If you were scrolling through Instagram in 2015, you probably remember the photo. It was grainy, a bit blurry, and looked like it was taken from behind a potted plant in a high-end Italian restaurant in Cincinnati. In it, Serena Williams and Drake are together, tucked into a corner booth, looking very much like a couple who didn’t want to be found.
It was the "shipping" moment heard 'round the world.
But as we look back from 2026, that era feels like a fever dream. Today, Serena is a retired legend, a mother of two, and happily married to Reddit co-founder Alexis Ohanian. Drake is... well, Drake—still releasing albums and still, apparently, holding onto a decade-old grudge. The story of Serena Williams and Drake together isn't just a "did they or didn't they" tabloid mystery. It’s a weirdly long saga involving diss tracks, tennis court side-eyes, and a very public Super Bowl dance that basically ended the conversation forever.
The Cincinnati Snaps and the Summer of 2015
Honestly, the timeline is a bit messy. Rumors about them first surfaced way back in 2011. Drake was seen at her matches, and they had some flirty Twitter exchanges that felt like peak 2011 internet. Then things went quiet. Serena was focused on being the greatest athlete on the planet, and Drake was busy becoming the biggest rapper in the world.
Then came 2015.
That summer, Drake was everywhere Serena was. He was at Wimbledon, sitting in her player box next to Anna Wintour. He was at the Rogers Cup in Toronto. He even followed her to a random tournament in Mason, Ohio—a place nobody goes unless they have a very specific reason to be there.
The Cincinnati "kissing" photos seemed to confirm everything. They looked happy. They looked close. Fans were convinced that the "6 God" and the "GOAT" were the new power couple. But the vibes shifted quickly. By the time Serena accepted her Sports Illustrated Sportsperson of the Year award in December 2015, Alexis Ohanian was the one on her arm.
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Drake was out. Alexis was in.
Why the "Too Good" Lyrics Hit Differently Now
Drake has never been one to let a breakup—or a rejection—go without a song. In 2016, he dropped "Too Good" featuring Rihanna. For years, fans speculated who it was about. In 2024, through his "100 Gigs" data dump, Drake finally confirmed what we all suspected: the song was about Serena.
In an old studio clip, he tells his mom, "This is more about me and Serena."
The lyrics paint a picture of someone feeling taken for granted. “I'm too good to you / I'm way too good to you / You take my love for granted / I just don't understand it.” It’s classic "Marvin’s Room" Drake energy. He basically admitted that while he was all-in, Serena might have just seen him as a temporary fixture.
The Lyrics That Didn't Age Well
Drake's references to Serena actually go back further than 2016. Check these out:
- 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."
- Back to Back (2015): Drake later revealed Serena actually helped inspire this Meek Mill diss. She told him he had to "finish" the feud properly.
- Middle of the Ocean (2022): This is where it got ugly. He rapped, "Sidebar, Serena, your husband a groupie."
That 2022 line was a choice. Alexis Ohanian didn't take it lying down, either. He hopped on X (Twitter) and posted, "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 and daughter."
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It was a masterclass in taking the high road while still being petty enough to win the internet for the day.
The Kendrick Lamar Factor and the Super Bowl "Crip Walk"
If you thought the drama ended with a tweet, you haven't been paying attention to the Kendrick Lamar and Drake beef. When Kendrick dropped "Not Like Us" in 2024, he explicitly told Drake, "Don't speak on Serena."
Fast forward to the February 2025 Super Bowl halftime show.
The world watched as Serena Williams herself walked onto that stage while Kendrick performed his Drake diss. She didn't just stand there; she did a crip walk—a dance she famously did at the 2012 Olympics.
Was it a direct shot? Serena told Time later that it was "absolutely not" shade and that she has no negative feelings toward Drake. She said she’s known him for years and respects him. But let’s be real: you don't jump on stage during a "certified boogeyman" performance if you’re still on great terms with the guy being dissed.
The optics were loud. It felt like the final period at the end of a very long, very complicated sentence.
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What Most People Get Wrong About Them
A lot of people think Drake and Serena were some years-long, deep romance. In reality, it seems it was a brief, intense window between 2014 and 2015 where they were "together" in the loose, celebrity sense of the word.
Serena has always been private. She doesn't do the "Instagram official" launch of a boyfriend unless it's the real deal. The fact that she never confirmed Drake but married Alexis within two years of meeting him says everything you need to know about where her heart was.
Drake, on the other hand, seems to use Serena as a benchmark for his own status. To him, being with the GOAT was a trophy. To her, he was likely just a guy she had fun with until she met her husband.
Lessons from the Serena and Drake Era
If there’s anything to learn from watching Serena Williams and Drake together (and then apart), it’s about how to handle an ex who won't stop talking.
- Silence is the ultimate power move. Serena almost never mentions Drake by name. When he disses her husband, she posts a photo of her family. When he likes shady comments about her (like he did as recently as late 2025 on an IG post with Sexyy Red), she focuses on her business, WYN Beauty.
- Support your partner publicly. Alexis Ohanian’s "best groupie" response is the blueprint for how to handle a celebrity feud. He didn't get into a rap battle; he just leaned into the love for his wife.
- Know when to move on. Drake is still making tennis references in 2026. Serena is building an empire. One of these people is stuck in 2015, and the other is winning the future.
If you're still curious about the timeline, you can look up the old 2015 Cincinnati paparazzi photos or listen to Her Loss for that "groupie" line. But honestly? The story ended at the Super Bowl. Serena danced, the world cheered, and the ball is officially out of Drake's court.
For those looking to build their own "power couple" legacy, focus on the Alexis Ohanian approach: be your partner's biggest fan and let the critics talk to the air. If you want to dive deeper into how Serena manages her post-tennis business life, checking out her recent interviews on venture capital is a great place to start.