The Villages Killed My Florida Dream

Recently I dreamed I was in a public park. The grass was cartoonishly green, a kind of chlorophyll utopia, and families sprawled across it like they’d been carefully arranged for a Chamber of Commerce brochure. My suitcase sat at my side like a misplaced airport refugee, and then I looked up.

Looming above the park was a billboard—a monstrosity of sun-bleached cheer—featuring a leathery couple in their seventies. They were bronzed like overcooked turkeys, grinning wide, basking in the eternal glow of some Florida condo where “Margaritaville” played on an endless loop. This was not their first rodeo: it was their fifth marriage each, the residue of decades spent riding the carousel of lust, liquor, and litigation. Their message was plastered across the sky: hedonism may lead to divorce court, bankruptcy, and sun-damaged skin, but look—if you just keep grinning, it’s practically a lifestyle brand.

I felt an almost religious revulsion at the billboard. It was hollow cheer dressed up as wisdom, a glossy ad for despair masquerading as joie de vivre. Pulling my luggage closer, I glanced at my watch and felt relief that my wife and daughters would be joining me soon. The counterfeit joy overhead only made me hunger more for the real life that I have.

The “Margaritaville” billboard—two geriatric smiles frozen in sunlit rapture—reminded me I’d been meaning to watch Some Kind of Heaven, the documentary about The Villages, that gargantuan playground-for-the-aged about forty-five miles from Orlando. If synchronized water ballet to Neil Sedaka and margarita-fueled Parrothead parties sounds like paradise, The Villages will sell you heaven with a tiki umbrella on top. For anyone with taste, patience, or shame, it reads more like an early-onset hell: a tropical gulag where you pay staff to micromanage your leisure until even leisure looks like a job interview.

The film’s most magnetic human mess is Dennis Dean—an eighty-one-year-old small-time grifter wanted for a DUI in California, living out of a blue van on the edge of The Villages and scheming his way into the bed of a rich widow. He prowls bingo halls and church socials with the persistence of a con man who’s practiced charm until it’s fossilized. When police finally close in, Dennis slips back into Nancy’s apartment and in a scene that sticks with you he lies on her bed while she calls from the kitchen: “Lunch!” He doesn’t move. He stares at the ceiling fan as if it’s a slow, merciless clock—and you can see, plain as day, that comfort can be prison for someone whose last liberty was earned by deceit.

The director never sneers at the subjects. Pain and longing are shown with a kind of blunt respect. But the portrait of The Villages itself isn’t charitable: it’s a retirement complex caught mid-regression, a carnival mirror that reflects geriatrics clinging to perpetual adolescence until the spectacle curdles into something queasy and cringe-worthy. The architecture of fun—shuffleboard courts, themed parties, and scheduled joy—becomes a machine that demands you perform your own amusement. It’s not freedom; it’s occupation by leisure.

And yes, I realized, sitting there with my pride intact and my Florida fantasies suddenly damp, that watching this must have been my wife’s brilliant little psy-ops. For a year I’d been nagging her about moving the family to Florida—stilt houses, salt air, a hammock with my name on it. Some Kind of Heaven demolished the fantasy with water ballet and sedated margaritas. The obsession evaporated. Apparently, all it took was Neil Sedaka and a ceiling-fan stare.

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