Many of you know the basics of how we met — we worked together at an ad agency in New York City. Sherry was the copywriter on the account I helped manage. We first crossed paths while working on a baby commercial she wrote and I helped sell to the client, and the rest, as they say, is history. Below is the play-by-play of our engagement, told from both of our perspectives.
SHERRY: We love to reminisce about meeting and falling in love in New York, but after a while it became clear that neither of us imagined living in Manhattan forever. The city’s constant hustle, long work hours, and stress were cutting into our time together. I reached a point where I was ready to leave, and when I told John “let’s get out of here,” he was eager too. But where should we go?
JOHN: I suggested moving to Virginia — warmer, calmer, and greener. Sherry agreed instantly, which made me realize how serious we were. We chose Richmond because my sister lived there, the city had an artsy, metropolitan edge, and there was a decent advertising scene so we might find work. Deciding together to quit our jobs, find a new apartment, and move in together forced us to evaluate the future of our relationship. It had only been about six months, but we both felt certain this was long-term. I decided to propose to Sherry before we even left New York, and we posed for a few clichéd New Yorker photos in front of the skyline before driving off.
SHERRY: I had a feeling John would propose eventually — we’d had honest conversations about our future — but I didn’t know when. I wasn’t in a hurry, and the suspense was part of the excitement. I probably wouldn’t have moved without some confidence that marriage was likely in our future, so I reveled in the anticipation that it might happen when I least expected it.
JOHN: I actually bought an engagement ring before we left the city, after getting hints from Sherry and advice from her best friends. But I didn’t want to propose while I was unemployed, so I waited until I had steady work. We moved to Richmond on February 25, 2006, and I carried that ring in my pocket the whole time. During our going-away party in New York, Sherry posed with a coworker who had helped me pick the ring — one more reminder that I was getting closer to asking the question.
SHERRY: Our first weeks in Richmond were exciting. I started freelancing as a copywriter from home while John hunted for a job. Naturally, family members began asking when we would get engaged. Some guessed it might happen on my birthday, March 19th. I didn’t push for it, but I was excited by the possibility.
JOHN: I hadn’t planned to propose on her birthday. I wanted to wait until I had a job lined up and a good plan. I had imagined proposing on a summit in the Blue Ridge Mountains — a perfect “welcome to Virginia” moment. Coincidentally, my cousin and sister invited us to hike that peak the day before Sherry’s birthday, March 18th. That seemed like the right time.
SHERRY: The hike was challenging — nearly six miles with plenty of rock scrambling. Being short, I sometimes needed help getting up taller rocks. John joked later that he really made me work for my ring. For me it was just a fun, tiring day; I was thrilled to reach the summit and happy the hardest part was over.
JOHN: Once I landed the job, everything fell into place. I asked Sherry’s parents for their blessing during a hectic stretch when her mom and stepdad were leaving on a cruise. I left messages and emails and hoped the replies would be positive. I told my own parents too, and even if I caught the answering machine, I felt supported. With approvals in hand, I slipped the ring into my camera bag and packed it with trail supplies, waiting for the right moment.
SHERRY: At the summit, our group joked and shuffled about. John insisted we take some photos together, our usual self-portrait style with his hand as the tripod. The camera “died,” so he went to fetch new batteries. I warmed up with a few jumping jacks while he dug in the bag.
JOHN: The “dead” camera was my excuse to reach into the bag. I pulled out the ring, knelt, and asked, “Sherry, will you marry me?” She stopped mid-jumping-jack, ran to me, and jumped into my lap. We hugged, she said yes, and we kissed as other hikers passed by. It was a simple, perfect moment.
SHERRY: After a few breathless minutes, John’s cousin and sister emerged, and we celebrated with hugs and photos — the camera was fine after all. On the descent, strangers congratulated us and even high-fived us. Then, to our surprise, John’s parents appeared — they had known the time and place and quietly made their way to the trail to share the moment. That unexpected cameo made the day even more special.
JOHN: We finished the outing with an easy lunch at a small restaurant in Sperryville. It wasn’t fancy, but it felt right. In the days that followed we called family and friends and sent an announcement email. Former coworkers who didn’t know we were dating were delighted and surprised. The mountaintop proposal was simple, heartfelt, and exactly what we wanted — an intimate beginning to the next chapter of our lives together.
So that’s our mountaintop engagement. We’d love to hear your stories too — where did you get engaged, how did it happen, and did you know it was coming?