If you were watching the 2025 Super Bowl halftime show, you saw it. Serena Williams—the GOAT of tennis—was on stage crip-walking to Kendrick Lamar’s "Not Like Us." It wasn't just a dance. It was a moment that basically set the internet on fire because, well, the history between Serena and Drake is long, messy, and mostly told through song lyrics and courtside paparazzi shots.
People have been asking the same question for over a decade: how long did serena and drake date?
The answer isn't a simple "June to July." It’s more like a four-year window of "are they or aren't they" that stretched from 2011 to late 2015. They were the ultimate "it" couple that never actually admitted they were a couple.
The 2011 Spark: It Started With a Tweet
Everything kicked off back in August 2011. Drake, who was already becoming the "King of Emotional Rap," tweeted something pretty bold at Serena. He told her he couldn't wait to "make her sweat" during their tennis match that weekend.
Subtle? Not really.
Shortly after that, he was spotted in the stands at the Canadian Open. He wasn't just there for the sport; he was there for her. Insiders at the time said they were "briefly dating" during that summer, but it seemingly fizzled out as fast as it started.
Why it didn't last the first time
Rumors suggested that the timing just wasn't right. Serena was focused on her comeback, and Drake was busy becoming a global superstar. By 2012, the buzz had died down. Serena was linked to her coach, Patrick Mouratoglou, and Drake was... well, being Drake.
But rappers don't just forget.
In 2013, Drake dropped "Worst Behavior." He rapped about being at "tennis matches at the crib" and joked that he could beat Serena even if she played with her left hand. It was a lighthearted jab, but it proved she was still very much on his mind. Honestly, it’s kinda classic Aubrey.
The 2015 Comeback: The Kiss Heard 'Round the World
If 2011 was the spark, 2015 was the full-blown wildfire. This is the year most people think of when they ask how long did serena and drake date.
Throughout that summer, Drake was a permanent fixture at Serena’s matches. He was at Wimbledon. He was at the Western & Southern Open in Cincinnati. People were whispering, but Serena kept it cool. During a press conference in July 2015, a reporter asked point-blank about their status.
"We've been friends for like, so many years," she said. "Just like family."
That "family" excuse didn't last long. In August 2015, TMZ published photos of the two of them looking very cozy at a high-end Italian restaurant in Cincinnati. We’re talking full-on making out in a private room. You don't do that with "family."
The "Too Good" Era
This second stint was intense but short. Drake was there for her HSN Fashion Show in September 2015, sitting front row next to Anna Wintour. He was her biggest cheerleader.
But by October, things cooled off.
We later found out through Drake’s own mouth—specifically in the "100 Gigs" footage released in 2024—that his hit song "Too Good" was specifically about Serena. In a video with his mom, Sandi Graham, he admits the song is about him and the tennis star.
The lyrics tell a story of a guy who feels like he’s giving way more than he’s getting:
- "I'm too good to you"
- "You take my love for granted"
- "I just don't understand it"
It sounds like Drake felt slighted. Maybe he wanted a commitment she wasn't ready to give. By the end of 2015, the "relationship" was effectively over. Serena met Reddit co-founder Alexis Ohanian in Rome later that year, and the rest is history.
The "Groupie" Comment and the Fallout
Even though they stopped "dating" in 2015, the drama didn't stop. Drake has a habit of checking in on his exes via his lyrics. In 2022, he dropped "Middle of the Ocean" and took a direct shot at Serena’s husband, Alexis Ohanian.
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He rapped: "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 jab. Alexis took it in stride, tweeting that he stays winning because he’s the "best groupie" for his wife and daughter. Serena even backed him up with heart emojis. It was pretty clear whose side she was on.
Summary of the Serena and Drake Timeline
To make it easy to track, here is the rough breakdown of their history:
- 2011: The initial spark. Flirty tweets, courtside appearances, and a brief summer romance.
- 2013: Lyrical references in "Worst Behavior" suggest they stayed in touch.
- 2015 (The Peak): Spotted kissing in Cincinnati. Drake attends all her major matches. This lasted about 4–6 months.
- 2016: Drake releases "Too Good," effectively confirming the relationship was a struggle for him.
- 2017: Serena marries Alexis Ohanian.
- 2022: Drake disses Alexis on "Middle of the Ocean."
- 2025: Serena joins Kendrick Lamar on stage to dance to a Drake diss track.
Why it matters now
The reason this is still a topic of conversation in 2026 is that it represents a rare moment where Serena Williams let her guard down in the public eye. She’s usually incredibly private. Drake, on the other hand, is an open book of petty grievances and "what ifs."
Their "relationship" likely totaled about a year of actual dating spread across two different periods.
If you're looking for lessons here, it’s probably that some people are better as "longtime friends" than partners. Drake seemed to want the "Superstar Power Couple" narrative, while Serena clearly found her peace with someone who was happy to be her "groupie" in the stands.
To see the evolution of this story for yourself, you should go back and listen to "Too Good" followed by "Not Like Us." The shift in energy from Drake's perspective to Serena's 2025 stage appearance tells you everything you need to know about where they stand today. Check out Serena's recent interviews where she discusses "choosing happiness" to get the full picture of her life post-2015.