I Had My First Fling at 58

What started as a trip to Italy to see art ended with a whole lot more than that.

“In una città piena d’arte, sei ancora l’opera più bella,” said the tall, slim Italian man. He had beelined toward me outside a skinny bar anchoring a crowded piazza, as a local band played Americana music.

“I don’t speak Italian,” I declared bluntly. I can get standoffish when I’m attracted to someone so good-looking they feel out of my league.

Undaunted, he gestured to my eyes, exclaiming, “Bellissima,” and clinked his glass into mine.

My 58-year-old face blushed.

When the Trump Administration and Department of Government Efficiency (DOGE) dismantled the US Agency for International Development (USAID) in February 2025, the career I had spent 20 years building went up in flames. No longer a strategic communications advisor for a democracy and governance initiative, I drank a lot and felt dead inside. Lured by a $650 round trip airfare, I booked a last-minute trip to Palermo two weeks before Christmas. I hoped immersing myself in awe-inducing art would make my senses come alive. I had seven days to find out.

Pointing to himself, the Italian said, “Salvo,” before he pointed at me.

“Alex.”

“You put your Instagram,” Salvo said, holding out his phone.

I typed in my handle because Salvo had full lips, dark eyes, and chin-length wavy dark hair—so handsomely my type. When the music picked up, we boogied like Serpotta’s putti in the December dusk. But Salvo’s hand kept finding my bottom like some Whack-A-Mole version of Twister, with my butt always on the spinner board. I’d retreat out of his reach, hoping he’d get the message. When he didn’t, I ditched him.

Walking back to my Airbnb, I was haunted by a thought: How much longer would sexy men find me desirable? Back home in Tulsa, men’s beards range from Colonel Sanders to jihadi to ZZ top, so not my vibe. I was in Italy! Why not have a fling?

I’d never had a one-night stand, though, and I wasn’t sure if age 58 was the time to start. I still suffered from the hangover caused by drinking too much patriarchal cocktail: two parts good-girls-from-nice-families to one part Catholic guilt, with a cherry on top.

The next morning, Salvo slid into my DMs, inviting me for a drink. I agreed to meet him at a different piazza.

He pulled up on a Vespa. “It’s OK?” he asked, gesturing to the scooter.

Any true crime lover knows nothing good ever comes from letting a total stranger take you to an unknown secondary location, but I was more concerned with how I’d mount the scooter in my column fit, ankle-length leather skirt and not flash my panties. Ignoring the murderino voice screaming Nooooooooooo! inside my head, I hitched my skirt high enough to hop on.

There’s something quixotically cinematic about hanging onto a sexy man’s waist as he weaves you through an architecturally undulating city. For the first time since being DOGEd, I felt like I had taken center stage in my own story. Salvo stopped at a wine bar near the port, where we lolled at an outdoor table. He spoke much more English than he had the night we met, which made me wonder if he’d had a Babbel cram session since I’d seen him.

He told me he was 39, but mercifully did not ask my age, and had one daughter. The date was going great until he tried to pack on some PDA, which I find disrespectful but his tactile Italian tongue did not. Although I’d duck and cover, he didn’t take the hint, so when he asked me to wait for him while he brought his daughter some dinner, I declined. He messaged me 90 minutes later, suggesting we resume our date, but much to my libido’s chagrin, I didn’t answer. I wasn’t sure I wanted to sleep with him, yet defending my boundaries felt like a herculean effort.

The next morning, I was standing inside a church, drinking in color-drenched ceiling frescoes when WhatsApp pinged with a vague apology and a drinks invitation. I typed, “Are you apologizing for interrupting our date to bring your daughter pizza or for disrespecting my request not to be kissed and pawed in public? One is OK. The other is not,” and hoped he had activated his WhatsApp translation feature.

“Of course, I apologize for everything…let me know if you want to see us with great pleasure…sorry again.”

“I will let you know later,” I answered before heading to the Capuchin Catacombs.

Nothing like a crypt of 2,000 clothed skeletons to remind a person that life above ground is ephemeral. I made my way to the hall housing deceased virgins, pristine and preserved in their embroidered clothing, with ornamental caps or metal crowns on their heads. Near the exit stood a 526-year-old mummified monk, who’d also probably never gotten laid.

Should I forge a holiday romance? I asked him in my head.

Escaping into the daylight, I messaged Salvo, setting up a time and place to meet. Then I hustled to Intimissimi, Italy’s answer to Victoria’s Secret. The Giola Super Push-Up made my sagging C-cups look vulgar. The plain Francesca Ultimate T-shirt looked great under clothing but not by itself, which defeated my purpose. Was I a Denise Lace Balconette or a Sofia Pretty Flowers? I got them both with matching undies.

We met at a bar near Salvo’s apartment. With our knees touching under the table, he took my hand in his and delivered a heart-felt apology with an assist from Google translator. I watched him realize in real time why I had ditched him the night we met. He covered his face with his free hand before apologizing earnestly and repeatedly, pulling me close. For the first time, I appreciated him for more than what he looked like.

If this were a rom-com, my lingerie would have activated a Wonder Twins superpower of nonchalance. I would have gone home with Salvo, and we’d have had multiple rounds of orgasmically long-lasting sex until the sun rose, bathing my face in youth-infusing golden light. I would have left his apartment renewed and ready to take on the world in a single bound.

I didn’t.

Four times engaged but never married, childless, and fiercely independent, I had recently started dating based on aesthetics alone. I figured, I have great friends and freedom. (My last long-term partner Jekyll-and-Hyded into a jealous, controlling manipulator.) Maybe I didn’t want a partner after all. But sitting across from Salvo at a small bistro table, our upper thighs interlocking like puzzle pieces, my hand in his, I realized I wanted something more than good looks. So, despite feeling tipsy and ambitious, I asked him to Vespa me home.

Back in my Airbnb, my insecurity, yearning, and regret slugged it out, with no real winner. Twenty years ago, a few months before my first deployment abroad, I started renting a room from an Italian punk rocker in an ungentrified Brooklyn neighborhood. He worked days while I worked nights, but when I’d get home from a shift, he’d be up, and we’d have these epic, hours-long conversations around our kitchen table, like old-timey Italians.

Our mutual attraction was obvious to friends, neighborhood bartenders, and to each other, but he didn’t act on it. The morning he drove me to the airport, I asked him why. Sitting in his parked car in the gray January cold, he admitted he hadn’t made a move because I was leaving, and he didn’t want to get hurt. I hadn’t cared about our built-in expiration date because, back then, I lived by the motto: dare to leap. If he had been willing to jump with me (I wasn’t going to push him), I would have enjoyed the soar before the fall. Sitting alone that night in Palermo, I realized I had lost my nerve to jump.

Salvo messaged the next morning, my last day in Palermo, inviting me to meet, and I accepted. We had just begun la passeggiata, the traditional evening stroll, when his phone rang. A water pipe had burst at the family’s business, and he needed to take care of it.

Several hours later, Salvo was ready to resume our date. He wanted to spend the rest of the night together until I had to leave for the airport in the morning. I was salty from waiting and tempted to call off the sexcapade, but I knew I’d regret missing this opportunity. When I am very old and reduced mobility has shrunk my world to the confines of a mattress, I want my shouldn’t haves to outnumber my should haves by a lot.

Salvo picked me up on his Vespa and whisked me back to his nondescript yet completely functional man pad. After a 90-second tour, he poured two glasses of wine and set them on the coffee table in front of his sofa. We sat and sipped. Sip. Sip.

We pounced on each other.

Trading the sofa for his bed, nobody was disappointed. Both times. 

I went into his bathroom and was negotiating the bidet when I heard him talking. I opened the bathroom door, which was catty-corner from his front door, and found Salvo standing in the open doorway, fully clothed.

“Whoa!” I was stark naked. Anyone coming up the stairs or passing by his front door would have seen me.

Salvo responded in unhelpful Italian as I ran into his bedroom to find my clothes. Once dressed, I re-entered the living room, wanting my wine, but our glasses had been whisked away.

“My uncle…fight with his wife…sleep here,” Salvo said, handing me my coat. “I take you back.”

So much for staying together until morning. I refused to hold onto his waist or let my torso touch his as we sped through the rain-slicked streets on his Vespa. When he dropped me off and leaned in for a goodbye kiss, I pulled away. My night of Italian passion, including travel time in both directions, had lasted less than 52 minutes.

Four hours of sleep, three flights, two layovers, and one rideshare later, I was back in my Tulsa apartment, staring at my Charlie Brown Christmas tree. My WhatsApp filled with messages: apologies, a declaration that family members would no longer disturb him at home, a hope for me to return to Palermo, a request for photos of my city, and lots of kissing face emojis.

Ten months later, heart emojis and short messages fly back and forth across Instagram and WhatsApp. Having a handsome Italian to think about as I negotiate big life changes—moving to a larger city with a better job market, job searching after a career pivot, grieving a beloved aunt, and worrying about my one remaining aging parent—is welcome escapism. Frankly, I am surprised we’re in contact. We don’t speak much of a common language, yet he makes me feel seen. Now, after more invitations to return and two specific invitations to stay with him when I do, I have a ticket to Palermo in November. I may still be re-learning how to jump and take flight, but I know enough to book my own Airbnb.

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