Many of you know the basics of how we met — we worked together at an advertising agency in New York City. Sherry was the copywriter on an account I helped manage. We first crossed paths while working on a baby commercial (she wrote the script and I sold it through to the client), and the rest, as they say, is history. So here is the play-by-play of our engagement, told from both the proposer’s and the proposee’s perspectives.
SHERRY: We love to reminisce about how we met and fell in love in NYC, but after dating a while it became clear neither of us saw ourselves living in Manhattan forever. The city’s nonstop pace and long work hours began to cut into our quality time, so we decided we’d had our fill. John had been itching to leave after two years, and after six years I was coming to the same conclusion. I told John the words he later confessed he had been dying to hear: let’s blow this pop stand. But where should we go?
JOHN: When Sherry said she was willing to leave Manhattan, I suggested my warmer, calmer, and greener home state of Virginia. She agreed immediately, and that made me realize this was more than an ordinary relationship. We chose Richmond because my sister lived here, it still had an artsy metropolitan edge, and there was an advertising presence that gave us a chance at work. Deciding together to quit our jobs, find a new apartment, and tell our parents we were moving in together forced us to evaluate whether we were in this for the long haul. It had only been about six months, but we both felt certain. I decided to propose before we even left New York City. We even posed for a few New Yorker-style photos in front of the skyline before heading out of town…
SHERRY: I suspected John would propose someday because we’d had honest discussions about our future, but I didn’t know when — and I wasn’t in a rush. I liked the surprise and the thought that it would likely happen when I least expected it.
JOHN: Following hints from Sherry and advice from her friends, I bought an engagement ring before we left the city. But with so many uncertainties — quitting my job without a new one lined up — it didn’t feel right to propose until I was employed. On February 25, 2006 we moved to Richmond as boyfriend and girlfriend, while the ring stayed in my pocket. Here’s Sherry with our coworker Heather (one of my ring advisors) at our going-away party in NYC.
SHERRY: Our first weeks in Richmond were exciting. I became a freelance copywriter working from home while John hunted for a job in downtown Richmond. Still, there was a looming question — did John have the ring? Family members kept asking when he would propose, and some guessed it might happen on my birthday, March 19th.
JOHN: I hadn’t planned to propose on her birthday. I was waiting to secure a job and then plan the perfect proposal. I liked the idea of asking at the summit of one of my favorite hikes in the Blue Ridge Mountains — a fitting “welcome to Virginia” moment. Imagine my surprise when my cousin and sister invited us to hike that exact peak the day before her birthday, March 18th.
SHERRY: In those early Richmond weeks we were nearly inseparable, so John had little chance to plan secretly. A few days before my birthday he got the call — he landed a job at a Richmond ad agency. I was thrilled for him.
JOHN: With the job secured I put my plan into motion. I had the ring, the hike was set, and next I needed Sherry’s parents’ blessing. That was tricky because she was with me most of the time and her mom and stepdad were leaving on a cruise. During a work call Sherry was on, I left messages for both her parents. Her mom returned the call and left an excited voicemail; her dad sent a single character email — “!” — which I took as approval. I also tried to call my parents but got the answering machine.
SHERRY: I had no idea John was making those calls. Later, when he took a phone call from his dad and stepped outside, I believed his cover story about getting tire advice. I was so convinced by the ruse that I kept asking about the tires as we went to bed that night — which still makes John laugh.
JOHN: I thought the tire diversion had worked. I was relieved my parents were excited too, so I waited impatiently for Saturday. I slipped the ring into our camera bag and packed it with hiking snacks and supplies.
SHERRY: I was excited for the hike even though it was cold. Joining us were John’s cousin Travis, his sister Carrie, and her boyfriend. The trail was challenging — almost six miles with plenty of rock scrambling. I like to joke that John made me work for my ring; there were spots where I had to be helped up by two people.
JOHN: I had told our hiking companions the plan: eat at the summit, then make ourselves scarce. At the top everyone vanished, which wasn’t quite the sequence I’d rehearsed. I had to catch up and whisper that we should eat first. Sherry might have noticed something odd, but she didn’t catch on.
SHERRY: At the top everyone chuckled quietly and I suspected I’d missed a joke. I was exhausted so I rested and ate, then looked forward to the downhill portion. It was chilly, and John insisted we take many photos before leaving. During our self-portrait attempt the camera “died,” so John went to the bag for “new batteries.”
JOHN: The camera dying was me hitting the off switch on purpose so I could reach into the camera bag for the ring. When I bent down, I pulled out the ring, spun back, dropped to one knee, opened the box, and asked, “Sherry, will you marry me?” Her jumping jacks stopped midair.
SHERRY: I was in complete shock. I froze, then ran to John and jumped into his lap while he was still kneeling.
JOHN: I reminded her she needed to say “Yes” to make it official. She did. We kissed, she cried, and we ignored passing hikers. It was perfect.
SHERRY: After a few minutes of being newly engaged, we emerged to find John’s sister and cousin waiting nearby. I shared the news between hugs and squeals, and we took pictures — the camera was, in fact, working. John’s cousin Travis even snapped a memorable shot while we kissed in the background.
JOHN: The walk down felt like the best hike of our lives. We were elated and oblivious to the cold and tiredness. Carrie announced to every passerby that we’d just gotten engaged, and strangers high-fived and congratulated us. Then two familiar hikers approached.
SHERRY: We were stunned to see John’s parents walking up the trail toward us. I couldn’t believe he’d coordinated such a surprise. Then I realized he was just as surprised — his parents had known the time and place and managed to show up on the backside of the mountain. They asked, “Any news?” before congratulating us. In all the excitement I forgot to show off my ring.
JOHN: We finished the hike accompanied by my beaming parents. They treated us to lunch at a small restaurant in Sperryville. It wasn’t fancy, but we loved it, and the memory is special — we still say, “Remember that lunch in Sperryville?” I was grateful my parents suggested it because my planning hadn’t extended much past the proposal itself.
SHERRY: After lunch I was still smiling from ear to ear. I called friends and family to share the news (my mom didn’t hear until she returned from her cruise). A few days later we emailed everyone we knew — including former coworkers who didn’t even know we were dating. Their surprised responses poured in almost immediately. This was the photo we included with our announcement:
That’s the story of our mountaintop engagement. We’d love to hear your stories too — where did you get engaged, how did it happen, and did you see it coming?