Drake's dating timeline explored after reported ex Serena Williams goes viral for crip walking at Kendrick Lamar's Super Bowl halftime show

Kendrick Lamar's Super Bowl LIX performance on Sunday, February 9, 2024, featured an apparent dig at Drake as Lamar brought one of Drake's exes, Serena Williams, onstage. In a surprise appearance, the tennis icon came out onstage to dance along to Not Like Us, one of Lamar's diss tracks aimed at Drake.

Williams joined the backup dancer while performing the 'Crip Walk.' Her unexpected cameo during Kendrick Lamar's 13-minute set at the Caesars Superdome made headlines, leading fans to revisit the long-standing rumor that she once dated Drake.

Although they never explicitly confirmed it, multiple outlets have reported that they dated sometime between 2011 and 2015. The Family Matters rapper referenced the tennis icon in some of his songs over the years.

Kendrick Lamar's Super Bowl Halftime show also featured SZA, who also previously dated the Canadian rapper. That said, Serena Williams and SZA weren't the only high-profile personalities Drake has dated.

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Drake's star-studded dating history explored

Among the high-profile names who were once romantically linked with Drake include SZA, Rihanna, Serena Williams, Tyra Banks, and Jennifer Lopez.

SZA

SZA and the Canadian rapper dated in 2009, but it wasn't known then until he name-dropped her in the 2020 track Mr. Right Now, claiming that they were once a couple.

While he said in the song that he "used to date SZA back in '08," the Kill Bill singer debunked the timeline in an October 2020 tweet, saying:

"So it was actually 2009 lol ... in this case a year of poetic rap license mattered lol."

SZA also opened up about their past romance in interviews. She said that she and the Canadian rapper have "always been cool" in her December 2022 interview with Audacy.

She also told Rolling Stone in October 2023 that her past with Drake was "youth vibes" and "childish" as opposed to "hot and heavy."

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Rihanna

Rihanna also dated the rapper on and off sometime between 2009 to 2016, although neither confirmed the romance. He famously professed his love for the Umbrella singer during the 2016 MTV Video Music Awards, and they were frequently seen together on dates, per Billboard.

Page Six also reported a night out where Rihanna was "making out with him all night" in New York in 2009.

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Serena Williams

As for Serena Williams, the rapper references her in songs like Worst Behavior in 2013 and also credited her for being an inspiration for him to finish Back to Back in 2015, per Entertainment News.

He also name-dropped her on the song Too Good in 2016, per Newsweek. Drake also told Rap Radar in 2019, "I was with Serena at the time."

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Tyra Banks

Another name romantically linked to the Canadian rapper was Tyra Banks. Theirs, however, was only a single date. The rapper said on The Ellen DeGeneres Show in 2013 that he went out with Banks to Disneyland in 2012, saying:

"I went on a date with her one time, yeah. We went to Disneyland in disguise, actually, which was fun."

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Jennifer Lopez

The God's Plan rapper and Jennifer Lopez also dated briefly sometime in 2017, per Entertainment News. They first sparked dating rumors in December 2016 after he attended her Las Vegas residency and reportedly gifted her a $100,000 diamond necklace.

People also reported that they dated around January 2017, and the rapper even met Lopez's children, but the romance fizzled out by February of that same year.

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Drake also dated Sophie Brussaux, the mother of her son, Adonis, briefly in 2017 after his split with Lopez, per People, and he last dated Johanna Leia in 2021.