If you were watching the Super Bowl halftime show in 2025, you saw it. Serena Williams wasn't just there; she was there, C-walking on stage while Kendrick Lamar performed "Not Like Us." For the uninitiated, it was a cool dance. For anyone who followed the messy, decade-long history of Drake and Serena Williams together, it was a nuclear-grade peace of shade.
Honestly, the timeline of these two is weird. It’s not your typical "we dated and moved on" celebrity story. It’s a mix of courtside puppy love, "too good" excuses, and a very public beef with a Reddit co-founder.
The Cincinnati Photos That Changed Everything
Back in August 2015, the internet basically broke. TMZ published photos of Drake and Serena Williams together at Sotto, an Italian restaurant in Cincinnati. They weren't just eating pasta. They were caught in a full-blown make-out session in a private back room after Serena won the Western & Southern Open.
The photos were blurry, grainy, and unmistakable. At the time, Serena was chasing the elusive calendar-year Grand Slam. Drake was everywhere. He was at Wimbledon sitting next to Venus. He was in the stands in Toronto. He even followed her to a suburb in Ohio just to watch her play.
People close to Serena’s camp tried to play it cool. Her reps told People they were just "longtime friends." But friends don’t usually do tequila shots and heavy PDA in the back of an upscale eatery while six other people watch.
Before the "Official" Hookup
Actually, this didn't start in 2015. You have to go back to 2011. That's when the rumors first bubbled up. Drake was tweeting her, saying he couldn't wait to "make her sweat" during a tennis match.
It even sparked a bizarre feud between Drake and the rapper Common. Common had dated Serena previously, and he wasn't exactly thrilled about the "6 God" moving in on his old turf. It led to the track "Sweet," where Common took shots at Drake for being soft. Looking back, it was probably the first time Drake realized that being linked to the greatest female athlete of all time comes with a specific kind of pressure.
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Did He Really Write "Back to Back" Because of Her?
One of the wildest details of the Drake and Serena Williams together era is her influence on his music. We aren't just talking about love songs. We’re talking about war.
In 2015, Drake was in the middle of a career-defining beef with Meek Mill. He revealed later on the Rap Radar podcast that Serena was actually with him while he was writing "Back to Back."
Think about that.
The greatest tennis player in history was giving him competitive advice. She told him he had to finish it. She compared the rap battle to her rivalry with Maria Sharapova—the idea that you can't just do something for the moment; you have to end the conversation. She "put a battery in his back," according to Drake himself.
The "Too Good" Confession and the Shift to "Groupie" Talk
By 2016, the vibe shifted. Serena met Alexis Ohanian in Rome. Suddenly, Drake was out, and the tech mogul was in.
Drake didn't take it quietly. In his track "Too Good" with Rihanna, he sings about being "too good" to someone who takes his love for granted. In the 100 Gigs archival footage released recently, he’s seen talking to his mom, Sandi Graham, specifically saying that the song is about Serena.
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"I know Serena very well and I know she'll hear it loud and clear, but she'll also not hate me for it because it's lighthearted."
Well, maybe she didn't hate it then, but things got petty fast. By 2022, Drake dropped "Middle of the Ocean." In it, he called Serena’s husband, Alexis Ohanian, a "groupie."
“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 line. Alexis, being the internet-savvy guy he is, clapped back by saying he’s the "best groupie" for his wife and daughter. Serena didn't say a word, but she did drop a bunch of heart-eye emojis on her husband's post.
Why We Are Still Talking About This in 2026
You'd think after a marriage and two kids, the Drake and Serena Williams together narrative would be dead. It’s not.
Serena’s 2025 Super Bowl appearance proved that. By dancing to "Not Like Us"—a song that decimated Drake’s reputation during his beef with Kendrick Lamar—she basically picked a side. She even joked at the ESPYs that nobody should ever pick a fight with Kendrick.
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It feels like a final "game, set, match."
What You Should Know About the Timeline
- 2011: First dating rumors and the Common beef.
- 2013: Drake mentions her in "Worst Behavior" (the "playing with her left" line).
- 2015: The Cincinnati make-out photos and the U.S. Open appearances.
- 2016: The release of "Too Good" and Serena’s engagement to Alexis.
- 2022: The "groupie" diss in "Middle of the Ocean."
- 2025/2026: Serena's public support for Kendrick Lamar.
The Reality of the "Power Couple" That Wasn't
Looking back, it’s clear Drake was way more invested in the public "power couple" image than Serena was. While Drake was trailing her around Wimbledon like a puppy (as observers at the time described it), Serena was focused on her legacy.
She was at the peak of her "Serena Slam" journey. Drake was a fun distraction, a cheerleader, and maybe a brief flame. But the moment she moved on, it seemed like he couldn't let the "L" go.
If you're looking for lessons in all this, it’s pretty simple:
- Don't talk about the husband. Drake's decision to bring Alexis into the lyrics is what turned a dormant friendship into a cold war.
- Competition is internal. Serena used her competitive drive to help Drake win a rap battle, then used that same drive to protect her peace later on.
- The internet never forgets. Those 2015 photos are still the primary evidence used by fans to explain why Drake still seems a bit salty a decade later.
If you want to understand the current state of Drake's relationships with his peers, looking at his history with Serena is a great blueprint. It shows the transition from being the "ultimate insider" to someone who eventually gets left out of the circle when the vibe changes.
Next Steps for Fans:
- Check out the 100 Gigs footage to hear Drake’s raw thoughts on "Too Good."
- Listen to "Middle of the Ocean" and "Nothings Into Somethings" back-to-back to hear the progression of his frustration.
- Re-watch the 2025 halftime show if you want to see exactly how Serena feels about the situation today.