What If It Works Out?
Or, #29. “On a plane, train, or bus don’t sit next to a woman—sit next to a man.”
It’s a Sunday in summer 2024. I’m sitting hand-in-hand on the airport bus with a boy I met at a weekend wedding, and we’re counting down the seconds to goodbye as the distance closes between Terminal 2 and Terminal 3.
We’d met at the welcome party that Friday, danced at the Saturday celebration, and spent Sunday morning together on a road trip down the Southern California coast, complete with sugary pancakes, breathtaking views, and panic-inducing traffic. Now, off to separate cities, our time together was ending. We both knew what it was: a wedding whirlwind. With an ocean between us, it was pre-determined that there was no future, yet still…there was a connection, a feeling, a spark strong enough to think we may want to keep the conversation going.
A fleeting kiss as the bus pulls up to my terminal, an awkward salute through the window as it drives to the next, and then he’s gone, leaving me with nothing but delusion and the excitement of possibility.
I knew he wasn’t looking for long distance. And, even though I knew it was crazy to think this would be anything other than a fling, I also knew I’d see him again. A wiser woman would have just left it, let the story end at LAX Terminal 3. But I’m not very wise. I’m hopeful to a fault, rom-com-addled brain always looking for a reason to believe in the unbelievable.
And so as my plane shot off into the sky and I watched the world shrink through a window, a singular question ran through my head: What if it works out?
In some ways, this story satisfies the list item “Ride the airport bus back and forth,” but that’s merely a happy coincidence for #29. “On a plane, train, or bus, don’t sit next to a woman—sit next to a man.” I didn’t plan to write about my Wedding Boyfriend when I set out to tell tales of meeting in transit. But I’ll admit, driving along the Pacific Coast Highway months ago, somewhere between Carpinteria and Oxnard, the thought crossed my mind. I was pleased with the spontaneity of the situation and wondered what, if anything, would come of it.
Still, I wasn’t thinking about that weekend when I began this essay. The only thing on my mind was Rosalie Porter, a spitfire with a transit-related love story worthy of a thousand words. I was marveling over her great romance: one that spanned distance and decades, took place over telegrams and on transatlantic ocean liners, persevered through the wrong partners and the right risks. I was thinking about how hers was a story that worked out… and I couldn’t bring myself to write it.
I didn’t know why, but I was blocked. So I stalled and requested as many motion-induced meet-cutes as I could source. It wasn’t until I talked to my friend Mia about missing her shot with Milo Ventimiglia after a run-in on the subway that a central theme crystallized.
Almost everyone has a story about connecting with someone in transit, but what unifies them all—and what was missing from my essay—was not the method of meeting. It was the nature of the event itself: random, spontaneous, surprising. The sense of adventure, excitement, the very feeling that made my heart flutter on the airport shuttle. Despite the odds, one wonders if the relationship will continue after the bus stops, the plane lands, the boat docks.
It’s less about what happens when you meet in transit and more a question of what comes next.
Enter Rosalie.
Rosalie Pedalino was 22 when she got on the Europe-bound ship that would change her life. It was 1953, and the young woman from Orange, New Jersey, had not been abroad since immigrating to the States from Italy at age six. Given the era, this is hardly surprising. Her teenage years were defined by WWII and its aftermath as countries rebuilt and recovered. A jaunt around the world wasn’t exactly plausible.
But then came the boom. The 1950s brought prosperity, hope, babies, more war, and some peace. It was an era full of contradictions: economic growth (rampant capitalism driving a wealth gap), the expansion of suburbia (redlining and the onset of Levittowns), and, of course, the iconic American family (sexism and the confining of American women that ultimately led to second-wave feminism). For many American women, the world simultaneously got much larger and far smaller than before. The traditional trajectory was simple. Find a husband by whatever means necessary (see 129 Ways), get married, and have children.
Rosalie was on that path. She’d planned a European adventure with her best friend Blanche and was all set to go when her long-time sweetheart—local banker Frank Ward—proposed marriage. She accepted and went on the trip.
The two young women set out for Europe. Blanche by sky, a newly engaged Rosalie by sea.
Rosalie met David Porter on her first day of the voyage. It was 4:00 p.m.—tea time. She was alone and eager for a companion. “I go up to the big lounge, and I look over the room, and I see a very handsome young man sitting with a newspaper.” She wistfully recollected. “And so I stroll over there, sit down, and say, ‘When you're finished with your newspaper, may I have the crossword puzzle?’ Well, he looks up at me, and he says, ‘Of course.’”
They started chatting.
David was bound for Istanbul, where he would teach at Robert College. Rosalie was engaged to Frank back in New Jersey. There was no way it would work out.
So in the beginning, they were merely adventurous friends with a motley crew of travelers. “We're on the ship nine days, and young people from all over the country are sailing to Europe,” Rosalie continued. “And it was nine days of partying. There were Smith College students. There were young business people. And all we did was have a lot of fun.”
“Orchestras played, and there was dancing every night. There were wonderful dinners, cocktail parties, tea parties. There were three swimming pools on the ship. And when we've been drinking and carrying on until two in the morning, we would go out on deck, and we would jump in the pool with all our clothes on.”
At the end of nine days, the boat docked, Rosalie met Blanche in Italy, and David headed off to Turkey. Logically, that was the end of David Porter, but even so…
She thought they might keep in touch.
What if it works out? It's 2019. Liz is on a flight from Berlin to London for a work trip. She’s seated next to a strapping young gentleman. They hit it off. She’s heard this story before—her ex’s parents met on a plane—and is hopeful as the aircraft takes off. The first hour goes great, a perfect date at 10,000 feet… and then he gets political. In a bad way. The descent turns into a debate as Liz curses herself for ever engaging with a man while locked into a seat in the sky. The next time she flies, she keeps her headphones in.
Rosalie and Blanche had been racing around Europe when a telegram arrived from David Porter. “Come to Istanbul.”
It’s easy to imagine: Rosalie holding the telegram, staring at Blanche. What if? Blanche looking at Rosalie. Why not? They made the impulse decision to cut Switzerland out of their tour and instead fly to Turkey, a place entirely foreign for a young American woman to visit. Eager for experience, they weren’t phased by the exotic location. Perhaps it was even what made the trip enticing. A week-long tour of the country ensued as David and friends hosted the women.
By now, Rosalie had decided to call off her engagement to Frank Ward. Not because of David, but because she had decided it wasn't a good match. She had seen the world and realized she wanted a bigger life than he could offer.
As for David Porter, “At that time, I saw David as a terrific guy who was fun, handsome, very bright, a friend for a fling—no serious ideas.”
It’s a tale as old as time. There was a connection, they both felt it, and knew there was no future. The best they could hope for was friendship, right?
So, they said their goodbyes. David told Rosalie, "When I get back to the U.S. in a few years, I'll want to see you—even if you're married and have half a dozen kids."
They promised to keep in touch.
What if it works out? It’s 2014. Francesca is 19 and commuting into the city from New Jersey for class at NYU. She’s on a bus at Port Authority waiting to go home when he boards. Bus Man. She notices him the second he steps on; he does the same. What if he sits next to me? She nervously frets, her heart racing as he moves down the aisle and plops in the empty seat to her right. Exactly where she wants him.
Neither puts headphones in; both are trying to figure out what to say. She spends minutes searching for gum, working up the guts to start a conversation, when he takes the plunge and asks her a question. They talk the entire ride home.
At their final destination, names—not numbers—are exchanged. But it’s 2014 and Facebook is still cool, so Francesca sends a friend request. Almost immediately, he messages her.
They date for four years. It didn’t last forever, but it lasted for long enough. “Love can happen on New Jersey transit,” Francesca commented. “I remember having this feeling of like, ‘I could be sitting next to my husband and if I don’t do anything about it then I could miss out.’ Good general life advice [is] to just do the thing. You never know.”
With David and Turkey behind her, Rosalie boards a Boeing Stratocruiser from Rome to Paris, the last leg of her six-week trip abroad. In search of a cocktail, she heads to the first-class cabin bar and strikes up a conversation with Colin Cagnacci, a charming young Australian on an extended business trip. One thing leads to another, and soon they’re dating around the world, dancing in Paris, London, and New York.
Back in New Jersey, Rosalie officially ends things with Frank and begins dating Colin—an engineer living and working in Pakistan—long-distance. Soon, he proposes, and she accepts.
They plan to marry in the States the following year, after which Rosalie will move to Pakistan. “I think that's half the reason I fell in love with him,” she said. “‘We will live in that country, and I will start writing.’ Well, it went on for about a year, and little by little, I became disenchanted.”
Once again, something in Rosalie had shifted—she knew she was searching for more than the man she met on an airplane somewhere over France. Rosalie mails Colin’s ring back and ends the engagement.
And then she takes the world into her hands. Literally. Rosalie becomes a Pan Am stewardess and continues to travel, adventuring on her own terms. She feels free.
Rosalie and David Porter still keep in touch.
What if it works out? It’s February 2023, and Malia is on a NW train bound for Penn Station. She’s going home to watch the Superbowl with her mom and running late. An early morning at work caused her to drag her feet and miss the afternoon bus. But she’s finally on her way.
The night before, Malia had received an Instagram follow request from her crush Zack, whom she’d been trading likes with on TikTok for months. She’d raced in to tell her roommate, Macy, about the development. Sure, it was an internet infatuation, but it meant something, right?
As the NW stops at 5th Avenue, Malia looks up at the closing doors. Her heart misses a beat. Walking on is no one other than Zack.
In disbelief, she looks away, nervous. No way. “Out of all of the subways, out of all the stations, out of all the subway cars, he’s on mine the next day?” The train starts moving as he cautiously raises a hand to wave at her. “Are you Malia?” He asks. “Yeah! …Are you Zack?” They beam at each other. He joins her on the bench as they dive into earnest conversation.
The train ride only lasted four stops, but it didn’t matter. They knew this was the beginning of something much bigger than a single subway ride.
Two weeks later, Malia and Zack meet for coffee. The rest is history.
Interestingly, as their relationship unfolded, they realized they’d spent years just missing each other: in neighborhoods, with mutual friends, on trains. “Our paths were parallel for so long, and then all of a sudden, one day, both of our paths just crossed, and that’s the way that we are now. We’re together.” She remarked fondly. “The right person could always be the right person, but if you don’t meet them at the right time, it might not work out the way it was meant to.”
It’s September 1956. David Porter is home from teaching in Turkey, now in the army, and is on leave. He gives Rosalie a call. It doesn’t take long for each to realize how deeply they care for one another. An engagement is planned. After years of passing ships, they have finally docked: they’re both single and in the right place at the right time.
But then… it falls apart as quickly as it came together. “On talking with my local priest about a marriage ceremony, we discover serious religious differences—so difficult to resolve that we break up.” David returns to his army base, and Rosalie goes back to Pan Am.
The engagement is off.
What if it doesn’t work out? I’m an ocean away from New York, at dinner with the man I met at a wedding several moons before. I’m nervous. What felt like months of talking had led to this meal. What would happen now? I babbled away, sharing flight details and playing with the remnants of my Sunday roast. Where do we go after this? Had it all been in my head, was I delusional, or was there possibly—
“I’m so glad we were on the same page,” he reached across the table and looked at me earnestly. “About what this was.” I cleared my throat and finished the last of my wine.
We didn’t keep in touch.
A single Rosalie is en route to Washington, D.C., to visit Blanche and her husband. It’s 1957. Rosalie is an older and wiser woman than the 22-year-old who got on a boat to Europe in 1953. She’s well-traveled and sure of herself.
She knows what she wants.
Unwilling to let a good thing go, Rosalie reaches out to David, who is now in D.C. for the summer and preparing to return to Istanbul to teach.
They meet again; this time, it’s end game. Now or never. David proposes. Rosalie accepts. Ten days later, the newlyweds leave for Istanbul.
They adventure together for 56 years, until David’s death in 2013.
Malia and Zack are still together, and they still ride the NW. “Any time we’re taking the train, we always give each other a kiss and tell each other we love each other when we get to 5th Ave. When we aren’t together, we’ll text each other every once in a while and just say, “5th Ave ❤️.”
Rosalie and David had three sons. Eventually, they moved back from Istanbul to the States. Rosalie went on to get her degree, then her doctorate. She traveled the world consulting and was able to achieve all she had dreamed of: finding a life partner, becoming a parent, and pursuing a career as a writer and activist. Rosalie has lived a life full of stories, but I’ll let her tell the rest. Her book American Immigrant: My Life in Three Languages is linked.
Francesca graduated from NYU, got off of Facebook, onto Hinge, and found someone new. She’s still in New Jersey, but moving to San Francisco next year.
Liz is talking to people on planes again, but she keeps her headphones close by in case the conversation takes a turn for the uncomfortable.
And as for me, I am still waiting, wishing, wondering when—not if—it’ll work out. I’m trying to sit next to more handsome strangers while in transit and hoping if a conversation inspires, it’ll be more Before Sunrise and less Strangers on a Train.
The tales I’ve heard are inspiring, regardless of their outcome. I’m endlessly grateful to all who shared their little love stories, but especially Rosalie, who reminded me of the merit and power in pursuing a big, bold life. To trust your gut, not settle for anything less than magic, and know that things will be okay.
Time changes how we keep in touch; a telegram in 1953 might be a TikTok DM in 2025, but the sentiment is the same. All it takes is a chance meeting to spark something special. It’s the right place, the right time, and the right person. The rest will figure itself out.
When Rosalie first saw David in 1953, she thought, “Let me go see. It was an instant of impulse, never thinking that anything would come of it, of course.”
What if it works out? It doesn’t until one day, it does.
I love this view, I think sometimes you just have to go with your gut and see where it takes you. It’s all part of life and growing through the process. 💕
Oh wow this was so beautifully written. 💛