Revisiting My Lost Love: New York City, A Lifetime Later

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Her collection of meticulously arranged photographs—a vintage sepia truck, a fox donned in a suit, a striking black-and-white shot of a wheat sheaf—tease me from the walls of her charming Brooklyn apartment. These images, alongside her extensive library of classic literature and an impressive assortment of vintage vinyl near an old turntable, seem to whisper the same silent message: Look closely. This is the path you never took.

During a recent business trip, I found myself strolling through the picturesque back streets of her Brooklyn neighborhood with my high school friend and her companions. She animatedly highlighted the unique details of the homes, restaurants, and the rich history embedded in the architecture. They reminisced about shared adventures at various bars and pubs, each story steeped in laughter and nostalgia. It was difficult to hide my envy.

Fifteen years ago, in my early twenties, I was eager to move to New York without even seeing it first. The city called to me like a misfit drawn to a circus. At the end of my college years in 2000, still rooted in my Midwestern hometown, I shared with my boyfriend my ambition to apply for an internship at CBS in New York. We both pursued the same major, and he encouraged me. He landed the internship; I did not. But I went to New York that year anyway, filled with equal parts excitement and anxiety. Those hard city streets left my feet sore, but my heart was aflame with possibility.

New York was everything I had imagined and so much more. Each visit fueled my imagination; I pictured myself living in various neighborhoods, exploring potential homes, and scanning job postings. Yet, I never let myself truly consider making that leap. As a naive 23-year-old, fear held me hostage.

Loving New York was akin to crushing on someone completely out of reach. The yearning was unbearable. Eventually, I began to focus on the city’s downsides—its steep cost of living, overcrowding, and perceived dangers—convinced myself that it wasn’t what I truly wanted, all to shield my heart from the possibility of rejection. I told myself that wanting to move to New York was a foolish dream.

Like that unattainable crush, I let the idea of New York slip from my mind. In the decade since my last visit, I married, transitioned from one career to another, had two kids, purchased two homes, lived in two different cities, and began anew after escaping an abusive marriage. My high school friend has thrived in New York City since the moment I decided to abandon my dreams of living there. Over the past 15 years, she has built a successful career, developed a vibrant social circle, and traveled the world, all while feeling truly happy. Each night, she falls asleep embraced by my old infatuation: this magnetic city. Listening to her tales of city life made my envy grow.

In those two days with her, I felt as though I had stepped into a modern rendition of It’s a Wonderful Life. I was confronted with an alternate version of my life—one I could have lived had I not let fear dictate my choices. If only I had been brave enough to pursue a love that could have transformed my life, perhaps I too would be enjoying weekends “leaf peeping” while antiquing in Connecticut and taking business trips to China. Maybe I wouldn’t be navigating a challenging divorce or raising my children as a single mom.

Perhaps it took time to learn that a broken heart isn’t the worst fate; rather, it’s a heart that remains unfulfilled that truly aches.

After a delightful dinner with her friends, I confided in my old friend about all the things I admired about her life. We stumbled along the streets, tipsy from cocktails, and she confessed that while she loved her life, something felt amiss. Her friend echoed this sentiment, sharing the daunting reality of connecting with others in a city like New York, where finding a comparable match among millions can seem impossible. I hadn’t realized until that moment I had spent the evening with three intelligent, attractive women, all still searching for love. It turns out New York is everyone’s cherished lover, and the prospect of finding another can feel less appealing.

The following day, I wandered the city alone during a break from my conference, reflecting on the lives we lead—hers, mine, and the one I didn’t choose. At an intersection, I simply followed the “go” signal, walking for an hour while pondering life’s many paths. I can’t claim to have found closure or absolution at the end of that walk. I simply recognized that we each walk the path we are brave enough to follow at any given moment. Maybe it’s about accepting the route that presents itself with a “go” signal.

If you can find joy along the journey, you’re doing well. If you can look back and say, “I did my best,” and look forward with the hope of trying again tomorrow, that’s what truly matters—regardless of your zip code, relationship status, or how many carefully curated photos adorn your walls. The essence lies not in the surroundings but in the connections we foster and the love we nurture within those spaces.

For further insights on navigating relationships and family life, check out our other blog post here. If you’re considering starting a family, reputable retailers like Make a Mom offer excellent options for at-home insemination kits. Additionally, you can find more information on the topic of artificial insemination at this Wikipedia page.

In summary, our lives are shaped by the choices we make, the paths we take, and the love we allow ourselves to experience. Embrace the journey, cherish your experiences, and remember that happiness is not defined by a specific location but by the connections we create.


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