If you were scrolling through social media during the 2025 Super Bowl, you probably saw it. Serena Williams, the undisputed greatest of all time, hitting a Crip Walk on stage while Kendrick Lamar performed "Not Like Us." It wasn’t just a dance. It was a moment. For many, it felt like a very public, very rhythmic closing of a chapter that started over a decade ago.
The history of Serena Williams Drake dating rumors is a wild ride of courtside sightings, "sushi" disses, and secret song inspirations. It’s a story that spans from 2011 to the present day, proving that even when you’re a global icon, some exes just don't know how to let go.
The Timeline: From Courtside to Cincinnati
It basically all started around 2011. People started noticing a certain Canadian rapper popping up at tennis matches. A lot of matches. Drake wasn't just there for the sport; he was there for Serena.
In those early days, they kept it low-key. Sorta. Drake would tweet things like, "@SerenaWilliams I cannot wait to put it on you and make you sweat……. during our match this weekend." Fans were losing it. But Serena, ever the professional, usually played it off. At a 2015 press conference, she even told reporters that Drake was "just like family."
The "family" narrative fell apart in August 2015.
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TMZ caught them in a private room at Sotto, an Italian restaurant in Cincinnati. They weren't just eating pasta. Photos surfaced of them making out, and witnesses said they couldn't keep their hands off each other. This was right after she won the Western & Southern Open. Drake was in the crowd for that win, too. For a brief window, it looked like they were the next power couple.
By the end of 2015, however, the vibe shifted. Serena met Reddit co-founder Alexis Ohanian. They got engaged in 2016 and married in 2017. Drake, it seems, took the "moving on" part a bit personally.
Decoding the Lyrics: Drake’s Musical Breadcrumbs
Drake is famous for "texting" his exes through his albums. Serena is no exception. Honestly, he’s been dropping her name—or references to her—for years.
- "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 one is the big one. Drake recently confirmed in his 100 Gigs archival footage that this song was specifically about Serena. He even told his mom, Sandi Graham, "This is more about me and Serena." The lyrics about being "too good" and feeling taken for granted take on a whole new meaning when you realize he was watching her move toward her future husband.
- "Nothings Into Somethings" (2017): Released right around her engagement, Drake raps, "Did I just read that you just got engaged on me?" He sounded genuinely blindsided.
The "Groupie" Comment and the Clapback
Fast forward to 2022. Drake drops "Middle of the Ocean" on the album Her Loss. Out of nowhere, he takes a shot at Serena’s husband, Alexis Ohanian.
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"Sidebar, Serena, your husband a groupie / He claim we don't got a problem but / No boo, it is like you coming for sushi."
The "sushi" line is a direct callback to those 2015 Cincinnati photos. It was petty. It was unnecessary. But Alexis Ohanian didn't miss a beat. He tweeted back: "The reason I stay winning is because I'm relentless about being the absolute best at whatever I do — including being the best groupie for my wife & daughter."
Serena’s response? A bunch of heart and smiley face emojis on her husband's post.
Why This Matters in 2026
The Serena Williams Drake dating history isn't just gossip; it’s a study in how Drake handles rejection and how Serena handles… well, life. While Drake has spent years dropping subliminal shots, Serena has built a venture capital empire, raised two daughters, and retired as a legend.
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The Kendrick Lamar Super Bowl appearance in 2025 was the ultimate "retribution," as some fans called it. By dancing to a song that explicitly says "better not speak on Serena," she signaled that she's no longer a "family" friend. She's picked a side in the rap wars, and it isn't Drake's.
What You Can Learn From the Drama
There are actually some real-world takeaways from this celebrity saga if you look past the TMZ headlines.
- Protect Your Peace: Serena almost never publicly addressed Drake's lyrics until she was ready to make a statement without saying a word. Silence is often more powerful than a Twitter rant.
- Supportive Partners Win: Alexis Ohanian's refusal to be "alpha-mailed" by Drake's lyrics showed that security in a relationship is the best defense against an ex's pettiness.
- Legacy Over Lyrics: At the end of the day, people remember Serena for her 23 Grand Slams, not who she ate sushi with in 2015. Focus on your "Slam" and the noise will fade.
If you're still curious about the specific songs where Drake mentions his exes, you should look into the 100 Gigs footage released in late 2024. It provides the most honest look we've ever gotten at how he turns his real-life heartbreak into chart-topping hits.
Next Steps for You
- Fact-check the discography: Listen to "Too Good" and "Middle of the Ocean" back-to-back to hear the tonal shift from heartbreak to bitterness.
- Follow the business moves: Check out Serena Ventures to see how the tennis star has pivoted her focus from celebrity drama to tech investment.
- Watch the Super Bowl LIX Halftime show: Look closely at the "Not Like Us" segment to see the exact moment Serena makes her stance clear.