It was 2015, and the air in Cincinnati was thick with more than just summer humidity. TMZ cameras caught something that basically broke the internet before "breaking the internet" was even a tired cliché: Serena Williams and Drake, tucked away in a private room at a high-end Italian joint called Sotto, getting very cozy.
We aren't talking about a polite "congrats on the win" handshake. They were caught in an intense make-out session. For fans who had been tracking the Serena Williams and Drake dating rumors since 2011, this was the "smoking gun" moment.
But if you look at how it all ended—with diss tracks, "groupie" allegations against her husband, and a Super Bowl Crip Walk—the story is way messier than a simple dinner date.
The 2011 Spark and the "Family" Excuse
The timeline actually starts way back in 2011. Drake started showing up at tennis matches. Not just the big ones, but a lot of them. He was sitting in the player's box, looking stressed, and tweeting things like, "@SerenaWilliams I cannot wait to put it on you and make you sweat... during our match this weekend."
People talked. Obviously.
When reporters finally cornered Serena at a press conference to ask if she was dating the biggest rapper in the world, she gave the classic celebrity pivot. She called him "family."
"We've been friends for like, so many years," she said. "Just like family."
Most people didn't buy it. You don't usually fly across the world to watch your "family" hit a yellow ball for three hours while wearing a look of sheer romantic agony.
That Messy 2015 Summer
By 2015, the friendship had clearly shifted. Drake was everywhere Serena was. He was at Wimbledon. He was in Cincinnati. He was front row at her HSN Fashion Show during New York Fashion Week.
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Then came the Sotto photos.
The images showed Serena sitting on Drake's lap, arms around his neck, in a corner booth that wasn't nearly as private as they hoped. It felt like the official debut of a power couple. But just as quickly as it peaked, it fizzled. By the end of 2015, Serena had met Reddit co-founder Alexis Ohanian.
By 2016, she was engaged.
Drake, in true Drake fashion, didn't just move on quietly. He went to the studio.
The Lyrics: When "Too Good" Got Personal
Honestly, if you want to know what happened between them, you just have to listen to the music. In 2016, Drake released "Too Good" with Rihanna. For years, fans speculated it was about Serena.
He eventually confirmed it.
In a video that surfaced later, he told his mom, Sandi Graham, that the song was about him and Serena. The lyrics are pretty biting: "I'm too good to you / I'm way too good to you / You take my love for granted / I just don't understand it."
It suggests a classic "it's complicated" ending where he felt undervalued. He even rapped about her in "Worst Behavior," joking that he could beat her if she played with her left hand. It was playful then. It got petty later.
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The "Groupie" Comment and the Husband's Response
Fast forward to 2022. Serena is long retired, a mother of two, and happily married. Drake drops the track "Middle of the Ocean."
Out of nowhere, he raps: "Sidebar, Serena, your husband a groupie / He claim we don't got a problem but / No, boo, it is like you coming for sushi."
It was a weird, unprovoked shot at Alexis Ohanian. Why call a tech mogul a groupie seven years after the relationship ended?
Alexis didn't miss a beat. He hopped on X (formerly Twitter) and posted: "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 and daughter."
It was a masterclass in taking the power out of an insult. But it proved that the Serena Williams and Drake dating history still had a lot of unresolved energy behind it.
The Super Bowl and the "Not Like Us" Moment
In February 2025, the drama hit a fever pitch during the Super Bowl halftime show. Kendrick Lamar was performing "Not Like Us"—a song specifically designed to dismantle Drake's reputation.
And there was Serena.
She didn't just stand there. She did the Crip Walk on stage while the song played. To anyone following the beef, it looked like she had officially picked a side in the Kendrick vs. Drake war.
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Later, in an interview with Time, Serena tried to play it cool. She said it wasn't shade. She said it was "sad" that people thought she was mocking her ex. "I have never had negative feelings towards him," she claimed.
But then, in November 2025, Drake "liked" an Instagram comment calling Sexyy Red a "Serena Williams upgrade" under a tennis-themed photoshoot.
The "just family" narrative is officially dead.
What Most People Get Wrong
People think this was a one-off fling. It wasn't. It was a four-year, on-and-off saga that influenced some of the biggest songs of the 2010s.
Drake didn't just date her; he seemed to be genuinely inspired by her competitive drive. He even credited her for helping him write "Back to Back," his famous diss track against Meek Mill. He said she was the one who told him he had to "finish" the beef and not let it go.
Irony is a funny thing. The woman who taught him how to win a rap war ended up dancing to his downfall on the world's biggest stage.
Timeline of the Major Beats
- 2011: First sightings at matches; the infamous "make you sweat" tweet.
- 2013: Drake mentions her "left hand" in "Worst Behavior."
- August 2015: The Cincinnati make-out photos go viral.
- September 2015: Drake sits front row at Serena’s fashion show.
- Late 2015: The split occurs; Serena begins dating Alexis Ohanian.
- 2016: Drake releases "Too Good," later confirming it's about Serena.
- 2022: Drake calls Alexis a "groupie" on "Middle of the Ocean."
- February 2025: Serena performs at the Super Bowl during Kendrick's set.
- November 2025: Drake likes a "Serena upgrade" comment on Instagram.
If you’re looking for a clean ending to the story of Serena Williams and Drake dating, you won't find one. It’s a decades-long arc of mutual admiration that curdled into public pettiness.
To see the full impact of this relationship, listen to Drake’s Views album with the context that many of the songs about "unrequited effort" are aimed at a 23-time Grand Slam champion. Then, watch Serena's ESPY monologue from 2024, where she warned people not to pick a fight with Kendrick Lamar. The subtext is loud.
Don't just take the "they're friends" quotes at face value. Look at the actions. From the tennis courts of Wimbledon to the sidelines of the Super Bowl, this is a story about two GOATs who simply couldn't figure out how to be in the same room once the romance died.
Keep an eye on Drake's future "finsta" posts. If his recent behavior is any indication, he isn't quite done talking about the one who got away to the guy he calls a groupie.