Photo by Bridget Samuels

“Uptown or Downtown? UPTOWN OR DOWNTOWN??” Mark sputtered, drowning out the Oasis tape in my little red Honda, as he downshifted to take the curve. My spiral-permed hair fluttered in the breeze as I flicked a Marlboro Light out the window. We had just popped out of the Holland Tunnel – Manhattan side – and had to choose our destination, fast.

Five hours earlier Mark had pitched the idea in a Kwik Fill parking lot. “Wanna go to New York City?” he had asked as his 6’2” frame maneuvered into the driver’s seat of my ‘94 Civic, two fresh Mountain Dews in one hand. I owned the car – a 16th birthday gift in a town where a brand new Honda seemed lavish – but Mark always drove it. It was unspoken that he, age 22, was the grown up.

He handed me a 20 ounce green bottle, already dripping with condensation in the hot August air, and waited for my answer. We lived almost 300 miles from the City, and it was 9PM already. Neither of us had ever been there. We didn’t have a plan, or a map, or a GPS, or a cell phone. Our collective net worth was in the low three-figures, and credit cards were for adults, not country kids like us. It was a ridiculous idea.

Naturally, I said “yes” faster than I could uncap my Mountain Dew.

The night had started out like any other, Mark behind the wheel, aimlessly driving without a destination. But summer was almost over, which meant our nights together were ending, too. In a few weeks I would leave for college. Mark would stay at home, laboring on the farm where he had worked since high school. I should have been excited to leave town for good, but I wasn’t ready for a life where Mark wasn’t always sitting at my left, in charge of my next destination. We needed more time together and ten round-trip hours in a car could be time well spent. Maybe we would fuse to the seats and I’d never have to leave him.

Five hours later we emerged from below the Hudson River, confronted with signs and a sudden decision: Exit 2 for Uptown, or Exit 3 for Downtown?

“Uptown!” I shouted, because Billy Joel wouldn’t have sung about an Uptown girl if it wasn’t a nice place to visit. With that sound logic as our guide, we headed north, overshot the Uptown I imagined, and drove straight into Harlem.

It was 2AM, and we were lost in the scariest place I had ever seen. Each new block looked more daunting than the last. Industrial garage doors covered the store fronts; windows were boarded and barred. Graffiti was everywhere, haunting the deserted streets. Everything was dark. Everything was closed down and locked up. Where was the City That Never Sleeps? Where was the sparkly ball? Where were Christie Brinkley and the other Uptown girls?

We found an open gas station and Mark went inside. Would he be okay in there? Would I be okay out here?? I didn’t know the answers. I only knew that the City was terrifying, and we had no business being in it.

I don’t know what we expected when we got on the highway that night, me in my flannel shirt and braces, he in his Levis and work boots. I don’t know what we thought we would do, or where we thought we would sleep, without credit cards or cash. I had a new college checking account – opened with a $100 deposit from my mom – but we had already spent half of it on gas and Mountain Dew. We were so excited by the journey that we forgot to consider what we would do when we reached our destination.

A kind New Yorker in the Shell station pointed Mark toward home, and we got off the island as fast as my little car could take us. It wasn’t until 5AM, with the City a safe distance behind us, that we pulled off to sleep at the only place we could afford: my little red Hotel Honda.

Two weeks later, I left Mark for Syracuse University. Just months after that, Mark left me with a broken heart. With nothing holding me back, it was time to figure out where I wanted my life to take me – or better yet, where I wanted to take my life.

Although it took years to figure out my ultimate destination, eventually I took my life back to the scary city with all the graffiti, for good. This time, I found my way to the Uptown I had imagined. Half a lifetime after that first New York road trip, I am a devout Upper East Sider, and even head north to those same Harlem streets that once seemed so scary. They have changed. And so have I.

Jules Barrueco is an attorney and a writer in New York City. She lives in the Upper East Side with her husband and their rescue dog, Tuck Noodle. Follow Jules on Facebook or at www.julesbarrueco.com.