When Did Serena Williams & Drake Break Up? Their Split – Hollywood Life

Drake and Serena Williams‘ past connection was all over the internet thanks to Kendrick Lamar‘s February 2025 Super Bowl Halftime Show. The “Not Like Us” hitmaker brought the retired tennis player out as a backup dancer, promoting fans to speculate about her former relationship with the “God’s Plan” artist. So, when exactly did Serena and Drake date, and more importantly, when did they break up?

Below, Hollywood Life has more details about Drake and Serena’s past relationship.

When Did Serena Williams & Drake Start Dating?

The timeline of Serena and Drake’s relationship is unclear. However, multiple outlets reported that their relationship began sometime in 2011.

When Did Drake & Serena Williams Break Up?

In ‘100 gigs’ Drake shared footage of a convo with his mom, while making “Too Good, and revealing it was about Serena Williams pic.twitter.com/JmALKuxz5x

— Glock Topickz (@Glock_Topickz) August 7, 2024

Serena and Drake’s relationship fizzled out by 2015, according to multiple outlets. That year, a source told Hollywood Life that the “Hotline Bling” artist and the retired tennis pro had “been on a slow burn for a few months now.”

“They have known each other for years, and there has always been a spark, but the timing was off,” the insider added. “Drake was always saying to her, ‘When are we going out?’ Serena never seriously thought Drake was interested in her like that though.”

Though neither of them confirmed this, Drake released his song “Too Good” in 2016, which he claimed was inspired by his relationship with Serena, according to an X video from a past studio session.

Why Did Serena Williams & Drake Break Up?

In a video that emerged in 2024, Drake talked about his single “Too Good” in a studio, which he admitted was “more about [him] and Serena.”

“It’s funny because when I make songs about women, I also make songs for them,” he explained. “So, I know what kind of song to make. If I’m gonna talk about them, I’ll at least do them the justice of making them a song that they like. So, I know Serena very well, and I know that she’ll hear it loud and clear, but she’ll also not hate me for it because it’s lighthearted.”

While the reason behind their breakup remains a mystery, Drake’s “Too Good” describes an unnamed person who allegedly had “high expectations” and took advantage of him.

“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,” Drake raps in one verse. “Years go by too fast / I can’t keep track / How long did we last? I feel bad for asking. It can’t end like this … And I wanna tell you my intentions / I wanna do the things that I mention / I wanna benefit from the friendship.”