Honestly, if you blinked at the wrong time between 2011 and 2015, you probably missed the height of the drama. But the internet never forgets. People are still obsessing over Serena Williams ex boyfriend Drake because the story didn’t just end with a breakup; it spilled over into diss tracks, Reddit-thread defenses, and a very public crip walk at the Super Bowl.
It’s one of those Hollywood—or maybe sports-meets-hip-hop—mysteries. Neither of them ever sat down for a "tell-all" interview while they were together. But the evidence was everywhere. From the courtside seats at Wimbledon to the backroom of an Italian restaurant in Cincinnati, the "6 God" and the GOAT were definitely more than just friends.
The Cincinnati "Make-Out" and the Wimbledon Puppy Dog Phase
Let’s go back to 2015. This was the year it all became undeniable. For months, rumors had been swirling. Drake was suddenly the biggest tennis fan on the planet. He wasn't just showing up to the big matches; he was "shlepping," as some reporters put it, to random suburbs in Ohio just to watch Serena play.
The breaking point was Sotto. It's this upscale Italian spot in downtown Cincinnati. Just hours after Serena dominated the WTA tournament there, she and Drake were caught in a private back room. Only it wasn't that private. Someone snapped photos of them basically all over each other. Tequila shots were involved. It was intense.
But even before the "Cincinnati incident," Drake was acting like a total fanboy. At Wimbledon that same year, he was spotted trailing her around the facilities like a puppy. He was even sitting in her player box, right next to her sister Venus. It was a weird mix of high-stakes sports and high-profile romance.
Why the timeline is so messy
Things get confusing because Serena met her now-husband, Alexis Ohanian, right around this same period.
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- 2011: First reports of Drake and Serena dating surface. Drake tweets some suggestive stuff about making her "sweat" during a match.
- 2013: Drake releases "Worst Behavior" with the line, "I swear I could beat Serena when she playin' with her left."
- 2015: The peak. Wimbledon, Cincinnati, and then Drake attending her HSN fashion show.
- Late 2015: Suddenly, Alexis Ohanian is the one showing up as her plus-one.
It felt like a whirlwind. One minute Drake is the main character in her life, and the next, he's relegated to a lyrical footnote.
Serena Williams ex boyfriend Drake and the "Too Good" Confession
For a long time, we only had guesses. Then, Drake basically confirmed the whole thing through his music. It's kind of his brand, right? In 2024, some old studio footage leaked where he’s talking to his mom, Sandi Graham. He’s playing his song "Too Good" (the one with Rihanna) and he straight-up tells his mom, "This is more about me and Serena."
His mom’s response? "I gathered that."
The lyrics in that song are pretty stinging if you look at them now. "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 paints a picture of a guy who felt rejected. While the world saw Drake as this huge superstar, in Serena’s world, he was just another guy who couldn't keep up with her pace.
The "Back to Back" Connection
Here’s a detail most people miss: Serena actually helped Drake during his legendary feud with Meek Mill. Drake revealed on the Rap Radar podcast that he was with Serena when he was writing "Back to Back."
They were talking about her rivalry with Maria Sharapova. Serena, being the ultimate competitor, told him, "If you're gonna go again, you gotta finish it." She basically gave him the "killer instinct" he needed to win that rap battle. It makes you wonder if that's why Drake felt so "taken for granted" later on—he felt like he'd been her student in the art of war.
When things got petty: "Your husband a groupie"
Fast forward to 2022. Serena has been happily married to Alexis Ohanian for years. They have kids. They’re a tech-power couple. Most people assumed the Drake thing was ancient history.
Then Drake drops "Middle of the Ocean."
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." Ouch. It was such a random, unprovoked shot. It felt like Drake was still holding onto something from seven years prior. Alexis, being the king of "internet dad" energy, didn't take the bait. He actually leaned into it. He tweeted that he’s happy to be the "best groupie" for his wife and daughter. Serena even responded with heart emojis.
The Super Bowl 2025 Statement
If you think Serena didn't notice the "groupie" comment, you don't know Serena. In 2025, when Kendrick Lamar headlined the Super Bowl—right in the middle of his massive beef with Drake—Serena appeared on stage.
She didn't say a word. She just crip-walked to "Not Like Us."
For anyone who follows the Serena Williams ex boyfriend Drake saga, it was the ultimate "mic drop" moment. She was siding with the guy who effectively ended Drake's "invincible" era. Even though she later told Time magazine that she "never had negative feelings" toward Drake and the dance was just a tribute to her hometown of Compton, the timing was too perfect to be an accident.
What we can learn from the "Drizzy-Serena" era
Relationships in the public eye are complicated, but this one was especially strange because of the power dynamic. Serena was—and is—a global icon. Drake is a titan in music. When those two worlds collided, it wasn't about "clout"; it was about two people at the top of their games trying to see if they fit.
They didn't.
Takeaways for the fans:
- Watch the lyrics: Most of Drake's 2015-2016 catalog has Serena's DNA all over it.
- Competitors stay competing: Serena’s influence on "Back to Back" shows that her winning mentality applies to everything, even hip-hop beef.
- Class wins: While Drake took shots years later, Serena and Alexis chose to handle it with humor and a high-profile stage presence.
If you’re looking to dive deeper into this, check out Drake’s 100 Gigs archive. There’s a lot of raw footage from that era that shows just how much he was inspired by his time with her. It’s a fascinating look at a relationship that was never "official" but was clearly life-changing for the rapper.
The next time you hear "Too Good" on the radio, just remember: that's not just a pop song. It's a diary entry about the greatest tennis player to ever pick up a racket.
Actionable Insights:
- Listen to "Too Good" and "Middle of the Ocean" back-to-back to hear the shift from heartbreak to pettiness.
- Follow Alexis Ohanian on X to see how he continues to use the "groupie" label as a badge of honor for supporting his family.
- Watch the 2015 Cincinnati footage if you can find it—it’s the only time they truly let the guard down in public.