If you watched the 2025 Super Bowl halftime show, you probably saw something that made you do a double-take. Serena Williams, the undisputed GOAT of tennis, wasn’t just sitting in a VIP box. She was on stage, dancing and crip-walking to Kendrick Lamar’s "Not Like Us"—a song specifically designed to dismantle Drake’s reputation.
It was a loud, public moment that felt like a final exhale after years of subtle tension. But for younger fans or those who don't spend their lives refreshing TMZ, it raised a massive question: wait, how long did drake and serena date, and why is there still so much smoke between them over a decade later?
Honestly, their history is way messier than most people realize. It wasn’t just a quick summer fling; it was a years-long saga of court-side flirting, secret songs, and a relationship that officially flared up twice.
The First Set: 2011 and the Twitter Fingers
The sparks didn’t start in a dark club; they started on Twitter and in the stands of professional tennis tournaments. Back in 2011, Drake was just becoming the global superstar we know now, and he made no secret of his crush.
He was spotted at several of Serena's matches that year. It wasn't just a casual "I like tennis" thing, either. The guy was intense. He even tweeted at her in 2011, saying he couldn’t wait to "make her sweat" during a match. Cheesy? Definitely. But it worked.
The two were rumored to be dating for a few months during that 2011 stretch. However, it didn't last long the first time around. By the end of the year, things had cooled off, and the rumors died down. They reportedly stayed "friends," but as we’ve seen with Drake’s track record, "friends" often means "wait until I write a song about this."
The Common Factor
It's worth noting that this first stint caused some major ripples in the rap world. Rapper Common, who had previously dated Serena, wasn't exactly thrilled with Drake moving in. This actually sparked one of Drake's earliest beefs, leading to the track "Stay Schemin’" where Drake took shots at Common.
Even then, Serena was at the center of hip-hop drama without ever saying a word.
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The 2015 Comeback: When It Got Serious
For about three years, things were quiet. Then came 2015. This is the era most people remember because the proof became impossible to ignore.
In August 2015, the internet nearly broke when photos surfaced of Drake and Serena "making out" at a restaurant called Sotto in Cincinnati. This wasn't a grainy "maybe it's them" photo. It was clear. They were definitely together.
For a few months that summer and fall, it looked like they were the next big power couple. Drake was a permanent fixture in her player’s box. He was there for her Wimbledon victory. He was there for the U.S. Open. He was even front row at her HSN Fashion Way show in September 2015, looking like the ultimate supportive boyfriend.
So, how long did drake and serena date in total?
If you add up the 2011 stint and the 2015 resurgence, you’re looking at two distinct windows of several months each, totaling maybe a year of "official-unofficial" dating spread across a four-year timeline.
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Why "Too Good" Changed Everything
Drake eventually confirmed the relationship in the most Drake way possible: through a song. In the 2024 "100 Gigs" data dump, behind-the-scenes footage revealed Drake telling his mother, Sandi Graham, that his hit song "Too Good" (featuring Rihanna) was actually about Serena.
He told his mom:
"I get heavy on a couple joints, but this is more about me and Serena."
The lyrics "I’m too good to you / I’m way too good to you / You take my love for granted" suddenly took on a very different meaning. While the world thought he was pining over Rihanna, he was actually frustrated with the tennis star.
The Breakup and the Ohanian Era
The 2015 romance didn't survive the winter. By late 2015, things had fizzled out for good.
Serena moved on quickly—and successfully. She met Reddit co-founder Alexis Ohanian in May 2015 (yes, there was a bit of an overlap or a very quick transition there), and by late 2016, they were engaged.
Drake, apparently, didn't take the "moving on" part very well. In his 2022 song "Middle of the Ocean," he took a direct swipe at Ohanian, calling him a "groupie." It was a weird, petty move that most fans felt was beneath him, especially since Serena was long settled into motherhood and retirement from tennis.
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Where they stand now
The relationship is clearly non-existent at this point. Serena’s appearance at the 2025 Super Bowl with Kendrick Lamar was the ultimate "Team Kendrick" statement. It suggests that whatever friendship remained after 2015 has been completely incinerated by Drake's comments about her husband and his general behavior in the years since.
What we can learn from the Drake and Serena timeline:
- Keep receipts: Drake’s music is a literal diary; if you date him, you will end up in a verse.
- Public vs. Private: They never once sat for an interview together or confirmed it while it was happening.
- The Power of Moving On: Serena’s "glow up" into a happy marriage and business empire seems to be the part that actually bothered Drake the most.
If you’re looking to understand the Kendrick vs. Drake beef deeper, looking at the women involved—like Serena and SZA—is the key. It wasn't just about rap skills; it was about how he treated the people in his life.
If you want to dive deeper into the lyrics that Drake wrote about his exes, you should look at the Views and More Life tracklists. You'll find more than a few references to "tennis matches at the crib" and "left-handed" players that confirm just how much space Serena occupied in his head.