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.

How you know she’s Caroline Calloway and not