One of our favorite parts of working on Over The Moon is finding out the proposal stories of the couples we feature—they’re sweet, romantic, and sometimes even funny, but above all they’re real. So in honor of Valentine’s Day, we took a look through our archives and pulled out some of our favorites—from Nicholas Rockwell jokingly proposing to Mary Beth Edwards with a blade of grass, to Andy Katz popping the question to Townsend Llyod at the couple’s favorite West Village spot, The Little Owl, and Liz Parker and Sarah Tallman’s not one, but two proposals!—these stories will have you believing in love.
“Minot loves to play backgammon and came up with an elaborate plan to propose by putting the engagement ring in the backgammon basket while we were playing,” says Julia. “But, much to his chagrin, the ring stayed hidden in the backgammon table at my parents’ home in the Hudson Valley for several days while we were visiting them for Thanksgiving. He kept offering to play, and I unknowingly would say I didn’t feel like it, ruining his creative plan. Eventually, he gave up and asked if I wanted to go on a walk in the woods with our dogs, Hudson and Gracie. About five minutes in, I realized he wasn’t next to me, and I turned around to find him down on one knee.”
During a particularly lazy Saturday morning, Nicholas Rockwell surprised his girlfriend Mary Elizabeth “Mary Beth” Edwards with breakfast in bed at their home in San Francisco. Along with scrambled eggs and extra crispy bacon, there was a small jewelry box on the tray. Inside lay a single blade of grass, which may have been a surprise for anyone else, but Mary Beth knew the meaning behind it. “I had always joked with my friends that I loved Nick so much that if he proposed with a blade of grass, I’d still say yes,” she explains. “Clearly this story had gotten back to him!” Nick later got down on one knee and pulled out the real ring, an oval cut sapphire flanked by two perfect, brilliant cut diamonds that had belonged to his grandmother.
“We were on a sports trip with our respective teams in the Netherlands, playing against the American School of the Hague,” remembers Jessamy. “It was four years prior, in The Hague, on a sports trip when we first kissed. The trips with the teams are a lot of fun—after the games are over, the coaches always go out for dinner and a few drinks. The ‘proposal trip’ started out like any other one, but when we got back to the hotel room, Charles got down on one knee!”
Andy was working in consulting and traveling Monday through Thursday most weeks. “He had mentioned that he would be home on a particular Monday as he had meetings locally and suggested we go to dinner at Little Owl, our favorite restaurant in the West Village,” says Townsend. “I thought it was a nice idea, especially as I was headed to San Francisco the following day for a business trip and wouldn’t see him until the weekend when we planned to head to Canada to visit my family.”
At the end of the meal, the waitress brought over a little black book with the check. It is tradition at Little Owl to sign the book at the end of your meal. “When I opened the book to sign it, there were two pages filled with photos of us and the words ‘Will you marry me?’ After I read it about four times, I finally looked up and saw Andy down on one knee with a ring,” says Townsend. “It took me some time to get over the shock factor, but I of course said yes and the excitement began to set in!”
“We were building our former house in downtown Charleston and had just finished the demo—so the whole inside was gutted down to the studs,” remembers Kate. “The project was big and at times quite stressful. The house didn’t feel like our own, but more of a money sucking job site. I was the contractor on the build, which was convenient but also very challenging. One evening while we were biking to dinner, Ben said he wanted to stop by the house to show me an exciting idea he had for the dining fireplace area. I had not been at the house that day as I’d been in desperate need of some time off from it all, and the last place I wanted to go was to that construction site. But, intrigued, I agreed and we cycled over. I could see a candle was lit through the holes in the wooden clapboard siding and instantly thought there was a homeless person sleeping in there. I barged through in front of Ben, and to my surprise, I found the whole inside filled with candles, our dining table from our apartment had been set with a gorgeous dinner, many bottles of Champagne, and Sam Cooke playing in the background. I turned around, and there was Ben down on one knee. I began jumping up and down, crying and laughing, and we danced the night away in our new home, which I saw in a whole new light from that night on.”
“Sarah’s birthday was coming up, and I knew I wanted to propose,” explains Liz. “But, I also knew I didn’t want to impose a lot of pomp and circumstance on her—so I settled on a letter, and presented it to her early one morning in Vail, where we were vacationing for a few days. I thought my letter was explicit and clear—I was even moved by my own words as I read over her shoulder—but it was not so for Sarah, who later told me she was touched by the letter and the sentiment, but did not totally understand that she was being proposed to. Luckily, the ring I presented afterwards helped clear that up, and she nodded ‘yes.’”
A few months later, Sarah took the opportunity to propose to Liz. “How she managed to surprise someone already engaged is a testament to her wits and my gullibility,” laughs Liz. “But, Sarah lured me up to her office on the edge of Central Park, alleging our car was parked nearby. I unwittingly followed her through the park, mostly excited for the pizza we planned to get later, when Sarah turned around and offered a ring. I said ‘yes,’ and we finished our walk at Whiskey Park, where twenty of our closest family and friends were waiting with a surprise Champagne toast.”
“We were in the same sign language class in college,” says Caroline. “Talking was strictly prohibited, so for months before we became friends outside of the classroom, we only signed to each other.” The two had been dating for about one and a half years when they ran into their sign language professor while walking to dinner in downtown Greenville, SC. “We stopped and said hello to his wife and he then proceeded to ask us to sign,” remembers Caroline. “He asked me questions like, ‘How long have you been dating Wyatt?’ and ‘Do you think you’ll get engaged soon?’ and then ‘How about getting engaged right now?’ Wyatt then took a knee.”
“My sister and brother-in-law were in town, and we were supposed to be meeting up with them for dinner,” remembers EJ. “Jake had just bought an apartment and movers had delivered everything earlier that day, so I went over before dinner to help out a little bit. I had had a dream the night before that he was going to propose to me that evening, so I psyched myself out a bit as I headed over. However when I arrived—expecting candles and flowers—I found the place a total mess, and Jake was downstairs yelling up at me for a belt. I quickly realized that I was crazy and in fact not psychic. Jake then had me stringing up lights in the garden outside, which bizarrely did not seem like a strange thing to prioritize at the time, but it was in fact because he had invited all our friends over to celebrate later. When I came inside he handed me a flat rectangular Tiffany box—that was definitely not ring sized. It had a keychain in it, and he said some sweet things about starting a new time in our lives together. I thought to myself: That’s adorable, but I’m not moving in so also sort of weird. Then he told me to look closer at the keychain. I realized there was a ring dangling off of it. He then got onto his knee and said, ‘Do you wanna get married?’ ” Not long after, EJ’s parents walked in along with her sister, brother-in-law, best friend, and Jake’s sister. “It was perfect,” she remembers.
“A few weeks before, he intentionally threw me off course by saying he thought we should live together for a least another year before getting engaged,” remembers Daisy. “He planned it all perfectly—it was incredible. I’m a total birthday brat, and he used that to his advantage. My birthday was on a Friday, and the next day, he told me he was going to make me brunch in bed. He brought me coffee and suggested I brush my teeth and get myself together a little before we ate. I was, admittedly, totally annoyed–who wants to get dressed for breakfast in bed? Then, when I came out of the bedroom at his calling, there were rose petals leading to the living room, a bottle of amazing champagne on the table, and he got on one knee. I’m not sure I ever even said ‘yes,’ so much as shrieked a lot. My family is located all around the country—my parents are based in San Francisco, my dad was, at the time, on a business trip in China, my three sisters are in San Francisco, Boston, and DC—and he secretly coordinated with all of them to fly in that day. Later that night, he planned a big dinner with his family and, to my complete surprise, mine as well, in the downstairs room at the Marrow. We then walked to get drinks at Analogue, a bar in the Village, and about thirty to forty of our friends were there to surprise me, again. There was also a giant Momofuku Milk Bar birthday cake, my favorite. It was the best day!”
After a long work week, Page, his brother, William, and Carrie were flying to the Crozer’s hometown, Thomasville, GA, for Easter weekend with both of the couple’s families. “We’d had many gatherings before with our families, so it didn’t occur to me that this could be THE weekend. After working most of the 45-minute flight, I had just closed my laptop when the pilot announced we had to circle back to check out a fire in the area,” explains Carrie. “Having never heard the pilot make announcements on the intercom and curious as to why we had to see this fire, I found it a bit odd, but was too distracted with work to think too much of it. Then moments later, the pilot told me to look out the window and I saw letters on the ground below. There was a message to me: CARRIE, WILL YOU MARRY ME? spray painted on one of the pond damns on their hunting plantation. As that registered, I immediately turned to Page who by then had grabbed my hands and was kneeling down. He told me how happy I’d made him and asked me to marry him. Everything stopped in that moment, and it was just incredible. William had been there to take pictures and capture our reactions to it all.”
“We were attending the Rockville Regatta with about twenty close friends,” says Jessica. “At the end of the first race day, we went to ‘The Dance’ at the Sea Island Yacht Club. Richard asked me if I wanted to cool off outside, and we walked down to the water. All of a sudden, he was down on one knee. I was shocked. I’ll always remember that he asked: ‘Will you be my wife?’ Not: Will you marry me.’ It sounded so thoughtful, like he fully realized the commitment he was making. We returned to our friends, and everyone jumped in the pool, where we danced—yes, in the pool—until about 3:00 a.m.”