This Vogue Weddings Writer Tried on 100 Dresses for Her Brooklyn Wedding

When Shelby Wax and Olivia Rosen matched on the Lox Club dating app in December 2021, Olivia sent Shelby a simple message: “Hi.” Shelby, a contributing writer at Vogue who covers weddings, needed a little more effort than that, so she “fully ghosted” the conversation.

But as the fates would have it, that first “hi” wouldn’t be their last. The next month, while they were both sick at home with COVID, they matched again, this time on Hinge. Shelby recognized Olivia (who goes by Liv and works as an enterprise account executive at Oracle), remembering a photo of her with a Ruth Bader Ginsburg photo in the frame. Shelby reached out and they started chatting. They decided to meet up as soon as they both tested negative.

On January 17, 2022, they met at Ruffian, a wine bar in the East Village, for their first date. “I arrived and automatically was taken aback at how beautiful Liv was and what a cool aura she had about her,” Shelby says. It took a moment for Liv to open up, but soon they both realized how much they had in common—from their dedication to their families, to their love of travel, to their soft spots for a good karaoke night.

After sharing a bottle of wine and small plates, they went to Lovers of Today, a speakeasy-style bar around the corner, for a nightcap. The conversation flowed easily. At one point, Liv asked Shelby what her “type” was. Shelby replied, “You,” and leaned in for their first kiss.

Liv describes a special trip to Hudson—where they went for their third date—as a turning point in the relationship. She felt even more sure just a year later. “At a dinner with all of Shelby’s friends, I very prematurely announced to the table, ‘I’m going to marry her.’ And here we are.”

Back then, Shelby was a senior editor at Brides, so the subject of marriage came up relatively early on. “Around our two-year anniversary mark, we were already living together, we’d traveled together, we’d been each other’s wedding date, and had become close with each other’s friends and families. We thought it was about time to get serious about rings,” Shelby says.

They designed their engagement rings together “so it would be a shared, collaborative experience and we could each get exactly what we wanted,” Shelby says. Boston-based designer Hannah Florman worked on both, helping the couple to find the stones and styles that best suited them. “I went with a marquise on a thin, gold pavé band and Liv chose an emerald-cut solitaire on a solid platinum band. For a little personalized surprise at the engagement, Liv and I both had different phrases inscribed inside for each other in our handwriting,” Shelby shares.

At first, they planned to propose to each other at different times. But when Shelby was invited on a press trip to the Four Seasons Bora Bora, they both felt it would be the perfect place for a double proposal—with a few surprise elements.