Chris Holck, my parents’ pastor, has a lot of ideas about reaching retired baby boomers. But one piece of advice is at the top of his list: Don’t call it seniors’ ministry. They might be over 65, but boomers think seniors means their parents, not themselves. While you’re at it, he suggests, don’t call them retirees, either. (He prefers the “encore generation.”)

Holck knows of what he speaks—he’s both a boomer and the pastor of Live Oaks Community Church in The Villages, Florida, where most residents must be 55 or older. The congregation—whose motto is “Play hard! Pray hard! Finish well!”—is only slightly less eccentric than the famously eccentric city. One of the church’s biggest draws is its golf cart service, a “drive-in outdoor worship experience.” Yes, it’s a throwback to Robert Schuller’s drive-in church of the 1950s. Then again, it seems like everything in The Villages is a 1950s throwback. Holck says boomers often struggle through a “middlescence” looking for meaning—a second adolescence as restless as the first. Indeed, driving past parking lots full of baton twirlers, tribute bands, and classic car collectors, it’s clear that many in The Villages are spending their second adolescence replaying their first.

That kind of weird denial is intentionally and literally stamped into the core of The Villages: Plaques throughout the town squares describe old buildings, personalities, and events that never existed. A boat tour offers a town history more fictional than Disney World’s Jungle Cruise. My folks and the other 125,000 residents are all in on the joke, thinking it’s both weird ...

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