If you were scrolling through social media during the 2025 Super Bowl halftime show, you saw it. Serena Williams, the greatest of all time, doing a Crip Walk on stage while Kendrick Lamar performed "Not Like Us." The crowd lost it. But for people who remember the early 2010s, that wasn't just a dance. It was a statement. A very loud, very public exclamation point on a decade-long saga.
Honestly, the Drake and Serena Williams dating rumors have always been one of those "if you know, you know" situations in Hollywood. They never walked a red carpet as a formal couple. They never gave a joint interview to Vogue. Instead, we got years of courtside sightings, sweaty restaurant photos in Cincinnati, and some of the most pointed song lyrics in modern rap history.
It wasn't just a fling. It was a collision of two worlds: the peak of professional tennis and the rise of a rap superstar who thrives on wearing his heart—and his grudges—on his OVO-branded sleeve.
The 2011 Spark and the Common Feud
It basically all started around 2011. Drake was becoming Drake, and Serena was already a legend. People started noticing him at her matches. Not just the big ones, but the random ones where celebrities usually don't show up. Then came the tweet. Drake posted to Serena, "I cannot wait to put it on you and make you sweat... during our match this weekend."
Playful? Sure. But the industry noticed.
📖 Related: Erik Menendez Height: What Most People Get Wrong
Interestingly, this is where things got messy with Common. The Chicago rapper had dated Serena before, and suddenly, he and Drake were trading shots. Common later admitted on the Sway in the Morning show that his beef with Drake was almost entirely about their shared interest in Serena. Imagine being so iconic that two Grammy winners start a rap war over you. That's Serena.
The 2015 "Cuddling" Photos and the U.S. Open
Fast forward to 2015. This was the peak. If you were looking for evidence of Drake and Serena Williams dating, the paparazzi delivered. They were caught at a high-end Italian restaurant in Cincinnati, looking very much like a couple. Drake was also a permanent fixture in her player's box during the U.S. Open that year.
Fans actually blamed him when she lost. The "Drake Curse" became a meme because people thought his presence was distracting her from the Grand Slam.
What the Lyrics Told Us
Drake has always been a "journal rapper." He processes his life through his verses, and Serena is all over his discography.
👉 See also: Old pics of Lady Gaga: Why we’re still obsessed with Stefani Germanotta
- "Worst Behavior" (2013): "I’m with my whole set, tennis matches at the crib. I swear I could beat Serena when she playin’ with her left."
- "Too Good" (2016): This is the big one. Drake later told his mother, Sandi Graham, in a recorded conversation that this song was about Serena. The lyrics "I'm too good to you / You take my love for granted" suggest things didn't end on the best terms.
- "Nothings into Somethings" (2017): Released right after she got engaged to Alexis Ohanian. He raps about an ex getting engaged without telling him. "Did I just read that you just got engaged on me?"
The "Groupie" Comment and the Husband's Response
By 2022, most people thought the drama was dead. Serena was happily married to Reddit co-founder Alexis Ohanian. They had a daughter. Life was good. Then Drake dropped Her Loss.
On the track "Middle of the Ocean," Drake took a direct shot at Ohanian: "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 weird. It was petty. It was classic Drake.
Ohanian didn't stay quiet. He posted a photo of himself with his wife and daughter, saying he’s the "best groupie" for them because he's relentless about being the best at whatever he does. Serena replied with heart emojis.
Why the Super Bowl Moment Mattered
When Serena showed up for Kendrick Lamar's halftime show in February 2025, she wasn't just supporting a friend. Kendrick and Drake had just finished the most explosive rap feud of the decade. By dancing to "Not Like Us"—a song that systematically deconstructed Drake's character—Serena effectively picked a side.
✨ Don't miss: Brad Pitt and Angelina Jolie: What Really Happened Behind the Scenes in 2026
She later told Time magazine that she has "never had negative feelings" towards Drake and that they've known each other for years. But she also noted that "none of us... should ever pick a fight with Kendrick Lamar."
The Evolution of Their Connection
- 2011: The initial rumors and the "sweat" tweet.
- 2012: The Drake vs. Common beef.
- 2015: The Cincinnati restaurant photos and the U.S. Open sightings.
- 2016: "Too Good" is released; Serena meets Alexis Ohanian.
- 2022: The "groupie" diss on Her Loss.
- 2025: The Super Bowl Crip Walk heard 'round the world.
The Takeaway for Fans
What can we actually learn from the Drake and Serena Williams dating history?
First, never underestimate the power of a "situationship" to fuel a decade of art. Drake's best work often comes from his inability to let go of the past. Second, Serena Williams is the master of the "quiet clapback." She doesn't need to write a diss track. She just needs to show up, look incredible, and dance to the song that's currently topping the charts at her ex's expense.
If you're following these types of celeb stories, the best move is to look at the lyrics. Rappers often tell you exactly who they are crying over if you listen closely enough.
Keep an eye on Drake’s next project. After the 2025 Super Bowl, there’s almost certainly a "tennis-themed" subliminal line coming in his next album. He just can't help himself.
To get the full context of this rivalry, you should go back and listen to "Too Good" and then watch the 2025 halftime show footage. The contrast is the story.