Did Serena Williams Really Date Drake? What To Know About Their Tumultuous Relationship

So, did Serena Williams finally admit that she dated Drake by appearing during Kendrick Lamar’s 2025 Super Bowl halftime performance?

If you missed the show, Lamar obviously sang his Grammy-winning Drake diss track “Not Like Us,” and had Williams come onto the stage with him to dance. Now, that is some petty goodness that the internet can’t get enough of. However, this is the first time many fans even figured out that Williams and Drake seemingly dated.

Did Serena Williams & Drake Date?

Yes, Williams reportedly dated Drake before Williams married her now-husband, Alexis Ohanian. Williams and Drake reportedly dated on and off between 2011 and 2015.

“Serena briefly dated Drake around 2011 and even though it didn’t end that well, they have remained friends since,” an insider told Page Six in August 2024. Their romance may have only been a few months-long fling but the two were in each other’s lives for several years.

Let’s take a look back on their alleged fling.

Drake & Williams Were First Linked in 2011

The first signs we saw of anything brewing between the Canadian rapper and the tennis champion was in 2011 when Drake tweeted her on Aug. 4, writing: “@SerenaWilliams I cannot wait to put it on you and make you sweat……. during our match this weekend.”

Days later, the rapper was seen attending one of Williams’ matches in Canada.

Drake Rapped About Williams in His 2013 Track ‘Worst Behavior’

The first of multiple lyrical shoutouts to Williams came in Drake’s 2013 hit, “Worst Behavior,” in which he raps, “I’m with my whole set, tennis matches at the crib, I swear I could beat Serena when she playin’ with her left.”

Drake & Williams Were Linked Throughout 2015

Their allegedly on-off romance seemed to heat up significantly in 2015 when Drake was spotted showing support to Williams at several events.

In August, TMZ obtained photos of the pair allegedly kissing during an intimate dinner. The following month, the rapper attended the US Open, sitting courtside during Williams’ devastating semifinals loss, just two victories shy of earning a calendar-year Grand Slam. Williams was seen leaving the game in Drake’s car.

Interestingly, Williams’ now-husband Alexis Ohanian also supported her at the US Open that same month, seemingly in the early stages of their relationship.

Also in September, he attended a fashion show for Williams’ latest collection with HSN. The following month, a rep for Williams denied the dating rumor in a statement to People, saying, “They are simply longtime friends.”

Drake Writes His 2016 Song ‘Too Good’ About Williams

Though we didn’t know it for sure at the time of its release, Drake’s 2016 track, “Too Good,” which features another of his exes, Rihanna, is all about Williams. Footage released in 2024 shows Drake working on the song and discussing the inspiration with his mother.

“I get heavy on a couple joints, but this is more about me and Serena,” Drake said of the track.

By the time the song is released in May 2016, Drake and Williams’ romance seems to have fizzled out. Throughout 2016, Williams and Ohanian are hinting at their romance on social media until he proposes to her in December 2016.

In 2018, Drake did show up to one of Williams’ Wimbledon matches, supporting her from the stands.

Drake Dissed Alexis Ohanian in a 2022 Track

Years after he and Williams called it quits, Drake took another swipe at his ex in his 2022 song, “Middle of The Ocean,” in which he raps, “Sidebar, Serena, your husband a groupie/He claim we don’t got a problem but/No, boo, it is, like you comin’ for sushi/We might pop up on ’em at will like Suzuki.”

Ohanian, who married Williams in 2017 after welcoming their daughter, Alexis Olympia, earlier that year, subtly responded to the diss in a tweet, writing, “It’s cliche, but life changed when I became a husband + papa. It’s made me 100x better as a man and a businessman.”

“The reason I stay winning is because I’m relentless about being the absolute best at whatever I do — including being the best groupie for my wife & daughter,” the Reddit founder concluded. Per Business Insider, Williams responded to her husband’s tweets with smiling heart emojis. 

Before you go, click to see all the celebrities at the 2025 Super Bowl.