An Unexpected Love for New York City
4 min read | Jul 2022
Millennial / Conservative / Writer

An Unexpected Love for New York City

When a friend asked me to join her on a trip to New York, I was hesitant. But the hustle and bustle of the Big Apple was electrifying.

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There’s nothing quite like turning a busy street corner onto Times Square for the first time.

Immediately, this sense of awe and surrealism washes over you as you begin to register the larger-than-life billboards and advertisements only ever seen on television and film. The New York Times building seems to stare down at you as you drive by and gawk up at it from inside the tour bus. Flashing lights and sweeping crowds and the frightening driving habits of New Yorkers surround you, welcoming you in what strangely feels like an embrace you were always meant to experience.

As a 30-something introvert who happily lives on a rural Minnesota farm with her husband and cat, I possessed no real desire to travel to New York. But when a friend asked me to accompany her for a milestone birthday trip, I agreed. I didn’t expect to enjoy the trip all that much, but New York City was eye-opening.

At first, I simply hoped that I could make it the whole five days without wanting to crawl up the walls, desperately seeking a little solitude from the bustle of a city whose population outnumbers my entire state’s by about 3 million. But the trip I had such low expectations for turned out to be transformative, awakening an otherwise dormant passion for travel within me.

A young person from the rural Midwest experiences Times Square for the first time.

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Everywhere You Look, There Is Something to See in NYC

Around every corner in the city, we discovered something fun and exciting. Over here, St. Patrick’s Cathedral, surrounded by a convoy of guards cloaked in black, sporting dark glasses and armed with some sort of automatic weapons. Down the street, Rockefeller Center, covered in blooming spring flowers. Over there, the sketchiest massage parlor I’d ever seen nestled against a high-end wine bar.

We spent about an hour in that wine bar, seeing all walks of life traipse in and out onto the New York streets. The bartender was stereotypically trying to make it big as a voice-over artist and podcast host. A scruffy, possibly homeless protester had to be escorted out of the upscale dining area, cardboard sign in tow.

At the bar, a mysterious, dark-haired woman surrounded herself with an array of beverages but sat alone. Judging by her selection of water, tea and white wine, she appeared to be nursing a hangover. Behind her giant reflective sunglasses, she avoided any eye contact and kept mostly to herself—except to snap a photo of my friend and me at the bar. My friend spotted her in the act; she was furious, while I was oblivious to it all. No words were exchanged, and the woman suddenly vanished.

When my friend told me about the photo, I found it absolutely intriguing. Who was this strange apparition? And why in the world did she decide to take our photo—without asking—and then drift away?

With more questions than answers, we turned to the bartender. He told us she was a famous fashion designer, but he couldn’t remember her name and referred to her as Lady Jane. As it turned out, my friend had surreptitiously captured a photo of the woman, so we could try to figure out who she was and what she wanted to do with a picture of us. While we continued on our trip, Lady Jane continued to be a central topic of conversation—not to mention avid Googling. 

As the five-day trip continued, we visited the typical tourist attractions, like the 9/11 Memorial and Museum and the Statue of Liberty. Standing on Liberty Island and facing Manhattan, it struck me that I was actually looking at the New York City skyline; this wasn’t a TV show. It felt surreal. All throughout the trip, I kept thinking to myself, “Holy shit. I’m actually here!”

The Manhattan skyline.

I Needed to Experience NYC to Become Enamored With It

I never understood the appeal of New York City until I visited. Suddenly, I understood just how spectacular it really is. And when the trip was over, much to my surprise, I couldn’t wait to go back. There were so many more places to visit—just thinking of all the wine bars, restaurants, memorials and people-watching we didn’t get to during the trip was enough to make me want to plan annual trips.

Meanwhile, the enigma of Lady Jane continued on for about a year. I constantly wondered who she was. A fashion designer? Merely some eccentric woman with an unhealthy penchant for sneaking photos of complete strangers? I didn’t know.

But the mystery of who she was and why she took our picture was exhilarating. It compelled me to spend hours researching online, trying to match the photo my friend had taken to strangers on the internet. The little puzzle made for an interesting conversation piece on the topic of traveling, leaving me ready to pull out my phone at a moment’s notice to see if a stranger I just met happened to recognize Lady Jane from New York.

Because the bartender and I both had podcasts at the time, he found me and messaged me Lady Jane’s business card. He’d found it while moving and remembered our photo incident. We had our answer: Lady Jane was both absolutely eccentric and a successful fashion designer based on the West Coast. After a year of wondering, the mystery had been solved. Honestly, the mystery was more fun.


Visiting NYC Inflamed My Desire to Travel to New Places

The riddle of Lady Jane was just the cherry on top of a fun, surprising trip. I certainly didn’t expect to fall in love with New York City, but once I felt that undeniable connection, I knew my departure would be filled with a deep longing to return. When I arrived back home to my quiet town in farm country, I was still surprised to miss the abundance that New York City had to offer. It’s an itch that sticks with you until you return, welcoming you with its boisterous streets and the promise of hundreds more Lady Jane characters.

I traveled to New York at the request of a friend, expecting little. I returned home with an emptiness that can only be filled by the discovery of new and unexpected favorite places.

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