The Ex-Mrs. Hedgefund

As the plane started to descend on the Old World, I was glued to the window, drinking in the different topography and totally new visual flavor. Sometimes, to get out of a rut, you have to fly out, via 777. It was like my passport stamp was a defibrillator jolting me awake after a haze of zombie-like existence as opposed to living. The little rooftops were centuries older than anything at home, and suddenly the U.S. felt like strip mall central next to the rustic charms of Italy. You could highlight and drag one seminice building from Europe and paste it into New York and it would be an insta-landmark. But we had our own brand of magic buildings at home, and while I was thrilled to be abroad, part of me missed the glimmering Gotham skyline already.

To say that it made a monk’s quarters look like a baronial spread would not be an exaggeration. So much for the appealing virtual tour online. The room must’ve been like eight by nine feet, with a tiny doll’s bed in the corner, a small drawer set, and a bathroom where the showerhead is above the toilet so you can pee and condition your hair at the same time. There was a tiny Shawshank Redemption-style window about the size of a Scrabble board and a framed map of the città. Okay, I thought, the plan is not to spend much time in the hotel, anyway.

So I meandered out to achieve my first order of business: gelato. I glanced in the glass-covered bins of two places before I knew I’d struck gold; the coffee gelato in the third joint was so dark, it looked like espresso. Never had I tasted anything so orgasmic. The flavor on my dime-sized spoon could kick the ass of a pint of any coffee in the States. Bliss.

With my dish in hand and bag slung over my back, I trolled the little winding streets, marveled at every church I stepped into, and crossed the Ponte Vecchio to scope out the view of the river. The freezing wind was blowing through my hair and I leaned over the wall to look at the other side of the city and felt so proud of myself that I had come here alone. After years of Black Falcon Club trips with Tim, this felt way more adventurous. I had a small fear that I could be abducted and no one would ever know or remember seeing me, but for some reason I felt braver than I did at home, and my ignorance of bad neighborhoods in Florence sent me exploring for hours in every dark corner. I’d never dawdle aimlessly in twisting gray streets at home, but I was so curious about the random fountain at the end of a stone path, or the hidden palatial town house or a tucked-away mosaic. The sky fell to electric blue, then darker purple, and the stones beneath my feet looked almost shellacked black, like perfect skipping stones but big. An old woman out of central casting was attending to her window box and I decided to walk back through the dim-lit streets, and change before taking myself out to dinner.

I was lured off the non-tourist-trodden path toward a small cove aglow with the orangey flicker of a fun little hole-in-the-wall café. The place must have had a total of thirteen tables, and there was loud music, big plates of food, and happy, dolce far niente, life-loving eaters. The one drawback was the gust of smoke, but hey, I was in Italia, so I smiled at the guy who seemed to be in charge. He came over and I did the universal sign for I am a loser and need a table just for me ’cause I am totally alone in the world (the index finger up as if to say one, please). I got a look of pity and even saw him exchange glances with one of his amici, but he sat me in a very cute minitable in the corner.

“Studiava all’università.” First they angled their chairs toward me, then a cute couple walked in and knew them, so they introduced us. The woman had vibrant blue eyes and jet-black hair and the kind of weathered gorgeosity and extreme facial architecture that women find beautiful; guys don’t always agree. We all hung out and they told me places to go, and even gave me their mobile phone numbers. I loved disposable friends. They were like my new best buds, kissing me good night and offering rooms in their homes, and I could be an effing serial killer. Fascinating. In New York, people would probably just whisper and feel sorry for me, and in Italy, they pull up chairs.

The next day I wandered to the Uffizi and waited in an endless line to get to Botticelli’s Primavera, which was sadly behind some bulletproof glass, which I found odd-slash-annoying. Some maniac had attempted to slash it. Who are these people? I camped in front and just zoned out staring at the fabrics of the maidens’ dancing gowns, hypnotized by the ethereal gauzy haze. The women looked so serene, lost in a milky swell of lightness. And soon I felt as light as spring as well, renewed and fresh.

Seeing the painting, more because it was famous and reproduced everywhere than because I loved it, was like seeing an old friend. Way beyond a familiar face, the works in the galleries were like lost close childhood pals rediscovered on foreign soil. And because I was a lone American woman, these were connections not only to home but also to my past.

I passed an Assumption into Heaven, in which a weightless Christ with luminous skin was making his way to the sky. I saw Titians with blue so saturated and choked with color that it was as if the artist had ground up stones and spread liquid lapis on the panel. Staring at these masterpieces, in delizioso Italia, I felt poetic, romantic, with the excited chills that I normally reserved for a movie’s final sunset-dappled kiss.

The next day I went to see the giant statue of David, and in the massive hall, there were a hundred studenti hanging out. It was funny to see a European cultural icon being treated as some ho-hum regular backdrop, but Miles and his friends often played in the Temple of Dendur at the Met in the winter, throwing pennies, laughing as if they were on a jungle gym, oblivious to the treasures perched among their sneakered feet. If you live with it every day, it may lose its luster. Still, I always loved walking in that looming glass room whose stark interior bled into Central Park’s resplendent trees, and I never took it for granted.

His name was Marcello and he was a former art student, now a lawyer, who had grown up in Bologna and moved to Florence a few years before with his firm. I marveled at the other great drawings on the layered pages of his pad, and he asked if I wanted to have lunch. He was handsome in a really foreign, dark way, and we talked about America and art and my trip and ultimately, why I was taking it.

We never got to that point, obviously, but walking with Marcello I felt unedited and I talked forever about Miles, and then Tim, popping the cork on my emotional Prosecco. We walked through the little streets and watched the sky fall dark, and he asked if I wanted to come over.

In retrospect, I realize I must’ve been on crack to just follow him up the three flights, but for some reason it felt like a good idea. The alternative was being alone again, and I was suddenly not into that. We entered his apartment, which I thought for some reason would be a cyclone-hit mess, but it was surprisingly cute and clean, with huge arched windows overlooking a square and a little painter’s corner with pots of brushes and an easel. After he closed the door I got that weird rush of being in a total stranger’s abode. What was I thinking? He could be Gioffreddo Dahmer! Maybe he’d hack me up and make paint out of my blood and guts, Red Violin-style, and brush me onto a canvas.

He brought me some bubbly water, smiled, and plopped down on the couch. What if it was drugged or rufy spiked? It’s poison! It was from a glass bottle, Holly. Okay, okay, he’s fine. Not Teodoro Bundy. I was being paranoid, I realized, and calmed down a bit. But I apparently still was a little on edge, thinking of people saying, as I would, “She went up there to his place? Then she’s an idiot and it’s partly her fault she got raped and hacked to bits!”

Marcello, as it turned out, was not a razor-wielding rapist-murderer. Not Carlo Manson. He was a sweet, honest man who had just broken up with a girlfriend, and we ended up talking about life and relationships for a few hours. I tried to extract little pieces of wisdom from him, but it all mirrored what I already knew, just in slightly different words.

There was absolutely zero sexual tension. We shared only a mutual smile where we both knew we could have had a little bacio, but what was the point? It would just be a Band-Aid for two recovering lovelorn souls who were feeling a little small. How fitting that we had met next to a giant David, the underdog who later pulled through. Maybe we would, too . . . but not together.

When I arrived in enchanted Venice, it transcended my gargantuan memories. How many things are actually better than you imagined? I’ve heard people say it was smelly, that there are omnipresent rats, that it was a massive sewer. They all were wrong (then again, I was there in crisp October, not stinky July). Plus, I never saw one rat. Okay, I saw one, but it was swimming in the canal and my water taxi driver said, “Don’ta worry, they do notta eat the turisti.”

I got to my little hotel and immediately called Miles to tell him I missed and loved him. And while I could hear Avery’s voice in the background, which made me puke-ready, I took comfort in the fact that my son sounded happy. After we hung up, I unpacked and settled into my room, which was way better than the nun’s quarters in Florence—this time it was bellissima and my queen-size bed was actually long enough so that my cobblestone-weary feet didn’t hang off the end. The large single-pane window was crisply Windexed and much bigger, so the muted splish-splash of the narrow waterway outside could be heard all night, lulling me to sleep like I was in a giant womb. I walked everywhere in Venice, through the charcoal alleyways lined with creepy mask stores. Carnivale must be a really big deal there to sustain so many of them. As a rabid coulrophobe (victim of a paralyzingly traumatic fear of mimes, clowns, and worst of all, ventriloquist dummies), I had goose-bump-laced, violent reactions to the white, spooky, I-am-a-murderer visages.

The next day I walked to San Marco Square and bristled with a bad case of the skeeves when I saw the hordes of pigeons (i.e., rats with wings). But then I remembered a photo of my mother standing in the very same spot at age eighteen, smiling by the domed wonder of the basilica in front of me. I got a tear in my eye when I thought of her, and how the pain of missing her would never subside. I wished she were there to coach me through this year. But I would summon her strength, as I knew she would have wanted me to.

My final day pre-departure was spent on a gondola. I scanned the striped-shirted men and when a cute old guy smiled at me and called me bella, it was game over. I hopped in and was amazed at how he expertly maneuvered me through the tiny canals as if we were a duck. I leaned back in the love seat clearly meant for two and drank in the rooftops and filled clotheslines. Considering that this city in its aqua maze had always occupied such a hallowed place in my imagination, it felt like a miracle to absorb the reality of that moment. This soaring above my own dream gave me something I never expected: the realization that I was not jaded. Things would be fine. Because I was not wounded and scarred enough to be closed off to the details, the visual balms, that make everything feel healed inside. It was as if this trip had peeled off a few pieces of that emotional Scotch tape, and plucked out one or two staples holding my heart together. And as Mario burst into “O Sole Mio” when we crossed under a bridge, I got the rush of knowing my hope was restored. Of knowing some things are better than we dreamed when we book a spontaneous ticket online, and that the lapping water at the shiny boat’s side was a symbol that taking a risk can be this refreshing.