Our Unforgettable Engagement Story: A Journey from NYC Skyscrapers to Blue Ridge Peaks

Every great love story has a unique beginning, and ours started amidst the vibrant, fast-paced world of New York City’s advertising scene. It was a dynamic environment where creativity and deadlines often collided, and where, unbeknownst to us, our paths were destined to intertwine. I (Sherry) was a copywriter, crafting narratives and slogans, while John was instrumental in managing the account I worked on. Our professional collaboration blossomed into something truly special, ignited during the creation of a memorable baby commercial. I penned the script, and John expertly guided it through to client approval. The rest, as they say, became our personal history. (And yes, for those wondering, that’s Becki Newton, now celebrated for her role on Ugly Betty, in that very commercial!).

The Big Apple Farewell: Trading Skyscrapers for Serenity

New York City had given us so much – incredible experiences, professional growth, and ultimately, each other. We cherished our time reminiscing about the early days of our relationship, falling in love amidst the iconic cityscape. However, as our relationship deepened, a quiet understanding began to emerge: Manhattan, for all its magic, wasn’t our forever home. The relentless hustle and bustle, coupled with the ever-increasing demands of our long-houred advertising jobs, began to wear on us. Our precious quality time together started to dwindle, making us question the sustainability of our city life. We both realized we had enjoyed the NYC experience to its fullest; John, after two years, was already yearning for a change of scenery, and after more than six years, I (Sherry) was slowly, but surely, arriving at the same conclusion.

One evening, I approached John and uttered the words he later confessed he was “dying to hear”: “Let’s blow this pop stand.” It was a momentous decision, a collective sigh of relief, but it immediately brought forth a new, exciting question: Where would we go? John, ever the advocate for his roots, enthusiastically suggested his home state of Virginia. He painted a vivid picture of its warmer climate, its calmer pace, and its lush, green landscapes. My immediate, unhesitating agreement (in less than a second!) only solidified for both of us that this was far more than just an average relationship. This was a partnership built on shared dreams and a willingness to embrace new adventures together.

We ultimately settled on Richmond, Virginia. The decision was multifaceted: John’s sister resided there, it boasted an appealing artsy and metropolitan edge, and crucially, it had a robust advertising presence, offering us a fighting chance to land new jobs upon our arrival. This period of joint decision-making – to quit our stable careers, embark on a daunting apartment hunt in an unfamiliar city, and announce to our families that we were moving in together – acted as an undeniable catalyst. It forced us to confront the seriousness of our commitment and whether we were truly in it for the long haul. Although we had only been dating for about six months, we both felt an unwavering certainty that this was “for keeps.” It was during this whirlwind of life-altering choices that John made a profound personal decision: he would propose to me, even before we bid farewell to the city that had brought us together. And so, with our future unfolding before us, we posed for a few quintessential “bad-ass New Yorker” photos against the iconic skyline, savoring our last moments before heading south.

The Ring’s Secret Journey: From NYC Plans to Richmond Reality

The thought of marriage wasn’t entirely new to me. John and I had always maintained open and honest discussions about our future, so I was fairly certain a proposal was on the horizon at some point. However, the exact timing remained a mystery, and I wasn’t in any particular rush. I relished the excitement of knowing it was coming, a quiet confidence that undoubtedly played a part in my willingness to embark on such a monumental move. I often found myself pondering when it might happen, usually concluding it would occur precisely when I least expected it.

Meanwhile, John, with a secret mission underway, was already making preparations. Guided by subtle hints from me and invaluable advice from my best friends, he managed to acquire an engagement ring before we even departed New York City. Yet, despite having the ring, the timing didn’t feel quite right. With so many variables in flux – primarily, the bold move of quitting his job without a new one firmly secured – he felt it would be more appropriate to ask for my hand once he was gainfully employed again. So, on a chilly February 25, 2006, we packed our lives into a minivan and journeyed to Richmond, Virginia, still boyfriend and girlfriend, with that beautiful, sparkly ring “burning a hole in John’s pocket.” The anticipation, for both of us, was palpable.

Before leaving, we celebrated our new chapter with a going-away party in NYC, surrounded by friends and colleagues. One of those colleagues, Heather, was actually one of John’s trusted “ring advisors” – a fact I wouldn’t discover until much later. Her knowing smile in our farewell photos now holds a special meaning, a silent testament to the secret plans unfolding behind the scenes.

Richmond Rhythms and a Birthday Surprise

Our initial weeks in Richmond were a whirlwind of excitement and adjustment. I embraced a new path as a freelance copywriter, allowing me the flexibility to work from home and explore our new surroundings. John, on the other hand, was diligently pounding the pavement, seeking a new professional opportunity in downtown Richmond. Despite the fresh start and new routines, a certain unspoken question lingered in the air. I was almost certain John had the ring, and my family, bless their hearts, were not shy about their conjectures. Several “pushy family members,” as I affectionately recall them, were quite vocal about our decision to move in together without being betrothed. They frequently guessed that a proposal might coincide with my upcoming birthday on March 19th.

John, however, had no intention of proposing on my birthday itself. His plan was strategically linked to securing a new job – he had several promising interviews and was simply awaiting the definitive call. Once employed, he envisioned crafting the perfect, elaborate proposal. He had a particularly romantic idea: to pop the question at the summit of one of his cherished hiking spots in the majestic Blue Ridge Mountains. It felt like a quintessential “welcome to Virginia” moment, a symbolic exchange of skyscrapers for mountains, echoing our journey. Imagine his surprise, then, when his cousin and younger sister spontaneously invited us to join them for a hike up that very peak – Old Rag Mountain – on March 18th, the day before my birthday. The universe, it seemed, was aligning with his secret plans, albeit a day earlier than anyone (except perhaps the universe itself) might have anticipated.

The Clock Ticks: A Job, a Hike, and Secret Phone Calls

Our early days in Richmond meant we were practically inseparable. With me working from home and John awaiting a job offer, he had precious little alone time for clandestine conniving and elaborate proposal planning. This intense togetherness, however, was about to change. Just a few days before my birthday weekend, the phone call John had been anxiously anticipating finally came: he had landed a new job at a Richmond ad agency! It was a truly happy day. I was absolutely thrilled for him; I had witnessed his growing anxiety and relief washed over us both. This pivotal moment not only brought professional stability but also, unbeknownst to me, set the final wheels of his proposal plan into motion.

With his new job secured, John could finally put his long-held proposal plans into action. He had the ring, the hike was spontaneously scheduled for the perfect location, and now, the last crucial step: asking my parents for their permission. This wasn’t a simple task, given my near 24/7 presence by his side, and the added complication that my mom and stepdad were embarking on a cruise mere hours after he received his job offer. Seizing a rare window of opportunity during a work call I was on, John ingeniously managed to leave messages for both my mom and my dad. My mom later returned his call, leaving a voicemail filled with enthusiastic approval and excitement (John couldn’t pick up as I was in the car with him). My dad’s response was equally clear, though wonderfully terse: an email containing just a single character – an exclamation mark (“!”) – which John rightly interpreted as a resounding “yes.” He later learned my dad’s brevity was due to fear that I might accidentally see the message! The very last item on John’s pre-proposal checklist was to inform his own parents. He snuck in a phone call later that day, but fate, or perhaps luck, had it that he reached their answering machine.

The Master of Diversion: A Tire Story and a Secret Hike

Completely oblivious to John’s intricate pre-proposal phone calls, I thought nothing of it when he received a seemingly random call from his dad that afternoon. It probably should have been a clue when John nervously exited the apartment to continue the conversation outside, but he was a master of diversion. He expertly covered his tracks with a convincing story that his dad was offering advice about a car tire question we had been discussing earlier. When I peeked out the window, he was convincingly bent over, inspecting the tire while on the phone. In fact, I was so utterly convinced by his sly little cover-up that as we lay in bed that night, I kept asking if he thought the tires were genuinely okay. This particular detail, to John’s endless amusement, still sparks laughter between us to this very day.

John was confident his “tire-diversion” had worked flawlessly. More importantly, he was immensely relieved and pleased to hear his parents share in his excitement for his proposal plans, now set for the upcoming Saturday. They were absolutely thrilled at the prospect of welcoming me into the family. With all his covert arrangements in place, he spent the next couple of days in anxious anticipation, waiting for Saturday, March 18th, to finally arrive. When it did, he carefully snuck the ring box into our camera bag and then packed it discreetly into his backpack, alongside our water bottles, trail mix, and other standard hiking supplies. The stage was set for an unforgettable adventure.

Old Rag Mountain: The Hike for a Ring

I woke up that Saturday morning incredibly excited about our hike, even if the air was a little crisp. Joining us were John’s cousin Travis and his sister Carrie, along with her boyfriend. It felt like a perfectly normal, enjoyable outing, so I focused all my energy on simply relishing the hike. Old Rag Mountain, for anyone who has experienced it, is notoriously challenging. It’s an almost six-mile trek, involving a significant amount of strenuous rock scrambling. I often joke that John truly made me work for my ring – and trust me, I’m not exaggerating about the rocks!

John, meanwhile, had already briefed our fellow hikers on his grand plan: reach the mountaintop, enjoy lunch, and then discreetly make themselves scarce so he could execute his proposal. However, his companions seemed to have gotten those last two steps slightly muddled. The moment we crested the summit, everyone immediately vanished! John, who hadn’t mentally prepared for such an abrupt exodus, found himself in an awkward scramble. He had to chase after them, whispering frantically that “eating together was first on the agenda.” I definitely noticed something peculiar about their hushed exchange, but thankfully, it didn’t completely blow his cover. The mystery only added a subtle layer of intrigue to the already exhilarating experience.

The Unexpected Turn: “Dead Camera” and a Dropped Knee

From my perspective, I just chuckled to myself, thinking I’d missed an inside joke or something. What truly mattered was reaching the top of the mountain; I was utterly exhausted from the challenging ascent. Being quite short, there were sections where I literally had to be hoisted up tall rocks by two people – one pulling from above, one pushing from below – as my limbs simply weren’t long enough to manage it solo. But after a well-deserved rest and some refueling, I was more than ready to get back to hiking, especially anticipating the downhill trek that awaited us. It was also quite chilly at the summit, so movement was definitely appealing. I was therefore a bit caught off guard by John’s insistence that we snap a “bunch of pictures” before leaving, but I happily played along. After all, the scenery was breathtaking, and after all that climbing, it made perfect sense to soak it all in. We decided to take a self-portrait together, a favorite ritual where John’s extended arm cleverly serves as a makeshift tripod. As we posed for our usual snapshot, a sudden, frustrating message appeared: “Camera died.” Ugh. But John, ever calm, reassured me that we had more batteries in the bag.

Little did I know, the “camera dying” was not a technical malfunction but a perfectly executed maneuver. John hadn’t pressed the shutter button; he had intentionally pushed the “off” button. This was all part of his ingenious plan, a pretext to delve into the camera bag to retrieve “new batteries” – and something far more precious. As he knelt down, ostensibly to fish out the camera’s power source, he instead reached for the hidden ring box. Spinning back around, he was suddenly on one knee, the ring box propped open, displaying a dazzling symbol of our future. “Sherry,” he simply asked, his voice filled with emotion, “will you marry me?” My spontaneous jumping jacks, a comical attempt to keep warm, came to an immediate, stunned halt.

Yes! The Mountaintop Celebration

I was in complete and utter shock. The world seemed to pause. All I remember is freezing mid-jumping-jack, my body momentarily suspended in disbelief, before I instinctively ran over to John and practically leaped into his lap, still kneeling there on the mountaintop. With me cradled in his lap, John gently reminded me, with a loving smile, that I needed to actually say “Yes” to make it official. And of course, I did. We shared a heartfelt kiss, tears welled in my eyes, and for a few blissful moments, we were lost in our own world, completely oblivious to the random hikers who occasionally traipsed by. It was, in every sense of the word, perfect.

After several minutes of basking in the glorious, just-engaged glow – a feeling I still couldn’t quite believe was real – we emerged from our secluded lookout point. We were immediately greeted by John’s sister and cousin, who had been patiently waiting with bated breath, their faces etched with anticipation. I choked out the wonderful news, and a flurry of hugs, happy squeals, and enthusiastic picture-taking ensued. The camera, it turned out, was miraculously *not* out of battery after all! John’s cousin Travis even managed to snap a truly candid gem of a photo, capturing us kissing joyfully in the background, his own face a picture of delighted mischief.

A Descent of Joy and Unexpected Encounters

The walk down Old Rag Mountain, now as an engaged couple, was undeniably the best hike of our lives. The earlier chill and the fatigue in our legs were entirely forgotten, replaced by an intoxicating sense of euphoria. John’s sister, Carrie, was so overcome with excitement that she enthusiastically exclaimed to every passing hiker, “They just got engaged!” Strangers offered high-fives and heartfelt congratulations as we descended, our faces beaming with permanent smiles. Then, amidst the well-wishers, a pair of hikers approached who looked vaguely familiar, sparking a flicker of recognition.

When I finally recognized John’s parents walking up the trail towards us, I was utterly speechless. My mind immediately raced, believing John had orchestrated this entire, elaborate surprise. But then I looked at his face and realized he was just as genuinely surprised as I was! His parents, having been clued into the approximate time and location of the proposal, decided to surprise us both by hiking up the backside of the mountain to intercept us on our descent. They cautiously approached, asking, “Any news?” before erupting in joyous congratulations. I suppose in my shock and excitement, I had completely forgotten to flash my dazzling new ring!

And so, our incredible hiking excursion concluded with John’s beaming parents joining us. After reaching our cars, they treated us to a second lunch – all that walking had certainly worked up an appetite! – at a charming, unpretentious “hole-in-the-wall” restaurant in nearby Sperryville. It was far from a fancy, storybook first post-engagement meal, but we absolutely adored it. To this day, we still fondly reminisce, “Aww, remember that lunch in Sperryville?” I was particularly grateful that his parents suggested it, as I realized, with a touch of humor, that my elaborate proposal plans hadn’t really extended much beyond the actual popping of the question itself.

The Big Reveal: Rocking Worlds and a Future Unveiled

After lunch, I was still utterly stunned and couldn’t stop smiling from ear to ear. I vividly remember calling friends and family, eager to share our monumental news. My mom, still enjoying her cruise, had to wait a few days for the exciting update. A couple of days later, we crafted and sent out an email announcement to literally everyone we knew. This included all of our former coworkers back in New York, many of whom had absolutely no idea we were even dating! While it wasn’t technically against company policy, we had intentionally kept our relationship under wraps to ensure it didn’t impact our professional dynamics. Needless to say, the reactions were priceless. Within minutes of hitting ‘send,’ our phones were buzzing with about thirty conference calls from people screaming with disbelief, exclaiming they “had no idea” and dramatically claiming we had “rocked their world.” It was a fitting, energetic reaction, especially considering the playful email announcement we sent out:

And so, that is the complete tale of our mountaintop engagement – a journey filled with covert planning, unexpected twists, and an abundance of joy, all set against the stunning backdrop of the Blue Ridge Mountains. We’re sure many of you have equally exciting, complicated, and unforgettable stories to tell. We would absolutely love to hear the details about yours: Where did it happen? How did it unfold? Did you have any inkling it was coming? Share your amazing love stories with us!