One of my most endearing and exasperating qualities is my un-jaded enthusiasm for vacation flings. I’ve started to view my holidays abroad as “expeditions,” ripe with soul-searchingly cerebral and intentionally romantic experiences. Basically, any hanky panky that happens along the way gets rebranded as an “anthropological examination of the local culture and flavor.” I’m a curious person. I love research. I love culture. I’m a whore for flavor.
I can get attached to a vacation fling pretty quickly. But I’m enough of a realist to know that this brand of romance is often a byproduct of all the best parts of vacation. Ephemerality. The lack of fixed schedules. Tripping on jet lag. Perfect weather. A newly-developed tan. One-too-many glasses of wine. Cute language barriers. Endless gelato. And a feigned fearlessness from tossing around basic-ass vacation-mantras like “when in Rome” or “carpe diem.” Despite my tendency to briefly fall in love with my vacation baes, I’ve gotten good at knowing what is really what. With most holiday hookups, the Whatsapp love letters tend to dwindle into infrequent upside down happy face emojis. And often I might not remember if bae’s name was “Andy” or “Anthony” or “Filippo.” Who the fuck was he again? Head scratch.
But last year, I let a VF turn into a kinda-really serious long-distance relationship. I did assess the risks; I calculated the time, money, and likelihood of heartbreak. And then I dove heart first.
The backstory: I was visiting Naples, Italy alone for a life detox. My dad had unexpectedly passed away two months before, and I was coping with the DNR order I had to make when the hospital confirmed dad was braindead from a subdural hematoma. Naples wasn’t on my list of places to see, but that’s precisely why I went. To defy all context. To breathe new air. To let myself be whisked away by the unknown. To eat pizza. Then I met Diego.
Unlike the movie tropes of fated run-ins, Diego (a born-and-raised Neapolitan) and I met on Tinder. Because I didn’t have any idea what I was supposed to see or do in the city, I used the dating app to crowdsource tips from locals. Of the fifteen locals I matched with, Diego was the first person who spoke English with native English-speaker fluency. And we both liked The Cure. Easy.
Of course, it’s not vacation romance without some logistical drama: We hesitated on meeting until the day before I had to return to New York. Our hang was squeezed in between a Covid test and frantic packing.
We met in the Vomero neighborhood, outside a pharmacy where I was getting the Covid test. Our quick drink turned into a few hours of roaming the city — rom com-esque whenever I’d adorably try to speak Italian, and Richard Linklater-esque when we’d trade notes on Bukowski, Nick Cave et al. Around hour four, we ended up at a park, knees touching on a bench, and watched everyone else watch us look super cute together.
“If only you had one more day left here,” he’d say throughout our date. “If only I lived here,” I cooed back. The call and response of “if onlys” and the palpable desperation for more time together made this first-date feel bigger than it was.
It ended up being a 13-hour date plus an hour of the frantic packing. Diego escorted me to the airport. He cried. (Honestly to this day, I’m still debating if that was sweet or a red flag.) He promised to fly me back to Italy, which he did. Then I flew to Italy again on my own airline miles. Then he visited me in New York, and spent Thanksgiving with me and my friends. He lived up to his Italian stereotype and wooed my pals with homemade tiramisu. Then I flew to Italy one more time because we were ready to look at apartments and consider starting a new life together…in Naples. That’s when things fell apart. We realized our relationship was a castle made of sand—and it was built on a toxic waste dump of cultural and personality incongruities. And it all came tumbling down over a fight about parking. Maybe it was the fight about the Airbnb. Or whether the mozzarella should go in the fridge. All it took was a sneeze, really.
The breakup happened in one those beautiful Italian piazzas in Milan. He broke up with me kindly, very “American-ly” by telling me that he didn’t think he could give me the love I deserved. Contrived breakup dialogue cuts deeper when said in an Italian accent for some reason.
You know that feeling after coming back from an epic holiday and knowing you have to go back to work? That’s how I felt the weeks after. Dreading “Monday at the office” and “lunch at my desk.” Except, dreading going back to being that single 37 year-old writer-or-something with no business planning a life in Italy, with my Italian housewife dreams dashed. But that’s how it always goes after breakups, vacation fling or not. Crushed hopes. Cocteau Twins. Blah blah. Then the process of healing begins as the vacation-tinted mirage wears off. The obvious issue was that we were soooo incompatible: Diego hated that I wore down jackets. I hated that he still lived with his parents. Diego hated ginger (I love ginger). I love to travel (he couldn’t afford to travel). It would have never worked. And yes, he probably couldn’t give me the love I deserve.
…and that was four months ago. I’m totally good now. And since then, I’ve actually completed another trip to Italy. This time I traversed Sicily from east to west for two weeks, and ended up in Rome for a brief layover. I haven’t spoken to Diego. Who the fuck was he again? Just kidding. However, I realized on this trip, my vacation romance with him opened up a portal to the real romance I was supposed to have, one that’s richer. It’s a budding romance between me, a courageous solo traveler, and Italy— a place where I can see myself living some day. Yes, I’m being characteristically un-jadedly enthusiastic. Because this one might just be the real thing.
This is so good! It's a rom-com movie plot, I'd definitely watch :P!
With that said, I may not be an Italian fling (lol) but out of all the foreign people I showed around Palermo/invited to dinner with my friends and family, you were absolutely the most delightful one! Whenever you feel like getting away, my door will always be open for you Diane!!