing him, we bought a house, sight unseen, and conceived our first child. Nine months later, our daughter came into the world bearing his middle name.
Jamie was at the hospital right alongside her other grandparents. What would she call him? Grandfather wasn’t right. Jamie wasn’t right, either. When he married my dad, I faced a similar dilemma. He wasn’t that much older than me, so stepfather sounded strange. Instead, I called him my Stepmonster. With that, it was decided: Jamie would be her Grandmonster.
This article appeared in the October/November 2026 issue of Esquire
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Two years later, Jamie met Steve on a dating app. On their first date, they felt an undeniable connection. In 2022, they bought a house together in Savannah, and my family, which had grown by one more child, began to spend holidays with Grandmonster and Steve. The kids would set crab traps in the marsh with Steve and watch movies with Jamie, growing closer with each visit.
“I wish we could live with our grandparents all the time,” August, my six-year-old son, once told me out of the blue. Grandparents, he called them. Though they shared no blood, they were his grandparents.
A few months ago, Jamie and Steve broke the news that they were moving to Mexico. They were ready for a new chapter in their lives but wanted our help with one last detail—an important one. Jamie and Steve asked Susan, an attorney and registered officiant, to oversee the signing of their marriage license. The ceremony would be intimate: the two of them, Susan and me, and their grandkids.
The author’s daughter stands between Jamie, right, and his new husband, Steve, after their nuptials in July 2026.
On an auspicious July day, almost exactly 30 years after he met my father, Susan walked Jamie down the aisle in our backyard to marry the next love of his life. As Jamie and Steve sealed it with a kiss and a toast, I suddenly wished my dad were there with us. Later, as I snapped a picture of his namesake granddaughter standing between the newlyweds, I realized that he was.
He was there in the romance of the moment; in Jamie’s boldness to follow his love story wherever it took him; in the life I’d made with Susan from that chance encounter in Key West; in our children understanding more about family than we could ever teach them.
I now know why Jamie’s personal ad caught my father’s eye. It reflected him at his best—how he wanted love to be. And if I’m paying by the word, I’ll pass on its most important lesson about life and love to my children: “No expectations or pressures, just possibilities.”
Lead image: The author’s father, right, exchanging wedding rings with his husband, Jamie, on the Greek island of Santorini in September 1997.