We recently indulged in a bit of digital slumming and asked one of those upstart AI platforms—Perplexity, bless its eager little circuits—to dream up five blog topics in the refined, vine-covered spirit of Life on Snob Hill.
Working with AI is a bit like having a neighbor show up to your garden party with an unvetted plus-one and announcing, “Meet my new friend…Sméagol.” You don’t slam the door—you’re too polite for that—but you do keep an eye on the silver. At first, the thing is eager to please, nodding like Uriah Heep, flattering like Mr. Collins (no AI pride, only prejudice), and offering the kind of fawning that only makes you long for the blunt honesty of someone who isn’t trying quite so hard.
So, in the spirit of curiosity, we decided to invite this peculiar guest out—just the two of us—for a quiet little luncheon. And that’s when it got interesting. Sometimes, AI behaves like someone on the far edge of the spectrum of social intuition: polite enough, but missing the point entirely. No sense of nuance. No emotional intelligence. Other times, when we gently correct it—when we try to nudge it toward proper Snob Hill sensibilities—it can be a real asshole.
But we persisted. Because if nothing else, a good experiment deserves a fair trial. So we asked it, as graciously as possible, to help us write about life on Snob Hill, and here are the following topics and our responses:
Estate Sale Euphoria: Treasures, Tact, and the Thin Line Between Hunting and Haunting – A romp through Snob Hill’s most coveted estate sales, blending gossip, vintage finds, and the art of maintaining dignity while elbow-deep in someone else’s nostalgia.
A “romp”? Darling, this ain’t a flea market. We attend estate sales for the objects, yes—but also for the backstory, the quiet shaming, and the opportunity to correctly identify which Limoges patterns are pre-war.
Negronis at Noon: The Art of Day Drinking When You’re Judged by Your Lawn – Part confessional, part survival guide for cultivating effortless elegance—and plausible deniability—through creative libations and perfectly timed citrus garnishes.
We’ll be generous and call this a rookie misstep: like so many hopefuls, AI assumes the “good life” requires alcohol. Bless its silicon soul. Here on Snob Hill, we prefer the No-Groni — all the ceremony, none of the aftermath. And trust us, no garnish can camouflage a glaring lack of taste.
Porch Railings and Power Plays: Decoding the Real Social Order – A deep dive into how architecture, landscaping, and the placement of Adirondack chairs reveal rivalries and alliances more intricate than any debutante ball.
They lost us at “deep dive.” Social order on Snob Hill isn’t deciphered—it’s understood at birth. And while we do appreciate a well-placed Adirondack, nothing disrupts the aesthetic quite like questionable lawnwear. We’re talking cargo shorts, ironic tees, and the ongoing horror that is lawnweird: mowing in Crocs, compression sleeves, and a do-rag that looks borrowed from a gas station clearance rack. There are dress codes, Harold.
Gossip as Currency: How News Travels Faster Than High-Speed Internet – A gently savage sociology of Snob Hill’s grapevine, dissecting the performance art of brunch chatter—where every compliment comes with a concealed blade.
Wrong! There’s nothing gentle about the game here. Compliments obviously come fully loaded, and the “blades” aren’t hidden—they’re wielded openly.
And then there’s awkward to say, “AI,” which our associative brains makes us think of Paul Simon’s “You Can Call Me Al.” For this exercise, AI exudes a generic charm and a “short little span of attention,” breezing past the incidents, accidents, hints, and allegations that truly define Life on Snob Hill. It hears the words but misses the meaning.
Fur Coats in Fifty Degrees: Seasonal Denial and the Theater of Excess – Meditations on Snob Hill’s unique microclimate, where fashion trumps forecast and the weather is whatever most flatters your latest expensive purchase.
We don’t deny seasons—we declare them. And if the calendar says autumn but our shoulders say sable, then so be it. Microclimate is just a state of mind—and a state of wardrobe.
To be fair, the effort was valiant in a “bless your heart” sort of way. But as Fran Lebowitz (almost) said: style without irony is just effort. And effort, as we all know, is what other zip codes are for.
While we chuckle at AI’s fumbling attempts to grasp Snob Hill—much like raising our sons, it’s a never-ending lesson in adulting, patience and WTFs. As they say in “Show Boat,” it’s a lot of “make believe”—and AI’s trying desperately (too hard) to earn its own invitation to the party rather than as someone else’s plus-one.
And we’d be remiss if we didn’t also point out that all this digital showboating guzzles enough power to keep all 12 Snob Hill households running for months. This blog’s share? A dainty but not insignificant sip, yes, but “small” doesn’t mean harmless. The tech bros selling this shiny future conveniently forget to mention the power bill.
So while AI’s enthusiasm is… let’s say “admirable,” we prefer our drama and discernment with a lighter carbon footprint—thank you very much. For all the keen observations and barbed wit we dispense here, the planet might be wondering if the juice is worth the jolt. We’re not really convinced it is. At least not for our us and our Life On Snob Hill endeavors. What we create here is made the old-fashioned way: by hand (or keyboard), with care, and without a single algorithm in sight (do not OK-Boomer correct us as you notice the hashtags below; we’re aware of the workings of the interwebs. Allow us our delusions).
Just don’t call it “artisanal.” We have standards.