Oppenheim follows these people for a bit of their lives. Inevitably, they become more than the stereotypes we expect them to be. They become sympathetic, even.
Anna’s eyes glass over when Reggie comes home, fails to acknowledge their anniversary, then asks her to leave him alone while he goes in the other room to meditate and “jack off”; she confides in a friend that she’s torn between breaking the marriage or sticking with the guy.
Barbara meets a genial fella, a golf cart salesman known as the Margarita Man; they have a great time playing mini-golf together, but she looks crestfallen when she attends a Parrothead party and he shows interest in other women. Dennis reveals that he’s got an arrest warrant for a DUI in California, and he’s broke, and he’s calling people and hustling them for money and guilting them by threatening to kill himself; he seems increasingly pathetic and forlorn, gets help from the preacher, finds an old girlfriend and moves in and waits until she’s gone and lights a cigar in the house and then walks around spraying air freshener. Another day in the paradise of The Villages.
A woman directs a line of golf carts into an elaborately choreographed display. A boatful of senior citizens paddles in sync under the direction of a coach. A group of women coordinates a synchronized swimming machine. In voiceover, a man talks about how great The Villages community is; it has no slums or children, and “You don’t have to socialize outside the villages,” he says. We see images of pools and pickleball courts, nightclubs with dance floors and live bands, groups of bellydancers gyrating to Christmas carols, supermarkets and shops, bustling sidewalks and restaurant patios, a club consisting entirely of women named Elaine, a church service with a loud preacher on a stage populated with crazy mannequins. It’s a boomer bubble, and very, very Caucasian. The son of The Villages’ founder calls it “Disneyland for retirees.” A crazy-eyed citizen calls it “nirvana.” It’s not a gated community, a gate-booth worker says, but a “community with gates.” These are all public roads, you see. Gotcha on a technicality there!
We meet the main players in the movie, residents of this pre-Heaven suburgatory of people who chase their youth in the twilights of their lives. Anna and Reggie have been married for 47 years, but it’s not rosy; he gripes that she’s too committed to her athletic activities, but she’s been putting up with the eccentricities inherent in his quasi-spiritual explorations inspired by his regular drug use, which leads to his arrest and subsequent legal trouble. Barbara is a Boston export, recently widowed, lonely and surely still mourning; she participates in an acting workshop, tambourine lessons and singles mixers, hoping to maybe find a partner. Dennis doesn’t live in The Villages, but rather, in his van in a parking lot in The Villages, when he doesn’t get chased off; he says he wants to land a wealthy woman and has any number of qualifications for said woman’s manner and looks, despite not being much of a catch himself, considering he’s got many hallmarks of a serial fibber and con artist.