Supermodel and entrepreneur Winnie Harlow makes an appearance on The Jennifer Hudson Show, airing Monday, May 11, and opens up about her unforgettable surprise proposal. From a romantic getaway in Turks and Caicos to a heartfelt letter from fiancé Kyle Kuzma, what Winnie believed was simply a beautiful vacation quickly became a life-changing moment surrounded by love and family. She also shares what makes their relationship work so well, from their playful chemistry to the way they embrace and support each other’s bold sense of style.

Winnie also gets candid about what representation truly means to her and why one powerful moment recently brought her to tears. She reflects on the mindset that’s helped her push through rejection, stay grounded in her purpose, and never allow “no” to define her future.

Plus, Winnie discusses her children’s book, “Simply Winnie,” and her mission to make representation feel natural not “different” for the next generation. From sharing her entrepreneurial journey at Harvard Business School to building her inclusive skincare brand, Winnie opens up about creating spaces where everyone feels seen. She also reveals the unforgettable story of how a chance encounter turned into a real-life friendship with Shakira.

So much has changed since the last time you were here including your engagement to NBA star Kyle Kuzma! Congratulations!
When asked about the dreamy proposal, Savannah revealed she had absolutely no idea it was coming. The couple had planned a romantic Valentine’s Day getaway to Turks and Caicos, and Savannah thought Kyle was simply going all out for the holiday. But once they boarded the plane, he handed her a heartfelt note and asked her to sit while he read it aloud. The final words? “Will you be my wife?”

Savannah said she immediately burst into tears, overwhelmed with emotion. What made the moment even more special was Kyle secretly arranging for all of their family and close friends to be there waiting when they landed in Turks and Caicos. “He thought of everything,” she shared.
The couple also opened up about their fun relationship dynamic from Kyle encouraging Savannah to improve her basketball skills (including attempting a dunk! to the two bonding over tap dancing classes together. Savannah joked that Kyle got a little too into it and nearly hit the ceiling during one energetic freestyle move.

And of course, fashion came up too! The stylish pair admitted they both have strong personal style, but still love asking each other for opinions when putting looks together. Whether it’s choosing the perfect shoe or deciding on a hat, they clearly enjoy inspiring each other both individually and as a couple.
Honestly, they look so happy together and we love seeing it!