It was the summer of 2015, and the air in Cincinnati was thick with more than just humidity. If you were following tennis—or just keeping an eye on TMZ—you probably remember the blurry photos. Drake and Serena Williams. Tucked into a corner booth at Sotto, a trendy Italian spot downtown. They weren't just "grabbing a bite." They were full-on making out.
For years, people have asked: did they actually date? Or was it just one of those high-profile flings that rappers love to brag about and athletes prefer to forget?
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Honestly, it’s complicated. Like, "multiple-diss-tracks-and-a-Super-Bowl-crip-walk" complicated. While Serena has mostly kept her cool, Drake has spent the better part of a decade dropping crumbs in his lyrics, basically proving that he never quite got over the Greatest of All Time.
The Timeline: From Courtside Flirts to Dinner Dates
The rumors didn't actually start in 2015. They go way back to 2011. Drake was a regular fixture in Serena’s player box, which is basically the celebrity equivalent of "it's official" in the tennis world. He was there at the Canadian Open in Toronto, looking more like a superfan than a platinum-selling artist.
He even tweeted at her back then, making some pretty suggestive jokes about putting it on her and making her "sweat" during a match. It was thirsty. Very thirsty.
But then things went quiet for a bit. Serena was linked to her coach, Patrick Mouratoglou, and Drake was busy being, well, Drake. It wasn't until that 2015 Cincinnati win—and the subsequent U.S. Open—that the fire really caught. Drake was everywhere. He was at her fashion shows. He was at her matches. He was reportedly the "battery in her back" when she was dealing with her rivalry against Maria Sharapova.
In fact, Drake later admitted on the Rap Radar podcast that he was with Serena when he wrote "Back to Back," his infamous Meek Mill diss. He said she was the one pushing him to finish it, telling him he had to make it something that would last. Imagine being one of the greatest rappers on the planet and having Serena Williams—the woman who dominated center court for twenty years—telling you to go for the jugular. That's a lot of pressure.
Why the Serena Williams and Drake Romance Fizzled
So, what went wrong? Basically, Alexis Ohanian happened.
While Drake was busy being a "superfan" in the stands, Serena was secretly meeting the co-founder of Reddit at a hotel in Rome. It’s kind of a legendary "meet-cute." She tried to tell him there was a rat near his table to get him to move; he didn't care. That was May 2015.
By the end of that year, the Drake sightings stopped. By December, Serena was appearing at the Sports Illustrated Sportsperson of the Year banquet with Alexis as her plus-one.
Drake didn't take it well. Or at least, his music suggests he didn't.
The Lyrics That Told the Story
If you want to know how Drake felt, you just have to listen to the tracks. He’s never been one for subtlety.
- "Worst Behavior" (2013): He bragged about beating Serena even if she played with her left hand.
- "Too Good" (2016): He later told his mom on a leaked studio clip (the "100 Gigs" drop) that this song was specifically about him and Serena. The hook—I’m too good to you / I’m way too good to you—suddenly sounds a lot more bitter when you realize it’s aimed at a woman who chose a "tech nerd" over him.
- "Nothings into Somethings" (2017): He raps about an ex getting engaged without telling him. Given the timing of Serena’s engagement to Alexis, the math isn't hard to do.
The "Groupie" Comment and the 2025 Super Bowl
Fast forward to 2022. Most people would have moved on by now, right? Not Drake. On the track "Middle of the Ocean," he took a direct shot at Serena’s husband: "Sidebar, Serena, your husband a groupie."
It was a weird move. Petty? Definitely. Alexis, for his part, handled it with a level of class that made Drake look even smaller. He tweeted that he’s happy to be a "groupie" for his wife and daughter.
But the real "mic drop" moment came during the 2025 Super Bowl.
When Kendrick Lamar took the stage for the halftime show—right in the middle of his massive beef with Drake—who showed up? Serena. Not only did she show up, she danced to "Not Like Us," the ultimate Drake diss track.
She later tried to downplay it in an interview with Time, saying it wasn't intended as shade and that she’s known Drake for years. But come on. You don’t get on that stage, in that moment, unless you’re sending a message.
What This Tells Us About Celebrity "Friendships"
What most people get wrong about Serena Williams and Drake is thinking it was a massive, years-long relationship. In reality, it was likely a period of "situationship" intensity followed by a very long, very one-sided musical aftermath.
Serena moved on to build a family and a business empire. Drake... well, he kept writing songs.
It’s a classic case of what happens when a "top competitor" (Drake's words for Serena) meets someone who isn't intimidated by her success but also isn't trying to outshine it. Drake is a star. He wants to be the center of the universe. Alexis Ohanian seems perfectly happy being the guy holding the camera while Serena wins.
Key Takeaways for the Curious:
- Watch the Lyrics: If you’re a fan of Drake’s Views or More Life eras, go back and listen with Serena in mind. It changes the vibe of the songs entirely.
- The "Hometown" Rule: Notice how Serena's 2024 ESPYs hosting gig included a joke about Drake being "Forrest Gump-ed" out of Toronto. She knows how to play the game.
- Separate the Art from the Reality: Just because Drake says they were "together" doesn't mean Serena viewed it as a committed relationship. She famously called him "just like family" in a 2015 press conference. Ouch.
If you’re looking to understand the full scope of their history, the best thing you can do is look at the 2015 U.S. Open photos versus the 2017 wedding photos. The contrast tells you everything you need to know about why one stayed a "rumor" and the other became a life.
Stop looking for a "hidden chapter" and start looking at the scoreboard. Serena won this round, and she didn't even have to release a diss track to do it.
Next Steps for You: Check out the lyrics to "Too Good" and "Middle of the Ocean" side-by-side. You'll see the shift from "I love you" to "I’m bitter" in real-time. Also, keep an eye on Alexis Ohanian’s social media—he’s still the king of the subtle clapback whenever Drake’s name comes up in connection to his wife.