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Home Lifestyle

Italy Broke My Heart—Ten Years Later, I Went Back

September 23, 2025
in Lifestyle
0
Condé Nast Traveler


Ten years ago, I left Italy with a suitcase full of olive oil and tears streaming down my face, and vowed never to return.

It was about a boy. A Roman boy, for whom I’d moved to Italy and had lived with for two rocky years. It was not a good relationship, and I was not my best self in it; something about existing entirely in his world, identifying as a full-time stranger, made me feel weak and destabilized. Though I kept telling myself this was what I wanted. In retrospect, I liked the optics of us, two reckless artists in lust, more than the reality: a 35-year old woman dying to settle down and have kids, and, as I saw it, a man-child who only cared about himself.

The worst part was, it was he who broke up with me, on top of the Spanish Steps no less, declaring he wanted to be alone and no longer believed in love. It was brutal. Saddest of all, it ruined my love affair with Italy, where for two years I’d ridden my vintage bicycle from market to market, napped on tapestries at Lago Martignano, and actually gotten paid as a writer to pick caper berries in Pantelleria or shop for porcelain ashtrays at the Ferragamo Museum.

Before running home to New York—sad, embarrassed, defeated, a wreck—I had an assignment to complete. I was supposed to write about Borgo Egnazia in Puglia, the luxurious seaside hotel that has been attracting celebrities and other beautiful people since 2010. I’ve never missed a deadline in my life, but after taking an hour-long flight from Rome down to Bari, there I was, soaked in Negronis, weeping in the piazza, sobbing by the bougainvillea, and hysterical in their hamman. On my second night, I was scheduled to take a private Puglian dance lesson, but I physically couldn’t kick or twirl. My limbs were utterly devoid of spirit. Ultimately, I emailed my editor saying that I had a personal emergency, and had to bail on the assignment to go home early. Before I left, I took a moment to pray (literally pray!) on the rooftop of my casetta, my eyes piercing the periwinkle sky, that one day I’d return to this hotel—but as a proud mother.

The Spanish Steps in Rome, where the writer’s first Italian love story ended.

Nico De Pasquale Photography/Getty

Ten years after the breakup, writer Alyssa Shelasky plans an Italian vacation.

Alyssa Shelasky

After Italy, I wisely decided to quit men and have a baby on my own. One year later, I gave birth to my darling daughter, Hazel. When Hazel was 6-months old, I accidentally fell in love with a documentary filmmaker, Sam, who eventually adopted her, and then we had another baby together, my son River. Now we’re a joyful family of four, living on top of each other in Brooklyn Heights, renovating a house Upstate, embarrassingly happy.

There’s just one issue: Sam, Hazel, and River are Italophiles. Before meeting us, Sam filmed a food series in Trieste that left him wanting more; Hazel takes Italian at an after-school program; and River, our yummy 5-year old roughneck, is aptly nicknamed Tony Soprano. All to say, ten years after my hellish heartbreak, I felt compelled to take them to the country I’d previously shut the door on.

Tags: personal essays
Editorial Team

Editorial Team

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