The exact nature of Drake and Serena Williams’ supposed fling remains a mystery. What is not a mystery, however, is that the tennis legend has been taking up real estate in the rapper’s head for a long time. But let’s backtrack a bit. Drake and Williams first raised eyebrows in 2011 when he started showing up to her tennis matches and enthusiastically cheering for her. Maybe that’s unusual for a rapper, but many people have rooted for the GOAT.
However, it wasn’t until Drake publicly teased Williams with a cryptic — and sexually charged — message that the rumor mill went into overdrive. “I cannot wait to put it on you and make you sweat … during our match this weekend,” he tweeted at her in August 2011. Something was definitely going on. Evidence of any relationship fizzled until 2015, when they were seen kissing during a sushi date. Sources denied they were in a relationship but confirmed they had been in the past while giving insight into their split.
“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. That seemed to be the end of it. Williams married Reddit co-founder Alexis Ohanian in 2017, and Drake refuses to settle down. The fling might have been brief, but it clearly wasn’t meaningless. Drake has hinted he never really got over Williams — something fans are always watching for and have spotted plenty of in his lyrics.
Drake wrote a lot of songs about Serena Williams
Serena Williams has been fueling Drake’s lyrics since 2013, when he first dropped what seemed like a nod to his ex (and maybe future) fling. In “Worst Behavior,” he used the athlete’s unmatched skills to underline his own ability to rise above his childhood difficulties, particularly growing up without a father, to reach the very top. “It’s gross what I net / I’m with my whole set, tennis matches at the crib / I swear I could beat Serena when she playin’ with her left,” he wrote.
Drake was also apparently referencing an inside joke they had. Williams and Drake may have seemed like an odd pair when rumors about their relationship started circulating, but they have more in common than meets the eye. Drake actually grew up playing tennis — which surprised even Williams. “He said he played tennis when he was young. I thought, really, of all sports,” she told Canadian tennis journalist Mike McIntyre in 2015.
It turns out he’s pretty decent at the game, which, coming from the best, must mean something. “So we hit a lot,” she said before correcting herself. “Not a lot. But we used to hit a lot. Yeah, he’s really good.” It was during those matches that the inside joke came about. “He says he can take me lefty, which (rolls eyes) gets me charged up,” she laughed. Right-handed, Williams always wanted to play with her left. “Lefties are just so cool. I just love lefties,” she said in 2014.
Drake was bitter when Serena Williams got engaged
News of Serena Williams’ engagement to Alexis Ohanian seemingly hit Drake hard. At least, that’s what the lyrics to “Nothings into Somethings” suggest. This time, he didn’t just hint at the relationship — the entire song seems to be about his heartbreak over her moving on. “Did I just read that you just got engaged on me? / I heard from your friend, you couldn’t even tell me / Or better yet, wait on me,” he wrote.
The lyrics are short, with only two verses — and both seem to hint at his relationship with Williams. “Least, do I get an invitation or something? / A statement or something?” he continued in the second. Unlike in “Worst Behavior,” Drake didn’t mention Williams by name. But the timeline leaves little to no doubt about the inspiration behind the lyrics. He released the song in March 2017, three months after Ohanian proposed to the former world No. 1 in December 2016.
Williams’ supposed second fling with Drake seems to have overlapped with her relationship with Ohanian, heightening the drama between the two. She met her future husband in Italy in May 2015, three months before she was photographed kissing Drake. But, as he suggested in his lyrics, he knew about Ohanian, though she seemingly downplayed the relationship. “Ask about that, you would say it was nothing / But here’s another nothin’ that you made into somethin’ / Can’t just leave it off that way,” he penned.
Serena Williams inspired Drake to write Meek Mill’s diss tracks
Drake took his feud with Meek Mill to the next level when he released the diss tracks “Charged Up” and “Back to Back” in 2015, but he almost didn’t. It was Serena Williams who inspired him to do so. The beef seems to have started because Drake didn’t turn up for a show after Meek believed he had agreed to, which Drake characterized as miscommunication. After that, Meek accused Drake of ghostwriting. Instead of tweeting back, he wrote songs.
But doubts crept in until he and Williams started discussing her rivalry with Maria Sharapova. “She’s a top competitor, so she was like: ‘You gotta finish it. I’m talking about done — over — and it’s gotta be something that everyone [Meek] is with, and him, have to hear. You can’t do some s**t for the moment, and then it goes away.’ She kinda put this battery in my back,” he said on the “Rap Radar” podcast in 2019, adding that he was “with Serena at the time.”
While the feud between the rappers is now immortalized as art, Drake and Meek reconciled and put their issues in the past. In 2018, they signaled the end of their feud when Drake invited Meek to join him onstage at Boston’s TD Garden. By 2023, they were close friends again. “We got it like that, where we could be brutal,” he said on “Hip Hop Nation,” referring to their honesty about each other’s music.
Drake admitted Too Good is about Serena Williams
No evidence proves that Drake was hung up on Serena Williams for a while more than his 2016 hit song “Too Good.” In it, the rapper explored the lack of communication often seen when relationships are nearing their end. “Look, I don’t know how to talk to you / I don’t know how to ask you if you’re okay / My friends always feel the need to tell me things / Seems like they’re just happier than us these days,” the lyrics read.
Drake also discussed feeling unappreciated in the relationship, another characteristic of a doomed connection. “I’m too good to you / I’m way too good to you / You take my love for granted,” he sings in the chorus. The song’s meaning is straightforward. What caught us all off guard was the revelation that Serena Williams inspired it, given that neither had ever confirmed the relationship. Unlike the rest of us, Drake’s mom, Sandi Graham, was unsurprised when he discussed it in a clip from a studio session he released in 2024.
“I get heavy on a couple joints, but this is more about me and Serena,” he said, to which his mom responded: “I gathered that.” Drake also shared he tries to honor the relationship and his love interests whenever he writes about them. “I know Serena very well, and I know that she’ll hear it loud and clear, but not hate me for it because it’s lighthearted,” he said.
Drake is STILL writing about Serena Williams
More than a decade after they were linked in the early 2010s, Serena Williams continued to live rent-free in Drake’s head. In his 2022 song “Middle of the Ocean,” he showed he was done playing nice and took a jab not at Williams but at her husband, Alexis Ohanian. “Sidebar, Serena, your husband a groupie / He claim we don’t got a problem but / No, boo, it is like you comin’ for sushi,” Drake rapped. Ohanian couldn’t stay quiet when Drake involved him in the drama.
While discussing a profile on him, he seemingly responded by using the pejorative term Drake used to refer to himself. “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,” he wrote on X. Ohanian didn’t mention the rapper, but the timing leaves little room for doubt, as Ohanian’s response came the same day Drake released the song.
Throughout Drake’s years of name-dropping Williams in songs, she stayed mum. However, many believe she hit Drake where it hurts with her cameo appearance during Kendrick Lamar’s halftime performance at the 2025 Super Bowl (seen above). But she denied she was picking sides amid Lamar’s and Drake’s years-long feud. “Def not dancing to be petty lol,” she tweeted. “I think I proved 23 times over (not counting 4 gold medals) that I simply don’t have time for petty.”
