If you’ve been keeping up with celebrity news lately, you’ve probably heard about Winnie Harlow’s dreamy engagement to NBA star Kyle Kuzma. The Canadian supermodel, who first caught our attention on America’s Next Top Model and went on to become a Victoria’s Secret angel, has been absolutely glowing since saying “yes” to her basketball beau.
Born Chantelle Whitney Brown-Young, Harlow has become not just a fashion icon but an inspiration for many, breaking barriers in the modeling industry and becoming a powerful voice for representation.
Her journey from ANTM contestant to walking runways for Fendi and Marc Jacobs, appearing in campaigns for MAC and Swarovski, and gracing the covers of major magazines has been nothing short of remarkable.
But while her professional life has been an open book, her romantic journey has been equally fascinating. From a Formula 1 champion to a chart-topping rapper, let’s take a stroll down memory lane and check out the men who captured the heart of this stunning model before she found her forever love.
Lewis Hamilton (2016-2017)
Remember when the modeling and racing worlds collided? That’s exactly what happened when Winnie Harlow was first linked to British Formula 1 racing champion Lewis Hamilton. The pair first got tongues wagging in late 2016 when they showed up together at the GQ Men of the Year Awards – talk about a power couple entrance!
Throughout 2017, these two were practically jet-setting royalty, popping up at glamorous events from the sun-soaked streets of Cannes to the prestigious racing circuits of Monaco.
You’d spot them living it up in Monte Carlo one day and soaking in the Greek sunshine the next. But here’s the kicker – despite all those picture-perfect moments, both Hamilton and Harlow kept insisting they were “just friends.”
Even when Hamilton appeared on The Ellen DeGeneres Show in October 2016, he played it cool, telling Ellen he wasn’t dating anyone. The last time we saw these “friends” together was at the 2018 CFDA Fashion Awards, where they proved that sometimes, you can keep things friendly with your ex – if that’s what they really were!
Wiz Khalifa (2018-2019)
Just when we thought Winnie’s dating life couldn’t get more interesting, enter Wiz Khalifa! This romance kicked off in the summer of 2018, and unlike her previous relationship, there was no hiding this one. These two were basically the king and queen of Instagram PDA, dropping hints about their relationship through flirty posts that had fans double-tapping like crazy.
By October 2018, they made things Instagram official after being spotted courtside at a Lakers game (little did we know this would foreshadow Winnie’s future relationship!). Want to talk about commitment? Wiz even rocked a gold nameplate necklace with “Winnie” spelled out – now that’s what we call wearing your heart on your neck!
The relationship got the seal of approval from an unexpected source – Wiz’s ex-wife, Amber Rose, who showed her support by leaving sweet comments on their photos together. Winnie was living her best life, with Wiz cheering her on as she strutted down the Victoria’s Secret runway. But as these things sometimes go, their romance fizzled out in 2019.
Things got a bit weird when fans started tagging Winnie in posts showing Wiz with another woman. But she responded with total class, writing,
Lol leave me out of it ❤️ she’s pretty tho!
Now, that’s how you handle a breakup in the public eye!
Maluma (2019)
Speaking of sparks flying, 2019 was quite an interesting year for Winnie’s love life! The supermodel had the internet buzzing when she was linked to Colombian heartthrob Maluma. These two definitely knew how to keep fans guessing – between their flirty social media exchanges and public outings; everyone was trying to figure out if love was in the air.
Picture this: Harlow and Maluma were spotted having a great time at a Latin restaurant in Long Island City with friends, and later, she was seen dancing with the “Hawái” singer at a party.
But wait, there’s more! The social media sleuths went into overdrive when Winnie dropped heart-eye emojis on Maluma’s shirtless pics and fired emojis on his Instagram milestone celebration. Talk about keeping us on our toes! While they never officially confirmed any romance, their chemistry definitely had everyone talking.
Finding her forever love
Well, as they say, everything happens for a reason, and Winnie’s past relationships paved the way for her true love story with Kyle Kuzma. Here’s a modern romance for you: Kuzma actually tried to shoot his shot in her Instagram DMs back in 2019, but thanks to what Winnie calls a “glitch in the system,” she never saw it. Talk about divine timing!
When Kuzma tried again a year later, the stars finally aligned. After a month of marathon FaceTime sessions (we’re talking 24 hours a day, folks!), Winnie made the “very spontaneous” decision to relocate to Los Angeles.
Fast forward to February 2025, and Kuzma pulled off a romantic proposal that would make any rom-com proud, complete with a custom-designed ring he spent three years perfecting.
Looking back at Winnie’s dating history, it’s clear she’s always kept it real while keeping things classy. Whether dealing with public speculation or handling breakups in the spotlight, she’s shown us how to navigate romance with grace. And hey, sometimes you have to kiss a few frogs (or, in her case, date a racing champion and a rapper) before finding your prince – an NBA star!
This post belongs to FandomWire and first appeared on FandomWire
