The precise nature of Drake and Serena Williams’ supposed fling stays a thriller. What isn’t a thriller, nevertheless, is that the tennis legend has been taking on actual property within the rapper’s head for a very long time. However let’s backtrack a bit. Drake and Williams first raised eyebrows in 2011 when he began exhibiting as much as her tennis matches and enthusiastically cheering for her. Perhaps that is uncommon for a rapper, however many individuals have rooted for the GOAT.

Nonetheless, it wasn’t till Drake publicly teased Williams with a cryptic — and sexually charged — message that the rumor mill went into overdrive. “I can’t wait to place it on you and make you sweat … throughout our match this weekend,” he tweeted at her in August 2011. One thing was positively occurring. Proof of any relationship fizzled till 2015, once they had been seen kissing throughout a sushi date. Sources denied they had been in a relationship however confirmed they’d been previously whereas giving perception into their break up.

“Serena briefly dated Drake round 2011 and though it did not finish that nicely, they’ve remained mates since,” an insider informed Web page Six. That appeared to be the tip of it. Williams married Reddit co-founder Alexis Ohanian in 2017, and Drake refuses to cool down. The fling might need been temporary, but it surely clearly wasn’t meaningless. Drake has hinted he by no means actually obtained over Williams — one thing followers are at all times expecting and have noticed loads of in his lyrics.

Serena Williams has been fueling Drake’s lyrics since 2013, when he first dropped what appeared like a nod to his ex (and possibly future) fling. In “Worst Habits,” he used the athlete’s unmatched expertise to underline his personal capability to rise above his childhood difficulties, significantly rising up with out a father, to succeed in the very high. “It is gross what I internet / I am with my entire set, tennis matches on the crib / I swear I might beat Serena when she playin’ along with her left,” he wrote.

Drake was additionally apparently referencing an inside joke they’d. Williams and Drake could have appeared like an odd pair when rumors about their relationship began circulating, however they’ve extra in frequent than meets the attention. Drake really grew up taking part in tennis — which shocked even Williams. “He stated he performed tennis when he was younger. I believed, actually, of all sports activities,” she informed Canadian tennis journalist Mike McIntyre in 2015.

It seems he is fairly first rate on the recreation, which, coming from one of the best, should imply one thing. “So we hit loads,” she stated earlier than correcting herself. “Not loads. However we used to hit loads. Yeah, he is actually good.” It was throughout these matches that the within joke took place. “He says he can take me lefty, which (rolls eyes) will get me charged up,” she laughed. Proper-handed, Williams at all times needed to play along with her left. “Lefties are simply so cool. I simply love lefties,” she stated in 2014. 

Information of Serena Williams’ engagement to Alexis Ohanian seemingly hit Drake arduous. Not less than, that is what the lyrics to “Nothings into Somethings” recommend. This time, he did not simply trace on the relationship — the complete track appears to be about his heartbreak over her transferring on. “Did I simply learn that you just simply obtained engaged on me? / I heard out of your good friend, you could not even inform me / Or higher but, wait on me,” he wrote.

The lyrics are brief, with solely two verses — and each appear to trace at his relationship with Williams. “Least, do I get an invite or one thing? / A press release or one thing?” he continued within the second. In contrast to in “Worst Habits,” Drake did not point out Williams by identify. However the timeline leaves little to little question in regards to the inspiration behind the lyrics. He launched the track in March 2017, three months after Ohanian proposed to the previous world No. 1 in December 2016.

Williams’ supposed second fling with Drake appears to have overlapped along with her relationship with Ohanian, heightening the drama between the 2. She met her future husband in Italy in Could 2015, three months earlier than she was photographed kissing Drake. However, as he urged in his lyrics, he knew about Ohanian, although she seemingly downplayed the connection. “Ask about that, you’d say it was nothing / However this is one other nothin’ that you just made into somethin’ / Cannot simply go away it off that method,” he penned.

Drake took his feud with Meek Mill to the subsequent degree when he launched the diss tracks “Charged Up” and “Again to Again” in 2015, however he virtually did not. It was Serena Williams who impressed him to take action. The meat appears to have began as a result of Drake did not flip up for a present after Meek believed he had agreed to, which Drake characterised as miscommunication. After that, Meek accused Drake of ghostwriting. As an alternative of tweeting again, he wrote songs.

However doubts crept in till he and Williams began discussing her rivalry with Maria Sharapova. “She’s a high competitor, so she was like: ‘You gotta end it. I am speaking about performed — over — and it is gotta be one thing that everybody [Meek] is with, and him, have to listen to. You possibly can’t do some s**t for the second, after which it goes away.’ She kinda put this battery in my again,” he stated on the “Rap Radar” podcast in 2019, including that he was “with Serena on the time.”

Whereas the feud between the rappers is now immortalized as artwork, Drake and Meek reconciled and put their points previously. In 2018, they signaled the tip of their feud when Drake invited Meek to hitch him onstage at Boston’s TD Backyard. By 2023, they had been shut mates once more. “We obtained it like that, the place we could possibly be brutal,” he stated on “Hip Hop Nation,” referring to their honesty about one another’s music.

No proof proves that Drake was hung up on Serena Williams for some time greater than his 2016 hit track “Too Good.” In it, the rapper explored the shortage of communication typically seen when relationships are nearing their finish. “Look, I do not know speak to you / I do not know ask you in case you’re okay / My mates at all times really feel the necessity to inform me issues / Looks as if they’re simply happier than us nowadays,” the lyrics learn.

Drake additionally mentioned feeling unappreciated within the relationship, one other attribute of a doomed connection. “I am too good to you / I am method too good to you / You are taking my love as a right,” he sings within the refrain. The track’s that means is simple. What caught us all off guard was the revelation that Serena Williams impressed it, provided that neither had ever confirmed the connection. In contrast to the remainder of us, Drake’s mother, Sandi Graham, was unsurprised when he mentioned it in a clip from a studio session he launched in 2024.

“I get heavy on a pair joints, however that is extra about me and Serena,” he stated, to which his mother responded: “I gathered that.” Drake additionally shared he tries to honor the connection and his love pursuits each time he writes about them. “I do know Serena very nicely, and I do know that she’ll hear it loud and clear, however not hate me for it as a result of it is lighthearted,” he stated.

Greater than a decade after they had been linked within the early 2010s, Serena Williams continued to dwell rent-free in Drake’s head. In his 2022 track “Center of the Ocean,” he confirmed he was performed taking part in good and took a jab not at Williams however at her husband, Alexis Ohanian. “Sidebar, Serena, your husband a groupie / He declare we do not obtained an issue however / No, boo, it’s such as you comin’ for sushi,” Drake rapped. Ohanian could not keep quiet when Drake concerned him within the drama.

Whereas discussing a profile on him, he seemingly responded by utilizing the pejorative time period Drake used to check with himself. “The explanation I keep profitable is as a result of I am relentless about being the very best at no matter I do — together with being one of the best groupie for my spouse & daughter,” he wrote on X. Ohanian did not point out the rapper, however the timing leaves little room for doubt, as Ohanian’s response got here the identical day Drake launched the track.

All through Drake’s years of name-dropping Williams in songs, she stayed mum. Nonetheless, many imagine she hit Drake the place it hurts along with her cameo look throughout Kendrick Lamar’s halftime efficiency on the 2025 Tremendous Bowl (seen above). However she denied she was choosing sides amid Lamar’s and Drake’s years-long feud. “Def not dancing to be petty lol,” she tweeted. “I feel I proved 23 instances over (not counting 4 gold medals) that I merely haven’t got time for petty.”