Winnie Harlow Reveals the Most Thoughtful Surprise Kyle Kuzma Planned Before Proposing

The supermodel and entrepreneur and NBA player got engaged around Valentine’s Day in Turks and Caicos.

Kyle Kuzma and Winnie Harlow / Mark Thompson/Getty Images

Winnie Harlow and Kyle Kuzma’s engagement was nothing short of a fairytale, complete with a private jet, a heartfelt love letter and a stunning Turks and Caicos backdrop. But as the supermodel recently revealed on Call Her Daddy, the NBA star’s attention to detail was immaculate.

The Milwaukee Bucks player, who was traded from the Washington Wizards last month, popped the question on Feb. 13 during a romantic getaway to Turks and Caicos, a place that held sentimental value for the couple. During their first visit to the island in 2022, Harlow told Kuzma that a night swim under the stars had been one of the best moments of her life. From that moment, he knew it was the most serene and ideal setting to pop the question.

The surprise began before they even landed. Kuzma led Harlow, 30, onto a private jet decorated with balloons, chocolates and champagne, making her believe it was simply an extravagant Valentine’s Day gesture. But once he handed her a love letter and began reading it aloud, the Cay Skin founder started to sense something special was happening.

“At the end of the poem, the way he wrote it, it was like as if he was going to say, ‘Will you be my Valentine?’” Harlow told host Alex Cooper on the podcast. “And it was, ‘Will you be my wife?’”

Overcome with emotion, she immediately burst into tears before Kuzma even pulled out the ring. The dazzling 8.5-carat oval-cut engagement ring, which the 29-year-old athlete spent three months designing himself, featured two elegant baguette stones on the side—perfectly embodying the timeless and sophisticated aesthetic he envisioned for Harlow.

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But perhaps the most thoughtful part of Kuzma’s plan happened days before the trip—without Harlow realizing it. The SI Swimsuit legend, who posed for the magazine in the Bahamas in 2019 and returned to the fold for the milestone 60th anniversary issue last year, explained that her longtime nail technician, who is based in Los Angeles, had reached out and offered to come to Washington, D.C., where she had been living with Kuzma, to do her nails and lashes.

“I was like, ‘Oh, babe, guess what? My nail tech is coming out here, such a coincidence!’” the Canada native shared. It wasn’t until later that she learned the Michigan native had secretly arranged the visit, ensuring her nails would be picture-perfect for the moment of a lifetime.

The surprises didn’t stop there. After saying yes, Harlow landed in Turks and Caicos expecting a private getaway—only to be greeted by their closest family and friends, whom Kuzma had secretly flown in for the occasion.

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Harlow and Kuzma, who have been dating since 2020, met during the pandemic after she missed a few of his DMs—until she finally saw one when they both became Puma ambassadors.