How did Winnie Harlow meet Kyle Kuzma? Relationship timeline explored amid engagement

Winnie Harlow and Kyle Kuzma have been making waves across social media platforms with their engagement announcement.

The couple shared their news on Instagram on February 18, 2025, featuring love-up photos and clips from the engagement. The proposal took place during their romantic getaway to Turks and Caicos on Valentine’s weekend.

The 6-foot-9 Milwaukee Bucks player sealed the deal with a poem that concluded with, “Will you be my wife?” before opening an 8.5-carat oval-cut diamond ring, as per Mirror.

Talking to Vogue, Harlow admitted that a fleeting thought of a proposal crossed her wine.

“I still had no idea what this was. I was just like, 'This is so cute for Valentine's Day, oh my gosh!'” she said. "For a split second in my head I thought, 'This would be so cute if this was an engagement'."

She also added that she is not the type of person who wants to spoil a surprise.

The two met through a series of messages on Instagram. Initially, Kuzma slid into her DMs in 2019 but she never saw his message due to some glitch on Instagram, as told on the TheEllenShow in a 2021 interview. He tried again later in 2020 during quarantine and this time Harlow responded positively.

She recounted their conversation started with chatting about quarantine which led to FaceTime, “for 24 hours every single day for a month.” She then moved to Los Angeles to be closer to Kuzma. They made their relationship official on June 23, 2020, when they posted their first photo together, as per People magazine.

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The relationship timeline of Kyle Kuzma and Winnie Harlow explored

Kyle Kuzma and Winnie Harlow are currently “over the moon” as they took a big leap in their relationship. The couple has been dating each other since 2020 and this year they will be celebrating their fifth anniversary.

But before they began their whirlwind romance, the two were linked to notable celebrities. Kuzma was linked to Sofia Jamora (2015), Katya Henry (2018-2019), and Kendall Jenner (2019) until 2020 when he met Harlow. Whereas, Harlow had been linked to Lewis Hamilton (2017-2018), Wiz Khalifa (2018-2019), and Maluma (2019).

The couple has been quite private about their past relationships. Sharing her budding romance with People magazine, Harlow said that she met Kuzma “in sweats” when they began dating in 2020, which was a very down-to-earth way.

“Being in the pandemic, you had time to learn about somebody and get to know someone more than you did in regular life when we have work and so many things pulling us in different directions.”

She shared in an interview with Highsnobiety, as reported by People magazine.

They went Instagram official on June 23, 2020, when the two shared their first photos.

In February 2021, they celebrated their first Valentine’s Day. In her Instagram post, she wrote,

"Yes you drive me nuts but you put up with my crazy so I think that's a fair trade 😂😘 thank you for being a shoulder to cry on and a hand to hold. The best boyfriend a girl could ask for. Can't wait for more adventures with you. Love you issha mi widdle daddy bear 🥺🤣🥰." Kuzma too replied to her in an adorable post.

On April 23, 2021, the couple celebrated their first anniversary through an Instagram video that showed them sharing a kiss.

In August 2021 rumours of a breakup circulated the couple. However, the duo shut them down when they were spotted walking hand-in-hand in New York City. The exclusive photos were shared by TMZ.

In November 2022, the supermodel was spotted cheering her boyfriend during the Washington Wizards game against the Dallas Mavericks. She shared a series of pictures from the event on her Instagram and wrote -

"Someone tell 33 to give me a call ☎️❤️🤤🌸🌸”

During a June 2023 interview with Highsnobiety, Kuzma credited Harlow for leveling up his style game.

"One thing I have learned is how to completely finish a look correctly,” he told. "Winnie is very detailed with every single thing, [from] what the accessories look like [to] what attitude to rock with it. She’s really leveled up my energy."

Harlow added,

“He’ll try on his outfits on FaceTime with me and be like, ‘Do you think this hat or this hat? What about these shoes with this ’fit? Or should I put this jacket with this?’ ”

In May 2024, Winnie Harlow and Kyle Kuzma attended the amfAR Gala during the annual Cannes Film Festival, according to People magazine. The two have been going strong since their first date.

As of now, fans are excited about their engagement and are anticipating a marriage soon. However, neither Harlow nor Kuzma have announced a specific wedding date yet.