<p>The NBA star proposed to the model during a 2025 Valentine's Day trip.</p>

<p data-start="40" data-end="665">Model <a href="https://www.lofficielusa.com/fashion/hailey-baldwin-winnie-harlow-new-faces-tommy-hilfiger" target="_blank" rel="noopener">Winnie Harlow</a> and Milwaukee Bucks star Kyle Kuzma announced their engagement, marking a significant milestone in their nearly five-year relationship, Tuesday afternoon.</p>
<p data-start="40" data-end="665">The couple's journey began in 2019 when Kuzma reached out to Harlow <a href="https://www.lofficielusa.com/tags/instagram" target="_blank" rel="noopener">via Instagram</a>, 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 <a href="https://www.lofficielusa.com/fashion-week/christian-siriano-fall-winter-2025-review">walked during New York Fashion Week</a>) 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.</p>
<p data-start="667" data-end="1257">Kuzma proposed to Harlow during a romantic getaway to Turks and Caicos on February 13, 2025. He orchestrated a surprise <a href="https://www.lofficielusa.com/tags/valentinesday" target="_blank" rel="noopener">Valentine's Day trip</a>, decorating a private plane with roses, balloons, and champagne.&nbsp; He presented Harlow with an 8.5-carat oval-cut diamond ring that he designed himself.&nbsp;</p>
<p data-start="1259" data-end="1562">Reflecting on their engagement, <a href="https://www.lofficielusa.com/beauty/winnie-harlow-rupaul-mac-viva-glam-2019" target="_blank" rel="noopener">Harlow</a> posted photos to her Instagram of the engagement and her clear excitement.&nbsp; Keep scrolling for a look back at their full relationship timeline, which all started in Instagram DM's.&nbsp;</p>

winnie harlow kyle kuzma engagement

<p>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.&nbsp;</p>

<p>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.</p>

<h2>April 2020: Winnie Harlow Moves to Kuzma in LA</h2>

<p>After a month of virtual communication, the <a href="https://cayskin.com/">Cay Skin</a> founder made the spontaneous decision to move from Brooklyn to Los Angeles to be with Kuzma during the quarantine period.</p>

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

<h2>April 2021: Their First Anniversary&nbsp;</h2>

<p>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 🤍." The intimate clip gave fans a glimpse into their relationship, sparking warm reactions and well-wishes in the comments.</p>

<p>By December 2021, the couple was spotted hand-in-hand in New York City, indicating a reconciliation and renewed commitment to their relationship.</p>

<h2>May 2023: Winnie Harlow Cheers for Kyle Kuzma During the NBA Season</h2>

<p>Just as she did in the early days of their relationship, Harlow continued to support Kuzma&rsquo;s basketball career. She was spotted at his games, showing love for her boyfriend both on and off the court.</p>

<h2>August 2023: Winnie Harlow's "Kyle" Tattoo</h2>

winnie harlow kyle kuzma relationship

<p>Harlow took her commitment to the next level by getting a tattoo of Kuzma&rsquo;s name, a clear sign that their relationship remains strong and steady. She shared a photo on Instagram showcasing the delicate cursive ink behind her right ear, which spelled out "Kyle." The gesture not only demonstrated her deep affection for him but also silenced any lingering breakup rumors, proving that the couple is more solid than ever.</p>

winnie harlow and kyle kuzma engagement

<p data-start="2229" data-end="2456">Kuzma proposed to Harlow during a trip to Turks and Caicos. He crafted a heartfelt poem that culminated in the proposal, presenting her with an 8.5-carat diamond ring he designed himself. They were also surrounded by <span>florals from&nbsp;</span><span>Venus et Fleur</span><span>.&nbsp;</span></p>
<p data-start="2229" data-end="2456">From a missed message to a memorable engagement, we're excited to see the engagement turn into a beautiful marriage. Check back for updates.</p>

Winnie Harlow and Kyle Kuzma's Complete Relationship Timeline

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