The Great Pretender

Caroline Calloway's first big "scam" was a lark. Her next, a matter of self-preservation. She's about to debut her latest project-or so she says

- By Lili Anolik. Photographs by Martin Schoeller

IT’S 10 A.M. on a Monday, early February, and I’m stepping off a plane in Sarasota, Florida. I’ve come to visit Caroline Calloway, scandalous internet celebrity. (“Scandalous internet celebrity” is what I’m tagging her with now because I have to tag her with something, and it’s accurate if inadequate. Tagging her properly is, you could say, the point of this entire piece.)

A short Uber ride takes me to a building that’s very clearly a retirement home though not explicitly billed as such. No one in the lobby or on the grounds is a day under 80. Lots of bright white sneakers and denim pantsuits. I hold the elevator for a woman with a walker who wants to show me the package she’s just received from QVC.

I exit the elevator and there’s Calloway, framed in the doorway of her condo, one foot forward, the other back. She’s 31 but looks like a girl, like Alice in Wonderland: small and slender with smooth, honey-hued skin; a precisely molded forehead, chin, and mouth; large, clear eyes. She has an armful of cat, stuffed, I think at first, only realizing my error when it slow-blinks at me before turning away in feline disdain. A ribbon ties back her long hair, brown, though somehow not, somehow giving the impression of fairness, blondness. Her clothes are plain yet stylish—oversized white oxford, fitted blue shorts, blue flats.