Did Whiz Khalifa and Winnie Harlow date? Canadian model’s dating history explored

Winnie Harlow and Kyle Kuzma are officially engaged, as the couple recently shared the massive update through their social media handles. Kuzma and Harlow had been in a relationship for almost five years before the NBA star decided to put a ring on it around Valentine's Day.

Before dating Milwaukee Bucks, Winnie Harlow was reportedly in a relationship with rapper Whiz Khalifa. The former couple was reportedly together for less than a year, between June 2018 and January 2019. After starting their relationship in the summer of 2018, Whiz and Winnie posted about one another quite frequently on Instagram. After going Instagram official, the ex-lovers also attended different events together.

However, in 2019, Whiz Khalifa and Winnie Harlow broke up and moved on to other relationships. Khalifa, who was married to Amber Rose between 2013 and 2016, soon started dating Aimee Aguilar. At the same time, the America’s Next Top Model contestant kept mum about her relationship status and ultimately started dating her current fiancé, Kyle Kuzma, in 2020 after the latter reportedly slid into her DMs.

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More about Winnie Harlow’s dating history after the supermodel gets engaged to Kyle Kuzma

Winnie Harlow shot to fame in 2014 with her participation in America’s Next Top Model. The fashion model soon got to work with many global brands on their advertisement campaigns while her personal life remained largely private. In September 2016, Winnie sparked dating rumors with British F1 racer Lewis Hamilton.

Harlow was spotted with Hamilton at the GQ Men of the Year Awards in 2016, which started speculations about their relationship. The rumored couple continued to be seen together at different occasions and events, but neither Winnie nor Lewis confirmed anything. Although it’s unclear when they broke up, both were last seen together in 2018.

In the summer of 2018, Winnie started dating Whiz Khalifa, which continued until early 2019. After the end of their relationship, Page Six reported the ongoing rumors that Winnie Harlow was dating Colombian singer Maluma after they had been seen together. The rumors never got any confirmation, and Harlow entered into a relationship with Kyle Kuzma.

Kyle texted Winnie on Instagram multiple times in 2019. The supermodel eventually responded to the texts of the NBA champion. The romance brewed in 2020 when the world was battling COVID-19, as the couple started dating in April. In June, they went Instagram official. She even recalled her first interaction on The Ellen Show in 2021,

“I got a DM, a year prior, from my boyfriend and I never seen it. I don't know when glitch in the system with Instagram is, but that never came up for me. A year later at the top of quarantine, he DMed me again. He posted a picture of me in, like, an outfit.”

She further told the guest host tWitch,

“He shot his shot, you know, slid in the DMs. So, that was cute and I was like, ‘Oh hey, like how's quarantine been?’ And yeah, we kind of just started talking from there and then he was like, after a month of being on Facetime for 24 hours, every single day for a month, he was like, 'You've got to come to LA,' and I've been in LA ever since.”

The couple got engaged in February 2025 after Kyle Kuzman proposed to Winnie Harlow with an 8.5-carat custom-made engagement ring. According to the couple’s Vogue interview, Kuzman took three months to design the ring, while he had planned the proposal for six months after having the idea in 2022.

Kyle Kuzman planned the proposal in the guise of a romantic getaway to the Turks and Caicos Islands, a location where they had spent a vacation in 2022, per Vogue.