My Gay Cayman Life

in Graynd Cayman, January 2020


Two young women holding hands, skipping in the sand, a rainbow kite trailing behind them catching in the wind. They stop, turn and kiss each other. Two photographers click their shutters, capturing every moment. 

“They’ve just become engaged,” explains one of the photographers in an American accent. 

“Congratulations,” I say as the women pass.

“Thanks,” the women say in unison, without looking at me, only looking at each other, arms so entwined it’s hard to tell whose limbs are whose.

I watch as the group moves down the beach, the photographers taking picture after picture, turquoise waves rolling in the background. It’s a perfect day. Azure sky, palm fronds rustling, calm sea. I just pray there is no one around who will say anything, do anything to wreck their loving scene.


“Those women must have been either brave or foolish,” says my grandmother after I get back to her little yellow condo and tell her about the couple. “Grand Cayman is still very conservative.” 

My grandmother is 90 and finds it hard to move from her sofa. But her pale blue eyes alight with interest when I she knows I have gossip to share. 

“They were American,” I say. “Tourists. I could tell by their accents. Anyway, no one said anything. And it’s 2020. There have to be out gay people here now.”

“There are gay people,” she says. “But they live very discrete lives. Otherwise, they leave. Suzie’s step-son won’t come back from Miami. He doesn’t feel comfortable, doesn’t feel accepted.” She rubs her hands together, is as excited to say gossip as she is to hear it. 


“You should think about living in Grand Cayman full-time,” says my grandmother. “I enjoy having you here.”

We are sitting on the terrace of the hotel she manages. She’s sipping a glass of chardonnay with ice (the ice is necessary, otherwise the humidity would spoil the wine). I’m drinking diet coke. 

“You have the Caribbean in your blood,” she says. “And there are benefits to living on a small island. You can be someone, stand out. Canada is so big. It’s a sea of faces where everyone blends together. Plus, it’s so cold up there. Don’t you find it beautiful down here?”

Beautiful, yes. My grandmother’s hotel is in a remote corner of the island. It’s far from Seven Mile Beach, the main tourist drag with its huge stucco hotels, bumper-to-bumper traffic, KFCs and Burger Kings. Other than the roosters waking us up every morning, her property is quiet, surrounded by little more than sand, ocean and outcroppings of jagged rocks. Guests stay in quaint white cottages that fan out around gardens of tea roses, fuchsia bougainvillea. 

My grandmother and I live in a manager’s residence on the edge of the property, eat our meals in the hotel’s open-air dining room overlooking the Caribbean Sea. The adjoining bar is made from old bits of coral, has a thatched palm roof and is encircled by the terrace where we are sitting. Hammocks sway in the breeze.

“There are benefits to blending in,” I say. “I’m not sure I want to stand out.” 


Often, my grandmother and I have dinner and cocktails with other hotel guests. 

“I first moved to the Cayman Islands from Jamaica in the 1970s,” she says to a couple of sunburnt snowbirds. “Back then, there was nothing here but mosquitos. And I had to fly to Miami to get a decent meal. There wasn’t even good food in my hotel. My chef would serve empty snail shells and call that escargot. Just shells in butter!” 

“Your grandmother is quite a character,” says a British flight attendant, leaning in, chin on palms, hoping to hear more of my grandmother’s stories. 

“Matthew here is studying to be an architect,” says my grandmother, as my face burns red and I wish I drank alcohol, have something stronger than diet coke. I can’t. headaches. “He’s very talented.” 


“Granny, you can’t tell people I’m talented,” I say later as we’re walking back to our room, crickets chirping in the dark. “It’s not true. There are many people with more talent than me.” 

“Relax,” she says. “You shouldn’t be so embarrassed. We’re all just having fun here.” 

“Well if those people ever saw my portfolio they’d realize you lied to them,” I say.

“Oh who cares what they think,” she says. “Loosen up. In a hundred years we’ll all be dead and none of this will matter.”



Sometimes, I slip away from my grandmother, leaving her chatting with the guests, and sneak into her office, a room cluttered with hotel brochures, postcards, old invoices. I use her phone, a clunky old machine that also sends faxes, and call my boyfriend back in Canada. I’m being selfish, deceptive. I didn’t care about how Mr. Smatt, the hotel’s Jamaican owner, has to pay for hours of long-distance calls. No one knows that my boyfriend exists, that his name is also Matthew. 

“How’s it going?” Matthew says. 

“Not good,” I say. “I’m really lonely.” 

“Have you been out scuba diving?”

“A bit,” I say. “I saw a reef shark on Sunday. I didn’t know what it was at first. Then I was like damn, that’s a shark. It was freaky.” 

“Sounds like you’re having fun,” he says. 

“I’m not not having fun. But I have no real friends to talk to. Plus, I’m getting fat from eating all this hotel food, all the jerk chicken and rice and peas.”

“Yeah, sounds rough.” 

“It’s just, well, I don’t see anyone around here who looks like me, like us.”


“If you’re lonely,” says my grandmother, “why don’t you hang out with some of the boys who run the water sports?” She’s referring to a group of South African men who have come to Grand Cayman on a gap year between high school and university. They drive tourists around in zebra-print Jeeps and jet boats.

“I’m not sure we have a lot in common,” I say. 

“Nonsense,” she says. “But try to look smart.” She’s always outfitted in elegant dresses with her white hair quaffed. She clucks disapprovingly every time she sees me in shorts. “People down here like to dress up.” 


I put on long khaki pants and a blue dress shirt — ridiculous at the bar where I meet the South Africans, a rundown rum shack on Seven Mile Beach. 

“Mr. Smatt, what a dick,” says one of the South Africans, a young guy with messy brown hair. 

“Total bastard,” says another, in a t-shirt. 

“He’s so cheap, always stiffing us out of money,” says another smoking a cigarette.

They turn and stare at me as I silently sit in the sand, cross-legged, sipping a diet coke. 

“What do you think of him?” asks the one with the messy hair. 

“I’ve known him my whole life,” I say. “I can’t say anything bad about him. He’s let me stay in his hotels many times. Like right now.” 

“Sorry, who are you again?” asks the one in the t-shirt.

“I’m Pamela’s grandson. The hotel manager’s grandson.” 

“You have a girlfriend back home, Pamela’s grandson?”


“No, didn’t think so.” 

As the guys chug their beers, looking for girls to chat with, I sneak off down the beach, praying to never see them again. Which is of course impossible. They work where I live. But I can still hope.


“This cruise business is ridiculous,” says the architect I’m working for. “It shouldn’t matter if people are gay. I hope you know that.” 

He’s talking about a gay cruise that’s planning to visit Grand Cayman in a few weeks. It’s the first gay cruise to attempt a visit since 1998, a visit that never happened because the government intervened. There’s no injunction planned for the new boat, but many islanders say they will protest. Common fears persist: the gays will bring AIDS, destroy things, be perverts, offend god. A Cayman news show interviews a local who says “man is made for a woman, not for a man. It’s that simple.” 

“I know,” I say to my boss. “I know.”

My boss is a soft-spoken, gentle, unmarried man who’s always wearing crisp white shirts. He has no girlfriend and a way of moving his hands that makes me wonder if he is gay himself. He once talked about a male roommate. But of course he can’t, won’t say. How would anyone trust him to design a building if they knew he had ever had a penis in his mouth?


I’m at the hotel, in my bedroom, lying on my belly, writing an e-mail home to my family, CC’ing my grandmother even though she’s either in the room next door or down at the bar. I’m upset about the reaction to the cruise, I write. Why is the Caribbean so homophobic? I’m upset because I myself am gay. I tell everyone for the first time. 


I sneak into my grandmother’s office again. 

“I came out to my family,” I say to Matthew. 

“Wow,” he says. “What happened?”

“My dad said he didn’t care, my grandmother said she knew ever since I was born, my mom said the same but also cried and cried and cried.” 

“I’m proud of you.”

“Hopefully, this makes your visit a bit easier in a few weeks. Now I can tell my grandmother you exist, you are coming.” 

“I can’t wait to squeeze you again.” 


“You look like a woman,” a man tells me at Seven Mile Beach near my favourite snorkelling spot. I’m with Matthew, showing him around the island, the places I’ve been visiting since I was a small child, since long before I knew the words gay, homophobic. “The way you hold your hands on your hips like that. It’s not right.”

“What did that man say to you?” says Matthew. 

“Nothing,” I say, adding that although we’re at the beach together, we can’t hold hands, kiss, cuddle. It is advice my grandmother has given me, after telling me she “can’t wait to meet Matthew.” She says: “Grand Cayman is very conservative. You won’t see straight people doing those kinds of things either. Public displays of affection are taboo.” 

“It’s really beautiful here,” says my boyfriend. 

“It’s beautiful, but I can’t relax.” 


For years, I stay away from Grand Cayman. My grandmother retires, moves out of the hotel, downsizes from a townhouse, buys the yellow condo. Mr. Smatt sells the hotel. Whoever buys it runs out of money so has to sell the property to someone else who inexplicably tears it all down. That person runs out of money, too. The hotel is just rubble now. Things change. I finish architecture school, Matthew and I get married, settle in Toronto. We try to only visit gay-friendly countries until my mom says: “Your grandmother is getting old. You might want to visit her in Cayman while you still can.”

“It’s just, I hate spending my money going where I’m not wanted,” I say, but buy tickets regardless.


“I think things are actually getting a little better here for gay people,” I say to my grandmother in her condo. “Do you remember when I lived with you down here, at the hotel, and that gay cruise docked on the island?” 

“Can you pour me a glass of wine?” she said. “Chardonnay, with ice?”

  “Yes, granny.” 

“Anyway, yes, that cruise! What a fuss people made. All those people protesting down in George Town Harbor, quoting the bible, as though the bible tells us to hate one another.”

“The thing is, the island almost legalized gay marriage last year. And I just found a website called Colours Cayman that lists gay-friendly businesses. There aren’t many, but the list just started six months ago.”

“Which businesses?”

“Sunset House. It’s the only bar.”

“I always liked Sunset House.” 

“Matthew and I are going for drinks tonight.” 

“Sunset House is where I used to go when I needed a night off from the hotel. It’s near the airport. As planes would fly overhead, I’d always wonder: who’s about to arrive?”


My husband and I are sitting at the bar at Sunset House, overlooking the Caribbean Sea. The bas has a thatched roof, like my grandmother’s old hotel. I’m wearing a pink dress shirt, neatly ironed, with a pair of jean shorts, rolled up to my thighs. 

All around us, locals, tourists, all kinds are babbling away. A group of old men is playing checkers, surrounded by bottles of beer. There’s a mix of dress shirts and tank tops.

“Can you imagine doing this when you lived here before?” Matthew asks, sipping a Pina Colada, cream tinged brown with rum. “Us, out on a date.”

“No,” I say, drinking my club soda, casting my eyes about. For a moment I touch his hand. No one is paying any attention to what we’re doing or saying. I exhale, relax, smile. We’re anonymous, enjoying. 

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