KEYS DATING SUCCESSES AND CAR CRASHES AS TOLD BY LOCALS

Angela is a 50-year-old divorcee in Key West who hasn’t been on a date in two years. And she’s just fine with that, thank you very much.

“I live a nice, peaceful life,” the business owner told Keys Weekly. “I’m a really good solo act. I don’t yearn for a partner.”

But it also doesn’t help that the last man she dated had more red flags than a marching band.

“The first date [in Cudjoe] was a fiasco. He got inebriated,” she recalled. “I thought, ‘I can’t let this guy ride his motorcycle home.’ He agreed to let me drive him. But he couldn’t remember where he lived. Then he tells me he was going to walk back to Cudjoe to get his motorcycle, so I drove him back to Cudjoe. He said he didn’t have his keys, and he starts ransacking my work van.”

For another date, they agreed to meet up at her home to start the night. When he arrived, he immediately asked if he could take a nap. “I went out, and when I came home he was still asleep. I got a text from a friend asking me to go out. I couldn’t wake him up, so I went to meet my friend. When I came home, he was gone. That was a couple of years ago, and that was my last real date.”

Angela’s story was just one of the doozies about dating that Keys Weekly has heard in response to a post we wrote on a community Facebook page with 24,000 members. Seeing as how Valentine’s Day is just a few days away, we had been thinking: What’s it like to be single and dating in the Keys right now? And how has the pandemic affected the single life?

Dawn McCurdy-Cale and her husband Ed Cale in 2019. CONTRIBUTED

We asked locals these questions in our post. About 40 commenters, most of them female, left 120 comments, and our DMs blew up, full of people who wanted to share their tales, including Angela’s, above. And hers was one that was tame enough to print.

Locals kept repeating two popular sayings about Keys dating. The first one? As one young Upper Keys single gentleman wrote, “In the Keys you don’t lose your girl, you just lose your turn.” 

In other words, it’s slim pickings out there.

“Everyone is related somehow, so better pick which family member you want lmao (I am joking but it’s kinda true),” wrote one young single female.

“A breakup in 2017 caused me to LEAVE the Keys,” commented another female. “While housing, location, and other issues affected the move, a HUGE issue was the lack of a viable dating pool. Desirable, fit, stable, youthful men in the 55 to 65 range are pretty much non-existent in the Fla-Keys.”

Katie Lou and Adiel Ramirez in a recent photo. CONTRIBUTED

Thirty-year-old Samantha Dellilo first met her fiance at Key Largo School when they were age 9. “When I go on a jog in my neighborhood, I see three ex-boyfriends,” she told us on the phone, half-jokingly.

Jesse Hayes, 37, is a single Islamorada commercial fisherman. “A s****y aspect of a small town is when you have (a relationship) go sideways, you go to the Trading Post to get chocolate milk, and you have to say hi,” he said in his interview.

Speaking of going “sideways,” it appears that many Keys relationships frequently do, thanks to unstable behavior. Enter the second saying that local daters often say to each other: “You have to import the good ones.”

“The bar is so low here,” said Angela, who dated the inebriated motorcycle guy. “I know a lot of people in relationships here, and I wonder if their behavior would be acceptable on the mainland.”

“I think the Keys has a culture based on fishing and drinking and, those two things, when you put them together, the kind of people that that draws, I don’t think they are gonna be paragons of responsibility,” said fisherman Hayes, pointing out that it’s not just men who are unstable. “I don’t want to be disrespectful, but a lot of (women here) are emotionally unstable. I’m not looking down on women — that’s not where I’m going with that at all. Everyone has things to work on. But it is a sh*t show here.”

Samantha Dellilo and fiance Marky Berta. CONTRIBUTED

Throw in the pandemic, and you have a mess. “I spend more time with lobsters than women,” Hayes joked. “(Dating is) nonexistent. I mean, what do you do? Get on f*****g tinder, the sh*t show Olympics? And then what? You end up having a text conversation and you never meet up? It’s an exercise in futility.”

But we heard lots of positive stories too. For example, not just one, but four different women commented to say that they met their husbands at Key Largo’s Sharkey’s Sharkbite Grill, a.k.a. “The Tank.” And Upper Keys poster Nikki Dunn Cullen met her husband at a kickball game. “My husband and I started dating thanks mostly to being on the same Founders Park kickball team the first season they held it. Our team won the championship and John won my heart!”

Dellilo’s story of meeting her fiance in elementary school would charm even the most jaded heart. When he walked into their fourth-grade classroom, “I hit my friend on the shoulder, and said, ‘Oh my god, he is a hunk.’ I was so smitten. We were friends for years. I was crazy about him, and everybody knew it,” she said.

Katie Lou Ramirez, 32, is a mother of two who met her husband, Adiel Ramirez, at her father’s workplace in the Keys. “I was single down here until I was 24,” she told us in an interview. “I was lucky to meet my husband because he was working for my father. He came from a good family from Mexico, and he came to the Keys not for girls but to make money for his family. He’s my soulmate. It’s crazy that it took someone coming from Mexico.” 

He charmed her when he and his brother dressed as Super Mario Bros. to impress her nephew. “After my nephew’s birthday party, Adiel went to my dad and asked permission to ask me for a date. And we’ve been together ever since.”

Dawn McCurdy-Cale met her husband of 30 years at the Safari Lounge in 1987. Her advice? “Don’t give up hope. And try searching for companionship before searching for romance,” she told us in a DM.

We contacted Melinda Van Fleet, a success coach and a Keys Weekly columnist, for more guidance. “When looking for love, it’s important to be aware of yourself in conjunction with your expectations,” she told us. “Often, we have things we have to work on first. And doing that work is important.”

We also asked Tavernier relationship and family counselor Diane Saleeby Gardner for her thoughts. “Expanding and thinking outside the box can be exciting. Joining groups such as book clubs or other interest groups could bring not only different people but include common interests that bond people in deeper ways. You could also find an international group that expands your world views. There are pros and cons in dating during Covid, but it gives one the opportunity to do something different. You may end up finding the partner of your dreams.”

And we all need to remember that we are fortunate to live in paradise. 

Christopher Massicotte, 45, told us, “I met my fiance in a hotel bar in Orlando, on March 6, just before lockdown. He is a flight attendant for American and was on a layover, and I was there for work. I invited him to come visit, and he never left. Nine months later, we were engaged. I proposed to him at the Dry Tortugas. But if it wasn’t for Key West, we wouldn’t be together. Someone asked him if I’d said, ‘I live in Columbus, Ohio,’ would he have come to visit, and he said, ‘Probably not.’”

*Some names have been changed to protect identities … and give them a fighting chance at another date one day.

Charlotte Twine fled her New York City corporate publishing life and happily moved to the Keys six years ago. She has written for Travel + Leisure, Allure, and Offshore magazines; Elle.com; and the Florida Keys Free Press. She loves her two elderly Pomeranians, writing stories that uplift and inspire, making children laugh, the color pink, tattoos, Johnny Cash, and her husband. Though not necessarily in that order.