Why My Fiancé and I Designed Our Engagement Rings Together
From the beginning of my relationship with Liv, taking the next step was always a collaboration. When we decided to make it official, we sat next to each other at an empty Upper East Side bar over cocktails as we deleted our dating apps one by one. A little over a year into dating, we sent each other hundreds of StreetEasy links and finally settled on the perfect Williamsburg apartment to move into with each other (and Liv’s cat, Ella). We’ve worked together to divide up menus to share the perfect meal, plan our social schedules and holidays, and choose which next show to binge.
Throughout those years, we also always talked about what our future would look like, from marriage to how many kids and pets we wanted. After throwing a very successful Halloween party—we pulled out all the stops for food, decorations, and our Taylor Swift and Travis Kelce couples costumes—we felt as if we had shifted into a new “era,” if you will. All our friends from both sides of our lives got along, and we had found home not only in our space, but in each other. We knew we would want to propose to each other within the next year.
When we began talking about engagement, it made sense that it would once again be a collaboration. Since I have covered weddings for publications including Vogue, Brides, and The Knot over the years, I had a bit more insight into the ring shopping process than your average person—but I still wasn’t sure what stone was right for my own hand. Liv had accompanied friends when getting inspiration for their own engagement rings, but hadn’t yet learned the 4Cs, or really thought about what she would want herself. We decided that before diving into designing each other’s rings, we should get to know what we actually would like to see on our hands for the rest of our lives.
On an emotional day after Liv lost her grandfather mid-November, we began talking more about our families and futures together. Spur of the moment, we decided to stop into a jewelry store and try on a few styles. While we were far from choosing our real rings on that day, there was something special about having that moment together. Seeing a diamond on Liv’s finger and imagining a near future where I would call her my wife brought a flutter to my chest and a well of tears to my eyes. (Even writing this now brought about the exact same reaction.)
By the time the new year rolled around, we dove deeper into our search. I had mentioned to a wedding industry PR friend that we were starting to look for rings, and she suggested we meet with Hannah Florman Fine Jewelry. Based in a beautiful brownstone on Boston’s Newbury Street, Hannah and her small team create custom engagement rings and fine jewelry with an emphasis on individual collaboration with her clients.
When Hannah welcomed us into her stunning space, The Brownstone, she began with a rundown of diamond grades and settings. Hannah explained that you have to find a balance between the various “4Cs” to get the best stone for your budget. We had quite a bit of fun playing around with stones and bands. Hannah also asked us to look in a floor-length mirror to get the full feel of what a ring could look like as a day-to-day addition to our ensembles. I had suggested an emerald cut fit Liv’s vibe perfectly, but it took her seeing it in that full mirror to realize it was the right shape for her. An excited grin and spark came to her eyes. She turned to me and said, “I can’t believe I’m going to be your wife.”
Getting a feel for different ring settings with Liv and designer Hannah Florman.
Photo: Genevieve De Manio
After leaving Hannah’s, we needed to get serious about our budget. Like many couples, our incomes are quite different—but unlike many couples, we were both planning to purchase engagement rings. While these were some of the tougher conversations for us to have, ultimately it brought us to a point where we could talk transparently about our finances before we moved into the wedding planning process and marriage.
We also had a new timeline at hand. I had an opportunity to take a press visit to the Four Seasons Bora Bora at the end of June and could take Liv along with me. Initially, we imagined doing a proposal and counter-proposal, where we would each surprise each other with our rings at a different time. But, the opportunity to propose in the paradise of Bora Bora was too exciting to pass up. We asked Hannah about her production turnaround, and booked a visit with her a little over a month ahead of our trip.
For the second consultation with Hannah’s team, she sourced specific diamonds for us that met our budgets and preferences. While renting a car for the drive from Brooklyn seemed like a great idea at the time of booking, a torrential thunderstorm along the majority of our four-hour trek (and a lack of umbrellas) added an unexpected touch of chaos to the day. Luckily, the ever-accommodating Hannah procured us a blow dryer so we wouldn’t be dripping as we selected our stones. Once dry and with prosecco in hand, we sat down to see the natural diamonds Hannah had sourced for each of us.
The moment we decided this diamond was the one.
Photo: Genevieve De Manio
Celebrating at The Brownstone.
Photo: Genevieve De Manio
Of the two marquises for my ring, one was more long and slender with higher clarity, while another was a slightly wider stone with higher color. The second diamond made an impact that put a goofy smile on my face. Liv and I looked at each other and knew that was my ring. Next, we looked at emerald-cut diamonds for Liv’s ring. Since her setting would be a simple platinum band without any additional stones, she wanted the diamond to stand out in size and clarity. All the choices were beautiful, but the winner was clearly a 2.04-carat, VS2 diamond that made Liv’s eyes widen.
While Liv and I were keeping our settings relatively simple, there were a few details to work out. While some prefer high, intricate settings, we both agreed that we would want our diamonds to sit lower. We are everyday jewelry people and wanted our rings to fold seamlessly into our lives. Hannah recommended we choose flush settings, which would still allow for a wedding band to easily stack with our engagement rings. We left the meeting on a high, immediately Facetimed both our parents together to tell them the good news, and celebrated with dinner in Boston’s Little Italy.
A week later, Hannah sent us CAD renderings of what our rings would look like for final approval. I left our apartment building to get out of earshot of Liv to hop on a quick call with Hannah. While I do think designing our rings together was essential, I still wanted an element of surprise. I asked Hannah if it would be possible to add a small engraving inside the band, and she walked me through the process of how I could easily send her my message in my own handwriting via email. I confirmed the final design and Florman got to work.
Finally, with the rings in production, it was time to plan the double proposal. While we both would propose at the same time, I asked Liv if I could make part of it a surprise. She gave me the go-ahead and I got in touch with the events team at the Four Seasons Bora Bora. Off the property’s main beach was a tiny island called a motu that they set up for private dinners. We would take some photos around the property with a photographer, get canoed to the motu, and have the proposal and a three-course dinner take place there at sunset. All I told Liv was on Saturday night of our trip, she would need to bring my ring along with her and be ready for some photos. (Since we both knew when the proposal was happening, it also allowed us to have some fun with the fashion for our big moment. I reached out to Over the Moon, run by Vogue’s contributing weddings editor Alexandra Macon, and asked if they could help style us for the engagement—style director Grace Givens helped lead me to a Fanm Mon dress with floral embroidery for a classic look, while Liv chose a modern Galvan midi dress with a cool wavy cutout.)
The rings arrived via insured mail the Friday before our trip, and although I’ve always been the sort of person to take a peek at the hidden presents my mom was wrapping for the holidays, as we kept our ring boxes out in the open for days, I held myself back from looking at my own. I wanted to feel the excitement in the moment. So with our newly insured rings in our personal item baggage, we took the long trek to Bora Bora—and the destination was worth the multiple flights. After a few nights of settling into our overwater bungalow, the proposal day arrived as our home in New York was in the midst of Pride celebrations. That afternoon, Liv and I grabbed to-go piña coladas from the beach bar to enjoy while getting ready. However, I could see the motu getting decorated for the proposal in the distance. Nervously, I kept pointing to fish in the water and other parts of the hotel’s scenery to distract her gaze from the direction of the surprise.
Photo: Sasha Popovic
As we put on our dresses and did our makeup for the proposal, Liv began to tear up with excitement for the surprise ahead. I held it together until I got a phone call with some news. Due to high winds, we wouldn’t be able to host dinner on the motu. While I wasn’t nervous before, a wave of anxiety washed over me. However, everything was going to work out. The proposal would still be able to happen on the island and the events team sprung into action to decorate a small chapel overlooking a lagoon for our dinner.
A knock at our door arrived and a golf cart was there to take us to meet with our photographer, Sasha Popovic. He led us around the property for an engagement shoot sans rings. (Liv and I laughed our way through some of the awkwardness of taking so many pictures, but we joked it was a crash course for our future wedding portraits.) Once we arrived at the beach, a canoe arrived from around the corner to take us to the motu. Liv admitted that she had a feeling about the surprise after all my attempts to distract her earlier—but that it still felt magical to arrive on the island, which was decorated with palm fronds and designs in the sand.
Photo: Sasha Popovic
After taking a few photos, we looked at each other with eyes that said: “It’s go time.” We grabbed the pink ring boxes from our bags and headed to the center of the tropical display. Liv and I never fully decided who would go first, but as the person who organized the island surprise, I went for it. Of course, the moment I started talking about how I love her and was excited about our life together, tears started taking over. It was a bit of a blur as I got down on one knee and asked Liv to marry me.
Photo: Sasha Popovic
We kissed, and then Liv began her proposal speech. When we first started dating, we would often talk about what love really means, and Liv said that I taught her what a real, deep love actually feels like. I stopped her in the moment and told her to look inside the ring I just gave her. The engraving I had designed inside her ring said, “Thank you for teaching me what love is…” She got down on one knee and showed me my ring. It was even more beautiful than I had imagined. Liv also surprised me and had the words “my love” engraved in her handwriting inside.
Photo: Sasha Popovic
We were giddy with smiles as we returned to shore and headed to our celebratory dinner. When we arrived, we found the pathway to the chapel lined with bright flower petals and palm leaves. Inside, a beautiful table was set up with flowers, colorful linens, and personalized menus. After a bottle of Champagne was opened, we toasted to our futures and spent the rest of the night calling friends and family, eating our incredible meal, and staring at the rings.
Photo: Sasha Popovic
Reflecting on the process, Liv and I couldn’t imagine ourselves designing each other’s rings alone. Not only did we make sure that we selected stones and settings we loved, but it felt romantic to work on creating such special symbols of our love together and infuse surprises along the way. I love that our double proposal allowed us to enter our next stage of life as a partnership—and hope that continues in the many years to come.
Photo: Sasha Popovic
