What Uncle James’ Heartbreak Taught Me

My gay uncle came out even though it meant my family rejected him. But he found a love that endured despite the odds.

Photo by Nik on Unsplash

“If you called to give me shit about being gay, I’m going to hang up on you now,” my uncle blasted across the phone line.

His words sliced me into silence. I choked the receiver, confused and hurt, until I remembered: After three years of living in Manhattan, I’d developed some verbal Taekwondo of my own.

“I’d only care if you’re gay if I wanted to date you, which I don’t,” I replied. “I called to ask if you knew Harvey Milk?’

He huffed hard. “Your dad didn’t have you call me?”

“I doubt my dad even knows who the hell Harvey Milk was,” I responded. “I just saw a documentary about him, and you lived in San Francisco in the ’80s.”

The line took on a bruised silence as I imagined my uncle quivered with calculation, mental rummaging. I heard a soft exhale, then, in a low voice, he said: “I’m sorry, I just assumed you were being JW’s daughter. Yes… I knew Harvey.”

I last heard my uncle’s voice 20 years before, about the age of seven. We first met when I was five, and the moment remains legendary in Holmes family lore. As he strode up the walkway of our two-story, brick-home on the westside of Detroit—his bold stride reinforced with a chiseled jaw and deep brown eyes—clad in a crisp, white sailor suit, he seemed like a Disney movie prince. I stood agape. But John, my younger brother, ran to our uncle yelling: “Daddy, Daddy, Daddy!” He looped his thin caramel arms about his white trousers, mesmerized.

As a child, I marveled at seeing my father and uncle together. Nearly mirror images of the other_, the same Arkansas-bass-loaded voice, the same head tilt when they laughed, as they reconnected over plates of food at our dining room table, it was jaw-dropping. The closest I ever came to witnessing a real-life doppelgänger in the flesh.

But even children can wield the gift of sight. I knew they were brothers, yet different varieties of men. My father was a bespoke Black man, a traditionalist to the point of puzzlement. A man who wore retired wing-tips to mow the lawn while dressed in overalls. Uncle James, in contrast, deployed a charming, unguarded sweetness, the kind that made girls swoon. Still, a girlfriend never appeared on his arm during visits. Fine by me. More time for me.

Sometime during the ’70s, Uncle James received his discharge from the U.S. Navy. Rather than settle in Detroit, he moved to San Francisco. With that, the visits, the calls, the Christmas cards, stopped. And it would take Harvey Milk to reveal why.

The Holmes Family hold graduate degrees in keeping secrets. Years later, I’d learn that Uncle James left one war behind but came home to another battlefield. After his time of service, his freedom must have meant much more to him. So, he came out to the family. Everyone except his eldest sister, Vera, surgically removed him from their lives. My father never spoke his name again.

But after seeing the PBS documentary on Harvey Milk, late one night in the 1990s, I couldn’t let it go. I talked about the legacy of Milk to anyone who’d listen. As he’d famously said in 1978 in what is known as the Gay Freedom Day Speech, “Gay brothers and sisters, you must come out. Come out to your parents. I know that it is hard and will hurt them…” Uncle James had, and it did.

“You should call your Uncle James,” Aunt Vera said. “Ask him about Harvey Milk yourself. I have his number.”

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Some moves are so smooth, you don’t even see them made. My aunt set me up, but it took years to see her mastery. As a big sister to James, she made it her mission to rebuild a bridge long since charred. And a wayward daughter, prompted by the ghost of Harvey Milk, was the perfect balm to heal the family wound.

“So, you really knew Harvey Milk?” I pressed.

“Sure, I voted for him.”

“Really?”

“I lived in his district.”

“You met him?”

“Saw Harvey all the time. He was a big part of the community.”

“It’s cool that you knew him.”

“He was a cool guy to know.”

My uncle and I didn’t stop at Harvey. Our conversations continued. Every few weeks, I’d reach out to him, or he’d call me to discuss everything and nothing: family doings; what I prepared for dinner (frequently ramen), versus the proper meals he prepared: meat and potatoes, always accompanied with a dessert. I discovered he shared these dinners with a man named Bob. They had a collection of small dogs that they babied and fretted over. I shared my life as an art student at Parsons in New York City, my jaunts going to gay bars supporting my newly outed friends.

“How can you enjoy a gay bar that much?” my uncle asked. “You’ll never meet a guy that way.”

“The drinks are good, the music’s better, and everyone wants to dance.”

My uncle bellowed into the phone receiver: “You’re a good friend!”

When I did finally meet a guy, I found him in an equally surprising place. After a bad blind date ended poorly, he hailed a taxi. I got in. My date didn’t. I gave my address to the cab driver, then stared out of the window. As the cab whizzed up Amsterdam Avenue, I felt relieved to be free of my mismatched companion. The driver watched me through the rearview mirror. We chatted. By the time the taxi had gone from West 72nd to West 86th Street, we’d shared an astonishing conversation. This guy had an intellect.

“I don’t just drive a cab,” Arthur said. “I’m finishing up undergrad at NYU.”

He asked for my number, and I gave it. We dated. We fell in love. Our months dating felt joyous, and then Arthur announced his plans to attend Stanford Law. As an artsy girl, I leaned heavily into East Coast life, and I wanted no part of being a “law school widow.” But I fell hard for Art. After a year of care packages and emails, Art returned to New York City for his summer internship at a top law firm. By the end of August, he decided he couldn’t let me go.

“Come to Palo Alto and see things for yourself,” he said.

“OK, but with one condition: I want to visit my Uncle James.”

“Do we have to see your uncle?”

“Yes, and his boyfriend,” I replied. “I haven’t seen him since I was a child.”

Art groaned about visiting relatives, but, in time, agreed. So, after a flight out West, a tour of Stanford’s beautiful, brown stone campus buildings, and the majestic redwoods in Palo Alto, Art and I drove to San Francisco to have dinner with my uncles.

We met them at an eatery near the City Lights Bookstore. I wanted to go inside the legendary bibliophile mecca that rivaled The Strand, but I longed to see my uncle more. When Art and I arrived at the Japanese restaurant, Uncle James and his partner were already seated. His face brimmed with pride. I had really shown up! We were having a family meal together, at last.

I remember sitting across from Bob, eyeing his freshly shaved face, the scattered rough red patches that dotted his pale cheeks, his thinning chestnut hair shaped in a firm comb over. Both he and my Uncle James wore crisp suits.

“They dressed up for us,” I thought. They looked like cute jelly beans sitting side by side—James, my Black uncle, and Bob, my new white uncle—their chubby fingers laced into a beautiful lattice of pink and brown on top of the table. I never thought to ask Bob’s race. The hue of his skin didn’t matter. My uncle’s happiness mattered.

The sushi dinner was fresh and fanciful. My uncle watched with delight as I wielded my chopsticks. We had to be the only two people in our family who could use them—or would even try.

“You want to come over for dessert?” Uncle James asked.

I nearly jumped out of my seat, as Art’s body slumped into mine. Our universal signal of’ “no.” But later, when he saw they had his favorite ice cream, butter pecan, he softened. We sat in the living room to enjoy all manner of treats—blueberry pie, butter cookies—as the dogs leapt all around us. Bob and James sat on their plastic-sealed French Provincial living room furniture, like it was a mini-Versailles in the hills of San Francisco. It felt magical.

When I returned to New York City, I called my mom and gave her an update. Her answers arrived in monosyllables. “That’s nice” and “oh yeah.” Her nonchalance was unbearable. By the ‘90s, after 20-plus years of being together, my parents had divorced. Uncle James had a union almost equally as long with Bob, and that seemed worthy of celebration. My relatives didn’t find that a point to celebrate.

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About a year later, Aunt Vera called. “Have you tried to reach your Uncle James lately?”

“The phone just rings, the machine picks up,” I explained. “I leave a message; he doesn’t call back.”

“Honey, there’s a reason why. I have some bad news. Bob had a heart attack. He didn’t make it.”

“What? When is the funeral? I want to go!”

“No, your uncle doesn’t want any company.”

I continued to call. He continued to not answer. Confusion wrecked my brain. After a month, I decided to act.

“I’m flying out to see Uncle James,” I told Aunt Vera. “I know he’ll open the door for me.”

“Honey, he won’t.”

“How do you know?”

“He started drinking again. He’s not going to want you to see him like this.”

“Again? What do you mean again?”

I knew of my uncle’s love of dog sweaters, and his habit of sending flirty eyes towards couples that men wrongly interpreted as directed to the women dangling from their arms, but he never defined himself as a Friend of Bill’s. So excited by our dinner, I took no note if he was sober, sipping water to my wine, or tea to my sake.

Uncle James had been the fun version of my dad, until he wasn’t. Until he lost the love of his life, and his heart became so broken he believed only alcohol could fill the cracks. Until alcohol killed him.

Such heartbreak is unimaginable unless you’ve had it foisted upon you. I would learn this lesson after Art moved from the dorm into an apartment, so he'd have more privacy, so maybe we could have a place together, when I moved. If I moved. And when a regular cold became deadly serious, became pneumonia, Art died alone in his bed. He was only 26 years old.

Like my uncle, I discovered that a heart can shatter, and the shards can break into even smaller, sharper weapons set on destruction. My family flew my brother from Detroit to Manhattan to keep me away from the working gas oven and the knives. And I faked acceptance, for a week, until I could be alone, until I could set about drowning my grief and guilt in red wine. If only I had been there, if only I could’ve called 911. It’s the if onlys that wreck you.

Just as my uncle had, I left the phone unanswered. I wanted no lifeline, no listening ear. Now I understood my Uncle James on a unique level. No matter who waited on the other end, they didn’t have the power to bring back the men we love.

Unlike my uncle, however, I couldn’t completely ignore the daily pleas left on my voicemail. And once my loved ones heard my voice, and what it carried, they mobilized, pushed me into therapy and saved my life.

My Arthur is gone. My uncle is gone. Bob is gone. Harvey is gone. All of the boys that I danced and celebrated with in the bars of the West Village are gone too, fallen by AIDS. One word comes to mind when I think of the 1990s: sorrow.

Yet, when I wander through the maze of memories shaped in the streets of the West Village, I come alive. I smile at the same-sex couples with spreading midsections. I admire their gelled, graying comb overs. In them, I see my Uncle James and Bob in their strident love. I wander back to remembering, to hold on to what’s important to your life, because it holds you.

That’s one thing that my experience with Uncle James taught me: A great love carries on, one way or another. Sorrow exists in the world. Sometimes it’s your turn to experience it. It will track you down. And it did. But I brought my experience with me, my uncle’s loss. So, when I fell into the same pit of grief, I recognized the darkness, its crushing effects. We both lost the men we loved. My uncle couldn’t fight through it. So, I knew it mattered that I found a way forward for both of us.

Knowing my uncle changed everything. While I hold pride knowing he knew an icon, a pioneer who mattered to history, the love he shared with Bob matters more. Our dinner remains a highlight of my life. I wish we could’ve had more. Still, it scares me how close I came to having shared no dinner at all. My life-altering experience came from picking up the phone. From having the courage to reach out to my uncle, and him having the courage to reach back. In this high-tech world, I remind everyone, picking up the phone, at times, can matter more than you’ll ever know.

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Jenine Holmes’ byline has appeared in The New York Times, The Detroit News, Forbes, Creative Non-Fiction Magazine, New York Press, and recently Cable Street. She has an essay in an anthology on Toxic Workplaces to be published in 2025.

As an advertising Creative Director and copywriter for two decades, Jenine has worked with Fortune 500 brands, including Pepsi, Jaguar, McDonald’s, State Farm, The NBA on TNT, and more. Her experience has led her to win awards and work for two legendary creatives: the design visionary Milton Glazer and filmmaker and social iconoclast Spike Lee.

Jenine received her undergraduate degree from Parsons School of Design and an MFA from the Naslund-Mann Graduate School of Writing at Spalding University. She serves as an adjunct professor at the New York campus of the University of Texas, with a focus the social intersectionality of advertising, marketing, and PR.

She lives on the Upper West Side of Manhattan with her daughter Julia and Iris the Wonder Dog, a terrier-schnauzer mix.

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