If you were scrolling through Twitter or checking sports headlines in the early 2010s, you probably remember the chaos. One minute, Drake is tweeting about making Serena Williams "sweat" during a tennis match, and the next, he’s front-row at Wimbledon looking like a permanent fixture in her player’s box. It was a weird, fascinating era of pop culture where the world's most dominant athlete and the world’s most sensitive rapper were constantly "almost" a couple.
But looking back now, the timeline is actually pretty spread out. People often ask how old was Serena Williams when she dated Drake, and the answer isn't just a single number because their "thing"—whatever you want to call it—stretched across several years and two distinct phases of their lives.
Honestly, it’s a bit of a rollercoaster.
The 2011 Rumors: Where It All Started
The first time these two sparked real dating rumors was back in 2011. At that point, Serena Williams was 29 years old (turning 30 in September of that year). Drake, meanwhile, was just 24.
The internet basically exploded when Drake was spotted at the Rogers Cup in Toronto. He wasn't just there as a fan; he was there for her. Earlier that year, he had sent a pretty flirtatious tweet to her about making her "sweat" during a match. It was the kind of public flirting that feels very 2011—unfiltered and slightly thirsty.
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They were seen playing tennis together at a Florida resort around August 2011. Imagine being 29, at the absolute peak of your powers, and having the biggest rapper in the game chasing you across the court.
Despite the sightings, they never officially said, "Yeah, we’re a couple." Serena usually brushed it off as just being friends or family. But if you ask anyone in the industry, that first spark happened when she was 29.
The 2015 "Second Act" in Cincinnati
Fast forward four years. The year is 2015, and the rumors came back with a vengeance. This is the era most people remember because of those photos. You know the ones—the blurry paparazzi shots of them looking very, very cozy at a high-end Italian restaurant in Cincinnati.
At this point, Serena Williams was 33 years old, just weeks away from her 34th birthday. Drake was 28.
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This felt different than the 2011 fling. Drake was everywhere she was. He was in her box at Wimbledon. He was at the US Open. He was even at her HSN Fashion Show in September 2015, sitting front row next to Anna Wintour. It looked like things were getting serious.
But then, just as quickly as it peaked, it fizzled. By the end of 2015, Serena had met Reddit co-founder Alexis Ohanian.
Breakdown of the Age Gap and Timing
Let's look at the numbers because the math is actually interesting. Serena is exactly five years older than Drake (she was born in 1981, he was born in 1986).
- First Linked (2011): Serena was 29/30, Drake was 24/25.
- Peak Rumors (2015): Serena was 33/34, Drake was 28/29.
It’s funny how a five-year gap feels like nothing when you’re in your 30s, but back in 2011, Drake still felt like the "new kid" on the block while Serena was already a veteran legend.
What Really Happened Between Them?
We finally got some "confirmation"—if you can call it that—years later. Drake is famous for putting his life in his lyrics, and Serena has been a recurring character in his discography for a decade.
In 2024, Drake released archival footage through his "100 Gigs" project. In one clip, he's talking to his mom, Sandi Graham, and basically admits that the song "Too Good" (his hit with Rihanna) was actually about Serena. In the song, he talks about being "too good" to someone and having his love taken for granted.
He also famously admitted in a 2019 interview that Serena helped him finish his Meek Mill diss track, "Back to Back." Apparently, they were talking about her rivalry with Maria Sharapova, and Serena told him that if he was going to go after Meek, he had to finish the job.
The Lyrics That Tell the Story
If you want to know what was going on in Drake's head, you just have to listen to the tracks:
- "Worst Behavior" (2013): "I swear I could beat Serena when she playin' with her left."
- "Nothings into Somethings" (2017): This one came out right after she got engaged. He raps about an ex getting engaged and not telling him.
- "Middle of the Ocean" (2022): This is where it got messy. He called Serena’s husband, Alexis Ohanian, a "groupie."
Alexis, for his part, handled it like a champ, tweeting that he’s the "best groupie" for his wife and daughter.
The 2025 Kendrick Lamar Twist
The story took one last wild turn in early 2025. During the Super Bowl halftime show, Kendrick Lamar performed "Not Like Us"—the ultimate Drake diss track. And who was on stage, literally Crip Walking to the song?
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Serena Williams.
She didn't have to say a word. The dance spoke for itself. It was the ultimate "I’m over it" moment from a woman who has moved on to a completely different chapter of her life as a mother, entrepreneur, and retired GOAT.
Actionable Insights: Lessons from the Serena-Drake Saga
So, what do we actually learn from this 14-year saga of "did they or didn't they"?
- Age is just a number, but maturity matters. Serena was clearly in a different headspace by the time she met Alexis Ohanian in late 2015. She went from a high-profile, "maybe" relationship with a superstar to a stable, public marriage with a tech founder.
- Privacy is a choice. Notice how Serena never actually confirmed the dating rumors in the press? She kept it vague, called him "family," and kept her private life private until she was ready to go public with her husband.
- Friendships can be complicated. Even if they "dated" at 29 and 33, they clearly maintained a friendship that influenced Drake’s biggest career moments (like the Meek Mill feud) before things eventually soured.
If you’re trying to keep track of celebrity timelines, always look at the birth years. Serena was born September 26, 1981. Drake was born October 24, 1986. That five-year gap explains a lot of the dynamic between the "GOAT" and the "Boy."
To dig deeper into the actual lyrics Drake wrote about Serena, you should check out the "100 Gigs" footage released in late 2024—it’s the closest we’ve ever gotten to a full confession about what happened when she was in her early 30s.