Winnie Harlow and Kyle Kuzma's Complete Relationship Timeline

Model Winnie Harlow and Milwaukee Bucks star Kyle Kuzma announced their engagement, marking a significant milestone in their nearly five-year relationship, Tuesday afternoon.

The couple's journey began in 2019 when Kuzma reached out to Harlow via Instagram, subtly sliding in her DM's. Although the Canadian model didn't see his initial message, Kuzma's persistence paid off, and they eventually connected in early 2020. Their bond deepened during the COVID-19 pandemic, with Harlow (who just walked during New York Fashion Week) relocating to Los Angeles in April 2020 to be with the NBA star. They made their relationship public in June 2020 and have been inseparable since, though they had a brief split in 2021.

Kuzma proposed to Harlow during a romantic getaway to Turks and Caicos on February 13, 2025. He orchestrated a surprise Valentine's Day trip, decorating a private plane with roses, balloons, and champagne.  He presented Harlow with an 8.5-carat oval-cut diamond ring that he designed himself. 

Reflecting on their engagement, Harlow posted photos to her Instagram of the engagement and her clear excitement.  Keep scrolling for a look back at their full relationship timeline, which all started in Instagram DM's. 

2019: The Initial Outreach

Kyle Kuzma, intrigued by Winnie Harlow, sent her a direct message on Instagram. Unfortunately, due to a glitch, Harlow never saw this initial message, but what's meant for one will come to them, and things eventually worked out just fine. 

March 2020: Reconnection

Undeterred, Kuzma reached out again in March 2020. This time, Harlow received his message, which eventually led them to daily FaceTime conversations that deepened their connection.

April 2020: Winnie Harlow Moves to Kuzma in LA

After a month of virtual communication, the Cay Skin founder made the spontaneous decision to move from Brooklyn to Los Angeles to be with Kuzma during the quarantine period.

June 2020: Instagram Official

The couple publicly acknowledged their relationship by sharing photos together on Instagram, signaling their official relationship status to fans and followers.

April 2021: Their First Anniversary 

Harlow marked her and Kuzma's first anniversary with a heartfelt Instagram post. Sharing a video of the couple sharing a kiss at a restaurant, she captioned the moment, "Happy 1 year anniversary @kuz