Washington, D.C., is, to date, my greatest failure. My Waterloo. More aptly, perhaps (if you want to remain on the firm soil of American history), my Bunker Hill. 

To those unlike me, D.C. isn’t a site of lost opportunities, but instead stands tall as the capital of the free world — a shiny beacon of white, pristine hope, symbolic for those wishing to flee from tyranny and seek out more fruitful pastures. Even in the face of multiplying criticisms and America’s perceived antagonism in the arena of world politics, millions around the globe still look upon the city’s magnificent landscape and see the representation of lofty achievements and dreams that can be accomplished from very little — or, more often, nothing — returning their longing gaze. D.C., with its air of inherent optimism, is many things to many people.

But to me, it represents failure.

No, I’m not concerned about the uncertain swampland of its foundation, nor plagued by its notoriously oppressive summer heat; it’s not even the inadequacies of the fumbling judicial system that leave me feeling on edge. Rather, it’s the fact that I’ve been to this city-state four times and have yet to actually see or set foot upon anything touristy, noteworthy, historically significant, or otherwise. The Capitol Building? Washington Monument? White House? Nope. On four consecutive occasions, these tributes to democracy have eluded me with the swift, lethal precision of a top-tier CIA agent.

The first time I ventured forth into the District of Columbia was in eighth grade, when a seriously flawed plan to send 200 suburban Detroit middle-schoolers to Washington, D.C., for only one day was conceived and executed. Over the course of a single 18-hour period, every member of Anderson Middle School’s eighth-grade class piled into a charter flight, which appeared to be on par with the Wright brothers’ plane in terms of safety features, and set forth, bound for our nation’s capital. Upon landing, we spent the day learning what the district looked like from the inside of a tour bus, whizzing along at 70 miles per hour. For an uncommonly generous allotment of 45 minutes, we were allowed to teeter on the edge of Arlington National Cemetery, which was, on this particular day, roped off and closed to the public, due to an elaborate military ceremony which would probably have been interesting to watch, had we been allowed within 80 feet of it. Without any historical context for the site or ceremony imparted upon us by our chaperones, we let our inquisitive eyes fall over the closed gates, and the agenda pressed onward.

The next stop on our itinerary, naturally, included a quick interlude for some regional food at Taco Bell, followed by four hours of sitting in the lobby of the Smithsonian, waiting for the chaperones to regroup and, more than likely, figure out how to cast their charges as liars when the story of their ineptitude eventually made its way back to the parents. By the time we flew back to Detroit that evening, I was already drafting a complaint letter to my congressman about the abysmal state of public education in this country.

So it was that inaugural foray into D.C. that set the precedent for repeated disappointments. I returned to Detroit feeling angry, frustrated, deceived; utterly betrayed by what was supposed to have been a whirlwind tour full of sightseeing and wonder. As a child, I had grown up worshipping the aura of D.C.: Both of my parents were — and still are — active political junkies, and my little brother and I lived in a household where MTV was forbidden, but the personalities on Capitol Hill and National Public Radio were revered as demigods. From the time I could start stringing sentences together in my mind, I idolized political nerd-icons like John Adams, Thomas Paine, and especially the man on the money, Benjamin Franklin. In school, I continually impressed my teachers and befuddled my classmates with my ability to drop names like Newt Gingrich and Walter Mondale into casual conversation.

Washington, D.C., was therefore something I felt entitled to. It was always supposed to be mine — setting foot upon the same city where so many great leaders had lived and governed was not just my privilege, but my God-given right. Yes, to my 12-year-old self, I had been endowed by my creator with certain unalienable rights, and the most valuable of these was to visit D.C. — I was the girl who would have far preferred the license to vote over that to drive.

Years later, putting aside my battered feelings of rejection, I decided to attempt a calculated foray into D.C. again at the age of 21, but this time, on my own grown-up, self-mandated terms. My second trip to the District took place during the summer of 2006, when I traveled by Amtrak to visit a close friend who was working in the city for the National Breast Cancer Coalition as an unpaid intern. Seeing as how summertime in D.C. is about as climate-friendly as a hot tub on Mercury, we could barely manage to coax our sweat-stained flesh out of bed each morning, let alone go out and see the sights. Alas, my desperation to traverse hallowed ground could not match my lust for the arctic blast of air-conditioning. The closest encounter I had with an authentic D.C. experience occurred when Danielle, my friend’s ultra-right-wing roommate (for whom Hitler would not have been conservative enough), participated in a number of antagonistic staring matches with my Seven Sisters college-attending, rugby-playing, woman-loving friend. These showdowns happened while Danielle was in the midst of preparing to go see Sean Hannity deliver a speech — although, according to Danielle’s plaintive whines, poor Sean’s political views just didn’t make the “conservative enough” cut. (Perhaps he and the Führer could have, in an alternate universe, commiserated over beers together.)

Trip number three to D.C. only served as a stopover on the way to New York City. As I watched its tantalizing skyline rush by through the tinted windowpane of a Chinatown bus, I shook my head in disbelief that my favorite city — by proxy — was yet again slipping through my fingertips. It was like digging through an overflowing goldmine and not being able to clasp the riches within the clench of my palm. Another gold rush, vanishing into the horizon like a dreamy, beautiful mirage. I was an eager miner without a prayer.

Trip number four occurred on Groundhog Day, 2008, just after Punxsutawney Phil disappointed millions by seeing his shadow and thus selling far fewer novelty beer steins than usual. The purpose of this fourth and as yet final trip was to see two of my favorite stand-up comedians — Michael Ian Black and Michael Showalter — perform live on a double bill at a historic synagogue on I Street. While I have yet to set foot on Capitol Hill or see the likeness of the Lincoln Memorial depicted on anything other than a snow globe, I am proud to say that the historic — it’s historic! — I Street Synagogue has felt the tread of my foot and has been absorbed by my tourist’s eye. And while the evening ended on a decidedly happy note, I could not help but pay acknowledgement to the familiar sensations of disappointment and loss that always seemed to accompany any association I might have with the city itself. Yet again, I had approached the heart of D.C. only to be turned out at the last minute — an outcast lost among insiders. Perhaps it was my lot to be a continual immigrant — not crossing from one country to another, but still hoping against hope to slip through the invisible threshold undetected. For the fourth time in my scant 23 years on earth, I had found myself on the wrong side of the deportation proceedings.

Washington, D.C., has thwarted my efforts of exploration four times. Each journey leaves me feeling unfulfilled, wasted, and spent, but yet I continue to remain completely enthralled by the city’s imposing presence. It has failed me as much as I have failed it, but I somehow manage to abide by a strange sense of optimism, in the hopes that one day I will achieve my American dream and conquer the mystical city. Someday, I will make the long-overdue pilgrimage to reclaim what is mine — what has always been mine since the days of my childhood. Modern America may sport a reputation for brutish arrogance and impatient action, but perhaps those who judge us as hotheaded have forgotten that nearly a decade elapsed before independence was obtained from Britain. If our founding forefathers could wade through indecision, treason, war, and suffering, then surely I can remain faithful until the District is ready to embrace me.

These days, whenever I encounter D.C.’s iconic image, emblazoned with hope before my eyes, I turn eastward and punctuate the atmosphere with my determined fist, saying “You will be mine. Someday, you will be mine.”

In The Fray is a nonprofit staffed by volunteers. If you liked this piece, could you please donate $10?