The Era of Nonchalant Dating | Travel Dating Diary - December 2025 (Part 11)
The 2025 finale of Romance by Rail took me from the Shakespearian streets of Verona to the Bay Area, tech bro capital of the world, yearning for profound mutual enthusiasm but instead discovering something I was not anticipating...a whole Era of Nonchalant Dating.
In December, I dated the following guys: 1 Estonian, 1 Italian, 1 Serbian, and 1 Indian.
There's a ghost who gets caught red-handed mid-ghost, a smolder-then-vanish situation, and a perfectly normal nice guy who just wasn't bringing the poetry.
Two years into this idealistic project, I was truly ready to call it quits. Nonchalance dating finally got the best of me.
Time for a break and some soul searching as to whether I still want what I set out to find.
Travel Route
I traveled from/to:
Padua, Italy —> Verona, Italy - train
Verona—> Trento - train
Trento —> Bolzano (with day trips to the Dolomites and Merano) - train + rental car
Milan —> San Francisco, California - flight
Oakland —> San Luis Obispo - train
How long I was in each place:
Northern Italy - 2 weeks
California Bay Area - 1 week
San Luis Obispo, California (my hometown) - Dec 17th, 2025—March 18, 2026
Dates:
For first-time readers—all the guys in my blog are called “John #” in the order of dating or meeting, but the “John” is in their home country’s language.
Verona & Trento - 2
Jaan 47
Giovanni 48
California - 1
Yuhanna यूहन्ना 49
“I Don’t Really Care”: The Era of Nonchalant Dating | December 2025
Remember back in 2018 when Melania Trump infamously wore that army green canvas jacket with these words printed on the back, in white lettering: “I DON’T REALLY CARE, DO U?” She was photographed while boarding a plane to visit New Hope Children's Shelter in McAllen, Texas, where migrant children separated from their parents were being housed. Was she mocking migrant children? Was she telling us that her visit was performative? We may never understand why she chose to wear the jacket that day, but it quite literally spelled out something disturbing: a lack of care for others.
For those of us disturbed by her choice in messaging that day, our unease extended beyond the moment. Did she represent a greater public sentiment in not caring? How could America elect a man who bragged about assaulting women, who mocked disabled people, and who hosted a reality show centered around brazenly firing employees with contempt? Had we stopped caring about each other?
Maybe sometime between creating a Facebook profile in the aughts and the release of TikTok and Instagram’s short-form video content during the global pandemic, we got pulled into virtual reality and out of real-life experiences. Maybe we started to hate people online and forgot to love our physical neighbors.
As we, on a societal level, became increasingly dependent on new, personal tech gadgets, more internally focused, and less social, this seemed to be reflected in attitudes toward dating. Especially in the years since the pandemic subsided, I’ve noticed more and more women creating the aforementioned short-form video content on something dubbed “nonchalant dating”.
nonchalant
/ˌnänSHəˈlänt/
Nonchalant (adjective) describes a person or their manner as feeling or appearing casually calm, relaxed, and unconcerned. It often implies that someone is—or is pretending to be—indifferent, not easily bothered, or not displaying any anxiety, interest, or enthusiasm. [1, 2, 3]
Nonchalant dating, which all the single ladies have been griping about, in which men seem not to care or put in any effort, has seemingly become the norm. Women text first. Women pitch and plan dates. Women follow up over text. Women are ghosted with zero communication.
Is this simply a part of this cultural tech wave in which viewing people across screens has made us devalue them? Or is male nonchalance also a reaction to big strides in women’s rights in recent years, especially in a post-MeToo world in which we’ve called out abusive and violent male behavior in a big way?
We can point to an overarching trend of nonchalance in the USA in ways big and small. In 2018, when we all saw the horrors of child separation at the border, many looked the other way, continuing the fervent support of our belligerent and evil President.
Or were we anesthetized during the pandemic when the weight of knowing that we could accidentally cause someone’s death just by breathing was too much to bear? When we lost 1,235,885 American lives to the COVID pandemic, was this simply a loss too great to comprehend and metabolize?
Every time we normalized some new horror, missing outrage and accountability, we went numb. And while we turned down the dial of our hearts to feeling bad feelings such as grief, anguish, and rage, we eliminated our capacity to feel good feelings in the process: excitement, wonder, and desire.
At some point, social media put us in a house of mirrors. We started to see others’ FaceTuned digital representations, and we thought we could try to emulate the trickery in real life. Celebrities such as Kyle Jenner said, “No, no, no, I’ve never had any work done. No lip filler!” while asking women to buy a “lip kit.” Later, when she admitted that it wasn’t merely her $20 lip kit, it was several milliliters of hyaluronic acid, injected with a needle at 1000 bucks a pop, she was already a billionaire. Not to be outdone in internet fakery, men got influencers like Andrew Huberman, who started selling supplements while never admitting to his anabolic steroid addiction (but one look at his egregiously chonky neck and a perusal of the exposé about his aggressive relational behavior would tell us otherwise). With so much fakery and objectification in our everyday lives, it was only a matter of time before dating and long-term committed relationships took a hit. Standards became impossible.
And with the swipe apps like Tinder and Bumble, when the options have seemed limitless, couldn’t we always hold out for someone seemingly perfect? Why settle for imperfection when the most optimized partner is surely around the corner?
As nonchalant dating started to seep into the realm of what’s normal, many of us forgot to hope for a love that felt deep, true and mutual.
As my second year of travel dating—of this Romance by Rail project—started to come to a close, I realized that I had forgotten that a really good connection should feel mutual—that there’s an excitement about the person, and you can feel excitement from them too. My standards had been lowered to accept less effort, less excitement, and less hope for something celestial.
A counterterm started to appear: “chalant dating”. “Chalant” is not a word, btw. It’s just a funny way of saying the opposite of “nonchalant”. “Can ‘Chalant’ Dating Help More People Find Love? Ask Taylor and Travis” was a piece in the New York Times a couple of weeks ago by journalist Chloe Shakin. Tay stans are apparently seeing the mutual, if not outright dorky, enthusiasm that Taylor Swift and Travis Kelce have for each other and yearn for that kind of unreserved passion and commitment.
“The Swift-Kelce relationship has some single people pining for partners who will show up for them with unbridled enthusiasm — a man who will broadcast his interest in you on an episode of his podcast before you’ve even met, a woman who will cheer you on from the sidelines and rush onto the field after your big win.
Instead of remaining mysterious and aloof, some singles say they are now seeking partners who are the opposite — or “chalant.”
Chalant — pronounced like its foil, nonchalant — is a made-up word echoing around the internet. In dating, it refers to a state of unabashed excitement and affection, rather than playing hard to get.
“It’s about putting in effort and showing vulnerability, even at the risk of rejection,” said Logan Ury, a behavioral scientist and dating coach who is the director of relationship science for the dating app Hinge.
Chalant dating is a positive shift, Ms. Ury said, “towards people feeling comfortable wearing their passion on their sleeve a bit more and just going after something — and not trying to win that battle of who can care less.”
In chalant dating, or secure dating, we’re not worried about every small potential misstep (such as last summer when Can 18 read my blog about him and used it as an excuse to break things off for the second time). There’s that phrase you sometimes here in dating advice circles: “You can’t say the wrong thing to the right person.” If there’s mutual excitement and both people are putting their most chalant foot forward, they can forgive each other for slight transgressions such as saying something awkward, taking too long to text, or double- or triple-texting. There aren’t really transgressions when you both like each other the same amount and you’re willing to be cringe about it. With a great match, you keep finding ways to connect, and you find ways to extend compassion instead of everything being a red flag.
In the last few months of 2025, I found myself forgetting what a great, passionate, and mutual match once felt like. I entered this dating project wide-eyed and bushy-tailed, excited for the possibilities and all of the interesting people I was going to meet and get to know, and after too many nonchalant hit-and-runs, ghostly ghouls, energy vampires, and emotional zombies, I realized that I would need to either end my project for good or at least take a really solid morale-restoring break. Nonchalant dating burned me out! I needed to find my inner chalance.
This makes me think of Owen Wilson’s character in the 2006 film You, Me, and Dupree, in which he talks about a person’s “inner-ness,” the sparkly thing that makes someone themselves. I needed to find my chalance-ness, my Alison-ness again before I could keep going.
The Two Gentlemen of Verona
The Two Gentlemen of Verona, written some time between 1589 and 1594, is considered one of Shakespeare’s earliest works. It is set in Verona and Milan. The play features two men, and the “gentle” part means that there was some family wealth just a notch down from the “noble” class. These two well-to-do dudes go about trying to find brides, with shifting loyalties to the various female characters, in classic Shakespeare comedy fashion. Characters seem to forget their undying professed love as soon as their crush leaves the room or as soon as their friend’s crush comes in. Hijinx ensue, including one episode of secret spy crossdressing, ending in a romp in the forest in which everyone comes to their senses as to where their loyalties lie, although not after Gentleman 1 says to Gentleman 2, “Okay, fine, you can have my crush if you really want her, even though you earlier proclaimed your love to the other one.” This act of generosity inspires him to find his true chalant-ness, and he chooses his original love after all.
In December, I encountered two men of Verona, who, like me, are perhaps a notch below “Gentle”—two Workingmen of Verona. In a tale as old as at least 400 years, loyalties, manners, and clear communication were somewhat misplaced.
However, the unbridledly enthusiastic and chalant, obsessive, romantic, pining, fiending, and most assuredly cringe kind of love, full of dramatic words and maybe a sword fight or two, seemed notably absent.
Verona might seem more familiar to you as the setting of Shakespeare’s most famous work, Romeo and Juliet.
"Two households, both alike in dignity / In fair Verona, where we lay our scene"
In this play, we see hasty, young love and the poorest of communication, but why is it considered peak romance?
Because the young lovers go all in.
Every character is full of passion. No one is playing it cool by pretending they’re not that into the other. Love is celebrated as one of our highest quests, one worthy of risking violence at the hands of feuding families, and ultimately, the end of their lives. The love is immediate and intense.
Most of us saw one or both of the movie renditions of this classic, either the 1968 version or the 1996 one starring Leonardo DiCaprio and Claire Danes, or the 1961 West Side Story musical film. Maybe these tellings of chalant love got etched into each of our brains with each viewing—that we’d meet someone willing to betray deep-seated family feuds over. We’d meet someone who felt like destiny.
In 2026, Romeo and Juliet would be double- and triple-texting furiously.
My experience with the two gentlemen of Verona, whom I met while in Italy, carried the themes of crossed communication lines without the star-crossed love.
Jaan 47 | Estonian | Mid 30s | Bumble App
Enter nonchalant gentleman of Verona #1.
Our text conversation felt pretty fun. Quite a bit of easy banter and mutual curiosity. He explained that he had moved to Verona from Estonia and had been living there for a few years. From his photos, he had boyish good looks with a cheerful, round face and a mop of curly light brown hair. Working in the tech industry, he donned the trade uniform: chino pants and zip hoodie sweatershirts. He often donned a large ear-to-ear grin.
We matched on Bumble while I was in Venice, and I told him that I had plans to apply for the Remote Worker Visa in Italy and was spending a few weeks looking at cities where I might want to live, with Trento being at the top of my list. My trip companion, EL, and I realized that we had to transfer trains in Verona on our way from Padua to Trento, so we’d spend the day there.
I asked if he wanted to meet for coffee or lunch and explained that I was with my friend. Of course, I realized that these could be less than ideal circumstances for meeting up, but I’m also of the belief that it’s important to see each other quickly after matching and before wasting a lot of time texting, because you can only gauge mutual attraction over a video or in-person meeting. So, I thought it could be something casual and brief to see whether there was enough mutual interest and attraction to start dating.
He said that yes, meeting for coffee or lunch the next day, a Monday, sounded great. Great!
The next morning, I texted him my train arrival time. “We’re getting in at 11:37,” I let him know precisely. In the way that texting is an exchange back and forth, and that Verona was his home city, not mine, it was now his job to text back, suggesting a time and place.
But no time and place text arrived. Instead, he sent a guide to Verona. “What is this?” I showed EL, confused. Is this his way of saying, “Have fun out there!”??
“I just don’t get it,” I lamented to EL. “What is this vague communication?” I felt more than a little frustrated and confused.
No big deal. We were happy to tour the city sans coffee or lunch date with a stranger. We stopped at a delightful bakery with beautiful cakes in the window and tried nearly one of everything—at least of the tiny pastry offerings. We headed into town and saw the famous Verona Arena, which was built in…if you don’t audibly gasp, then maybe you don’t have a pulse…wait for it…30 AD! It’s pictured above, and apparently, a major earthquake in 1117 destroyed much of the outer ring, but the inner structure remains well-preserved.
We got lunch at a hip, modern cafe with fresh things on the menu, ordering salads and feeling a bit like we were back in California. We found Juliet’s balcony, which became a tourist attraction in the 1930s to enhance the romantic appeal of the city. Of course, there was no real Juliet in Verona, but one could certainly imagine the angst and longing of teenagers past and hope that they may have called out to each other over many such balconies for hundreds of years.
There was a life-size statue of Juliet, rubbed golden by people’s many hands, clamoring for some of her magic.
“My bounty is as boundless as the sea,
My love as deep; the more I give to thee,
The more I have, for both are infinite.”
― William Shakespeare, Romeo and Juliet
We walked alongside a castle and the gorgeous river flowing through the middle of town, taking many photos. We oohed and ahhed as we turned every corner at the beauty of this city. After several hours, we felt done and started to head back to the train station, following the route designated by Google Maps.
Our winter beanie-clad heads were down, and our hands were deep in our winter coat pockets. We headed there briskly, hopeful to arrive before it got completely dark. A 1-hour train ride was ahead of us and a check-in to our Airbnb rental at our next destination, the mountain town of Trento.
I glanced up and saw someone familiar walking on the sidewalk directly ahead of us…which was strange because neither of us had ever been to Verona before in our lives. Suddenly, I recognized him—it was Jaan 47 from Bumble! The ghost himself!
“Hi Jaan,” I said as he approached us on the sidewalk. I waved until he stopped. I watched the realization hit him and turn into dread. I introduced him to my friend. I introduced him to me, shaking his hand. I told him we were heading to the train station. He told us he was heading to buy some groceries.
We stood there on the sidewalk for a beat too long, my head cocked to one side and my gaze intently staring at him, demanding a reason. But no reason was forthcoming. He did not say, “Sorry, I just dropped off when I said we would meet.”
So we just stood there until I said, “Well, we have to catch our train.” I let him go without any confrontation.
EL and I walked in silence for the rest of the block until we were out of earshot. Then, explosively, “What the fuck?!!?”
“He looked so sheepish!” EL said. “He knew he got caught.”
“He did look embarrassed, didn’t he?” “Completely!”
It just didn’t make any sense! I didn’t even know him yet. He could easily say, “No, I don’t want to meet.” He could even say, “No, I hate your face,” and I wouldn’t care! He’s a stranger. It didn’t matter. It wouldn’t hurt my feelings. Onto the next match! Why ghost? Why just stop responding?
And then I did something that surprised even me. I started crying.
I was so deeply tired of all the mixed signals, missed connections, and immature guessing games…exhausted in my bones. “Why not just say, ‘No, I don’t want to meet’?? Why say yes if you mean ‘no’?? I don’t get it. What is the deal with these men? Why is there always something a little off?” I sobbed to EL. “I know it’s like this.” She threw her hands up, sharing my exasperation. “That’s why I had to take a break from dating.”
The Romance by Rail project felt like an abysmal failure. Between personality disorders, attachment disorders, and addiction to adult graphic content, I was getting nowhere. How many more first dates did I have in me? How much ability to shrug off all of these micro-slights did I have left after 2 years of travel dating?
It took 2 years, but the project had lost its sparkle. This type of attitude would never attract my soul mate. I felt so far from the Candide-like figure who naively set out on his world travels thinking “everything is for the best”. I had indeed discovered that the world was horrendous much of the time and that I might need to retreat and tend to some small plot of garden somewhere, minding my business. I’d been too ambitious. Too dreamy. Too delusional. The version of me who had felt inspired to start the project after 5 dates and a whirlwind romance in the Fall of 2023 was inspired, excited, and curious. Now I was feeling downtrodden, defeated, and full of dread at the prospect of having to continue dating.
“It is my lady. O, it is my love!
O, that she knew she were!
She speaks, yet she says nothing. What of that?
Her eye discourses; I will answer it.
I am too bold. ’Tis not to me she speaks.
Two of the fairest stars in all the heaven,
Having some business, do entreat her eyes
To twinkle in their spheres till they return.
What if her eyes were there, they in her head?
The brightness of her cheek would shame those
stars”
― William Shakespeare, Romeo and Juliet
The all-encompassing, wholly captivating, and maddening type of love that clouds all reason, a love of mutual obsession…I hadn’t found it yet. And I was starting to believe it was just the stuff of fantastic plays and musicals.
These types of TikTok videos and Instagram reels have become common. A man asks a woman on a date and then doesn’t text her to set up a time and place. Part of the nonchalant experience of this era.
Trento, Italy
Giovanni 48 | Italian | Early 30s| Bumble App
Nonchalant Gentleman 2 of Verona made a valiant chalant effort to start.
EL and I made it to our little mountain town of Trento, and I continued to swipe on Bumble. I matched with Giovanni 48 who lived in Verona. His profile said he did CrossFit “ogni tanto” or “every now and again”. He had a handsome face and a bald head which seemed to suit him well, actually. In one photo, he smiled broadly with no teeth showing but a dimple on one side. He was decently tall with brown eyes and a deep, pensive gaze.
We texted for a few days, and it was interesting enough that we agreed that we should meet. I invited him to come all the way up to Bolzano, our next destination, for a festive Christmas market weekend trip. At first, he thought this sounded nice, then let me know that it was a bit too far—a two-hour drive from Verona.
That would be quite a trip for a first date! What’s the most you’ve ever traveled for a first date? In month 1 of Romance by Rail, Juan 2 traveled by plane from Madrid to Zurich to meet! But we had FaceTimed three times beforehand, so it wasn’t a blind first date.
We talked by phone and agreed to meet in Trento on a weeknight evening, after my friend EL departed. I had a couple of extra days before heading back to the US to look at apartments for sale and see if I wanted to relocate to Trento, applying for the Digital Nomad Visa.
“I wonder what his teeth look like,” I said to EL. This made her wince a little. She hadn’t had braces and had a few teeth out of alignment, which was a small insecurity. I hadn’t meant to be insensitive. I just always wondered what someone’s teeth looked like if they didn’t show them in the photos.
“I like crooked teeth,” I told her, which was completely the truth. “Teeth that are too perfect give uncanny valley. And we’re so flooded these days with influencer and celebrity teeth, which have been veneered to eerie perfection. I like real—character.” I myself have a less-than-perfect smile, with gums that take up a lot of space and somewhat small, chicklet-like teeth. I used to be insecure about my gummy grin, covering my mouth with my hand when I laughed, but as I’ve gotten older, I have embraced my cute teeth and have dropped the smile-covering gesture.
Sure, certain teeth are legitimately not hot, and I’m specifically talking about teeth that are stained gray or dark brown and seem clearly neglected. But this handsome CrossFitter didn’t seem like that type of guy.
“But I’ll bet he’s self-conscious about his teeth,” I guessed. I pictured a cute little gap between his top two front teeth.
The day after EL and I spent in the snowy Dolomite mountains, as captured in these photos, I could feel that I was starting to come down with something—a cold, maybe. Our winter gear wasn’t quite hefty enough. We were doubling up on thin winter puffy jackets, but had needed something more substantial. We had thought we could get away with it, but it seemed to be catching up with me.
I wanted to shake it off quickly, so I kept my date with Giovanni 49. When the day of our date came around though, it turned out I had been unreasonably optimistic. I walked into town to meet him with a runny nose and some chills setting in. I certainly didn’t want to give him what I had, and I began to feel guilty that I hadn’t canceled! And on the other hand, I was flying back to the US in 2 days, and if there was the potential for a real connection here, I didn’t want to lose it.
Our text conversation so far had been better than most. He responded thoughtfully to the prompt on my profile: “What’s a book you read that changed your life, and how did it change your life?” He said it was Pillars of the Earth by Ken Follett because “it’s one of those books that shows you how passion and determination can build something great, and it taught me to do some things well you need patience.” I loved this response and told him that I had been working on patience and long-term thinking/planning myself lately.
He responded, “I’m curious what made you decide to start working on those? There’s usually a good story behind that kind of growth [wink emoji].”
I learned about 20 dates ago that it’s best to avoid trauma dumping. Yes, of course I had a good story! But was now the right moment, 4 lines of text in, to share how my life’s many failings?? [It was not].
I used my usual flirty line “Oh wow that really feels like more of a 3rd date question [upsidedown smiley emoji].” You can steal this line if you want. “That’s more of a 3rd date question” not only skirts certain topics but it implies a first date going well enough to lead to both a second and third date, which is enough to make someone blush. It’s a great dating app line.
He said he’d stick to lighter topics for now and pivoted well. There was great “serve and return,” which means we were both asking questions and following up on each piece of the questions, not leaving anything out. We were well attuned. It was definitely a good idea to meet.
When we met in the main plaza by the grand fountain, a stately piece featuring an 18th-century bronze statue of Neptune holding a trident, I gasped a little on the inside. This man was seriously hot. His giant biceps and broad muscled shoulders completely filled out his black leather bomber-style jacket with knit sleeves. His posture was sturdy. He wore athleisure sweatpants and tennis shoes as though he’d headed over after sports practice.
“He’s like the hot kind of hot,” I texted EL during the date, “A little intimidating.” It was clear that he did not CrossFit “every now and again”. CrossFit was this man’s whole life!
EL didn’t miss an opportunity to tell me “How the tables have turned!” I had often complained that every single man I dated had told me “I’m intimidated by you” and how I longed to find someone who saw me as just right—an equal.
We said our initial greetings, and wouldn’t you know it, I had guessed exactly right: a cute gap between his two front teeth. He had nothing to be self-conscious about. They suited him!
It was a holiday that day, and Trento was absolutely swarmed with Italian visitors looking to get some Christmas shopping in at the markets and enjoy their day off from work. Giovanni 48 was flustered by the crowds, which he shared with me. He had picked out in advance a few places we could get lunch, which I found very sweet, but as we walked to each place, we discovered lines out the door at each one. He started to get discouraged. He had planned well, and now things weren’t going as he’d intended. We decided to grab food from the crowded Christmas market stalls and then found a place to stand and eat while getting to know each other.
After standing for so long, I suggested that we walk to a nearby castle and sit in the garden. I was feeling tired from my cold.
We sat down on a bench in the castle garden, an optimal spot in my opinion—romantic in an old fantasy kind of way. But he didn’t seem comfortable and conversation felt tough. I’m relentlessly grateful that my dates speak English, since I’m not fluent in any other language except my own. I studied Spanish and Dutch for many years and a mere semester of French, but I can’t keep anything fluid going in these languages. I can ask where the toilet is and order a coffee, but that’s about it.
Giovanni 48’s English was proficient but not quite fluent. I often had to ask him to repeat himself, and sometimes even after repeating, I had to give up understanding more precisely what he was saying.
While walking to get food, he was trying to explain the reason for his recent breakup with his live-in girlfriend of many years. “We-eh, stopped-eh getting along-eh. Arguing all of the time-eh, it seemed-eh. And I don’t like this…this…this type of relating. I don’t like-eh…” He tried to find the words.
“Conflict?” I offered.
“Conflict, yes! I don’t like-eh conflict.”
I nodded with a half smile, reflecting on how I’ve come to know that conflict is the backbone of a healthy, connected relationship.
When people say they don’t like conflict, often what they’re really saying is that they don’t like accountability. In a healthy relationship, we have to say maybe once a week, maybe three times a day, “Yes, I did that, and I’m sorry it impacted you that way.” When partners aren’t bringing up conflicts and offering accountability, emotional distance grows. Verbal fights explode out of the emptiness.
Without conflict, we never get the chance to learn about the person’s inner world. We never learn what they value, what they feel, or what their childhood wounds are. We never learn the ways in which we experience life differently. We never learn to stretch ourselves to care about someone’s unique needs, which are different from our own.
Conflict provides the opportunity to care about people and to invite others to care about us. It’s not only beautiful, but it’s the core component of intimacy.
“But maybe something was lost in translation,” I thought.
The date felt a lot like a job interview. He wanted to know if I was dating other men. He wanted to know my 5-year plan. We even talked about our respective current incomes.
It was strange because when he first messaged me, he seemed to have some regard for the soul of things. But that wasn’t coming across in person.
Reasons I came up with:
It takes time to open up to someone, and people get nervous on first dates
His English wasn’t great, and my Italian is non-existent
I was feeling under the weather
But the honest and simple truth of things is that we weren’t a great match. We were an okay match, maybe even a good match with a few more dates, but not a great match. Not enough in common.
And it would have been nice to realize that at the time. But I was feeling defeated in my final days in Europe, as I prepared to return to California for the Christmas holiday—I’d set out on another year of travel-dating and failed again. Even though my stated goals were around feeling curious and adventurous, at the end of the day, I still wanted to meet a soul mate.
Giovanni 48 told me he had to leave a little earlier than intended because it was his cousin’s 9th birthday and showing up for his family is important to him. I couldn’t decide if this sounded like a made-up excuse or not, but either way, if he had been enjoying the date, he might have decided to skip it. That’s how motivation works.
I felt rejected, so I mentally retreated and started staying quiet.
After eating our meal, we stopped by an espresso bar for an espresso, which we drank at the counter, then we went for an Aperol Spritz at a cafe in the main square. It felt like a master class on Italian dating culture. Spritz on the plaza? Check. After meal espresso? Check.
We watched the hands on the big clock tower turn near 4:30 PM, and so we left the cafe, walking towards his parking spot and my rented hotel room. When we got to the corner where we would part ways, he said, “Oh, no, I’ll walk you home.”
This felt like an incredibly mixed signal. If he wasn’t enjoying the date, he should just head towards his car and call it.
“Okay…” I said, confused.
In front of my place, we hugged goodbye, and I noticed the hug lasted a touch too long. “Did you want to kiss?” I asked him.
“Yes, but I wasn’t sure since I probably won’t see you again since you are returning to the US.” I suppose in one sense he was saying he didn’t want to feel attached. But in another sense, he was saying, “I have no plans to follow up on this.”
We kissed, and it turned into a hot-n-heavy make-out session there on the sidewalk.
Very confusing!!
He walked away towards his car and said, “I’ll text you!”
[Narrator’s voice]: “He did not text her.”
After a full 24 hours of not hearing from him, I texted him against my better judgment to see if he wanted to meet for dinner before I headed to the Milan airport. He waited until it was too late to make plans and said “Sorry I didn’t respond, I was busy.”
I was, yet again, offended at the ghostly communication. Why say “Sorry, I was busy” instead of the more direct “I’m just not that into you”?
A month later, he added me as a friend on Facebook.
Very confusing…
No one will stalk you harder online than a man who was almost interested in you.
“What, gone without a word?
Ay, so true love should do. It cannot speak,
For truth hath better deeds than words to grace it." (2.2.17-19)”
― William Shakespeare, The Two Gentlemen of Verona
After we became friends on Facebook, I sent him a wave emoji by text on WhatsApp. No response. 👻
On TikTok and Instagram, I follow this woman, @ leveluponepercent, who calls herself “Baji,” which means “wise older sister”. She started a match-making service for Muslim Americans and got 20,000 signups in her first month. She is constantly reality-checking her match-seekers through her social media videos. In this one, she talks about “Are we ghosting as grown adults?”
As you’ve heard me say throughout this 2-year dating endeavor, it’s actually easy to let someone know how you feel and your intentions.
And if there’s one thing I’ve had drilled into me through negative experiences, if you have mixed feelings about someone, it’s a no. Both people deserve someone who is fully excited about them. As soon as one person starts thinking “well, they’re not X but I guess I could compromise…” it’s a bad sign. When you meet someone you’re excited about, yes, of course you’ll have to compromise on some things, but not excitement.
So, the moment you realize that you just can’t be as excited as they deserve, you have to tell them, “Hey, I’m just not feeling a romantic connection, but it was nice meeting you.” I typically add a quality I admire about them and tell them that I’m sure they’ll have no problem finding the love they seek. We can be kind to people even if they’re not The One we are looking for.
California
Jovan 9 | Serbian | Mid 30s | OkCupid
A match I’d made in Belgrade, Serbia, within the first few months of starting Romance by Rail, in the Spring of 2024, Jovan 9, messaged me on Instagram around Christmas. We hadn’t met while I was there, but we’d connected on Instagram and sent likes and some messages here and there.
From his photos, he was tall and lean, but muscular. He seemed to be someone who reveled in being a little odd—unconventional. But not too much. I like weird folks more than normal ones, so I remained curious about him.
I’d made an Instagram post on my birthday that I was having a rough day and that my birthday, December 22nd, seemed to be cursed, having experienced all manner of horrific things on this day throughout my life, including a breakup, an earthquake, the end of the world, and most tragically, the death of a dear, beloved family member in 2014.
“Why did you cry all day? If it’s okay to ask as we’re still not offline friends,” he sent me in a DM.
I always thought he seemed like a real one—heartfelt and kind. So I decided to answer him earnestly with a voice note about the horrific thing of Dec 22, 2025 which was that I had been planning to sign a $45,000 consulting contract with a prominent American nonprofit, having gone through rounds of proposal drafts and revisions and the creation of a Scope of Work contract that was ready to be signed, only to have them call me on my birthday to tell me suddenly “nevermind!”
I also shared some reflections about feeling like my Romance by Rail project wasn’t fruitful and about mourning the loss of my fertile years. Also struggles with being home with my family for the holidays and feeling disconnected and lonely in some ways. I went all in.
He responded with a voicenote in kind and several thoughtful text messages—emotionally intelligent ones in which he both held space for what I’d shared and related to the items he felt connected to.
It was a beautiful interaction, and I found him quite physically attractive. And yet…
…something intangible was missing.
He shared that he was still interested in me romantically, and I didn’t move that piece forward. I wasn’t sure. I told him I would probably come back to Europe in the Spring and kept it open. I looked through his Instagram photos again. Def handsome. Def the right amount of weird.
Yuhanna 49 | Indian | Late 30s| Bumble App
I still had 1 week of Bumble premium when I returned to the US. Even though I wanted to wind down the Romance by Rail project, I wanted to see if I could find a good match in the US. I had a week planned in the Bay Area, so I spent some time swiping.
I matched with a South-Asian-looking man who had been living in the US for many years and worked in data analytics. He was attractive and successful. Our messages were pretty good but didn’t enter the realm of flirtation. We tried to plan a date, but I realized I was still recovering from my cold and didn’t have the energy. But maybe I also wasn’t feeling a strong enough spark. Or maybe it’s also just harder to get around in the Bay Area. He was in SF. I was in Oakland. Lots of traffic and crowded public transportation over long distances. It just seemed like too much. I wasn’t up for it.
We didn’t meet, and I headed back to my hometown on a romantic Amtrak train.
He kept texting me every few days to check in, which I liked. EL had gifted me for my birthday a special set of hand-printed Venetian tarot cards. I drew one for me and one for my future lover. My future lover card was “The Beadmaker". “Someone who puts in consistent, sometimes small, effort over time. Consistent in the little things,” I thought. “Yes, I want that.”
Okay, so we should just FaceTime and see, I thought. The worst-case scenario is that I lose an hour. But keep meeting people. You can’t know someone over text alone.
So Yuhanna 49 and I FaceTimed.
It turned out he wasn’t Indian American as I’d thought; he was Indian Indian, having moved to California in his 20s for work. I was curious if there might be a bigger cultural barrier for us, but actually, he seemed quite American.
Physically, he had medium-brown skin, dark hair, and dark eyes that are typical for people from India. He had a short, well-kempt haircut and was wearing a simple zip-up sweatshirt—a combination of both the athleisure and techbro lewks standard to the Bay Area. He was not striking in any way, but was well put together enough. Perhaps what he was communicating the most was that he was just a regular guy.
Our conversation also had a regular-guy-ness quality to it. It was not spicy, not electric, not unusual. We traded facts. Where do you work? Do you like it? How long have you worked there? How long have you lived there? What do you do after work? Who are your friends?
It was an even volley of facts, which I appreciated. I asked, he answered. He asked, I answered. But the connective tissue was missing. There was nothing meaningful drawing us together.
He turned the camera to show me that he was sharing the couch with his dog, a little poodle-mix of some kind. Great regular guy dog. I noticed that his apartment was noticeably tidy with some thriving houseplants. This was probably the most interesting and attractive thing about him so far. I love a man who can nurture a tidy place and some houseplants.
But the second most interesting and attractive thing was that we could talk about current events, politics, and the crazed state of the world. He was well-informed and had all of the correct liberal takes.
And yet, even this part of the dialogue, which could have been filled with passion, fell flat.
After an hour, we wrapped up the conversation. I felt drained.
I made sure to text him within a couple of days and let him know that I wasn’t feeling a strong romantic connection. This is something simple and important we can always do after a first date: let the other person know how we’re feeling fairly quickly. I regret not doing it the next day, actually, but I still did it within a short window, not leaving things hanging.
He checked a lot of boxes: stable job, good-looking enough, intelligent and well-informed on current events, warm pet owner, kind…and I guess that’s why I didn’t text him the day after and lingered on it. Maybe that’s why Giovanni 48 didn’t text me the next day…good but not great connections are confusing. Should we make it work? Should we hold out for something better? How can we be sure we’re not judging too hastily?
I appreciated Yuhanna 49’s consistent checking in, but it fell short of full-on chalance, of Romeo and Juliet-type passion, of Tay and Trav’s dorky enthusiasm.
I was grateful, still, for the brief connection. Good, effortful guys were out there. I just needed to take a break from this quest before trying in earnest again. I needed to find my inner-ness again.
