This Fairy-Tale Wedding at the Bride’s Family Home on Martha’s Vineyard Was Filled With Blush Pink Hues and Quatrefoil Accents

Chelsea Grain and Amile Jefferson were first introduced in 2013 during the second semester of their freshman year at Duke University through a series of orchestrated meet-cutes. “We had a close mutual friend named Mercedes—who is now my best friend and was my maid of honor—and she spent months trying to set us up,” Chelsea, who is now a graduate student at Harvard Business School and the former manager of original film content strategy and analysis at Netflix, remembers. “She would invite me to breakfast, and boom, Amile would be there too. She’d invite me to a party, and he’d be the first person I saw when I walked into the building. After a while, it became funny. I could expect to run into him 80% of the time whenever she invited me anywhere.” At some point during the semester, Chelsea and Amile started to really hit it off and began dating.

Eight years later, on August 16, 2021, Amile, who is a former NBA basketball player for the Minnesota Timberwolves and the Orlando Magic and the current Boston Celtics assistant coach, proposed to Chelsea in her family’s backyard on Martha’s Vineyard while her parents, brother, and grandmother looked on through the back window. “He did it under the guise of a breakfast meeting we had at the house for his job,” Chelsea remembers. “I was rushing to get dressed and finally made it downstairs and noticed a pillow on the lawn. Fully thinking that the wind had taken it, I ran out to move it back to the porch. Amile took it out of my hands and chucked it off into the hydrangea bushes. In the heat of the moment, while frantically hurrying, I started to ask him why on earth he was slowing me down when we had this important meeting, but then I looked at his face and noticed tears in his eyes. He got down on one knee in white pants and pillowless because he had thrown it off to the side.” Overwhelmed with excitement, to this day, neither of them have any idea what was said—other than that Chelsea said yes.

What Chelsea hadn’t known is that a few weeks prior, Amile had gone ring shopping in New York with her mother. Amile and his future mother-in-law sat down with Lowell, the owner of Kwiat—Chelsea’s favorite jeweler—and he got a full lesson on the 5 Cs. “After the lesson, Lowell laid out diamonds, and my mom told Amile to take his time and pick one,” Chelsea explains. “She stepped out to give him the privacy to make this decision on his own, and it was a beautiful choice.”

A decision regarding where to have the wedding was just as seamless. Chelsea’s family has been going to Martha’s Vineyard since the 1940s, and the island has always held a very special place in her heart as a result. “Over a decade before Brown v. Board of Education and desegregation in the United States, Martha’s Vineyard was a diverse island with Indigenous, Black American, and many immigrant communities,” Chelsea says. “For Black Americans in particular, it has historically been regarded as one of the few safe havens to rest, vacation, and socialize with one another without experiencing the same level of discrimination they faced daily on the mainland. My grandparents retired and were buried there, my dad grew up and went to high school there, I met my closest friends, learned to ride my bike, and drive a car there. It was the only place where I got to spend time with other Black kids, see girls on the beach who looked like me, donning the same stretch marks forming around their hips and hair growing by the second with the humidity. It was the first place I ever felt that I belonged—it was home. I moved every few years my entire life, but my constant was the island. Every summer since I was born, I knew I’d get to reunite with my friends and family on Martha’s Vineyard.”