The relationship between Drake and Serena Williams has long been a topic of fascination for fans, and recent events have brought their past connection back into the spotlight. During Kendrick Lamar’s highly anticipated Super Bowl Halftime Show in February 2025, the retired tennis legend made a surprise appearance as a backup dancer, sparking renewed speculation about her history with the Grammy-winning rapper. While neither Drake nor Serena has ever publicly confirmed the details of their relationship, reports and subtle hints over the years have pieced together a timeline of their romance. Here’s a closer look at when they allegedly started dating, when they broke up, and what might have gone wrong.
The timeline of Drake and Serena’s relationship remains somewhat murky, but multiple sources suggest that their romance began around 2011. At the time, both were already well-established in their respective careers, with Drake rising to fame in the music industry and Serena dominating the tennis world. Despite their busy schedules, the two reportedly developed a strong connection, with insiders hinting that their relationship was built on mutual respect and admiration. However, the timing of their lives often seemed to clash, which may have contributed to the eventual end of their relationship. According to a source who spoke to Hollywood Life in 2015, Drake and Serena had known each other for years before their romantic connection deepened, but their differing priorities and schedules kept them from taking things further. “There has always been a spark, but the timing was off,” the insider revealed.
By 2015, it appeared that Drake and Serena’s relationship had fizzled out. Although neither of them directly addressed the breakup, Drake seemed to shed light on the situation through his music. In 2016, he released the song “Too Good,” which many fans and critics interpreted as a reflection on his time with Serena. During a studio session captured in a video shared on social media, Drake admitted that the track was inspired by his relationship with the tennis star. “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.” He added that he knew Serena would hear the lyrics “loud and clear” but emphasized that the song was lighthearted, suggesting that there was no ill will between them.
The exact reason behind Drake and Serena’s breakup remains unclear, as neither of them has spoken publicly about the details. However, the lyrics of “Too Good” offer some insight into what may have gone wrong. In the song, Drake raps about a relationship where he feels taken for granted and undervalued, with his partner having “high expectations” and not fully appreciating his efforts. “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,” he sings in one verse. He also reflects on the brevity of their relationship, questioning how long they lasted and expressing regret over how things ended. While the lyrics don’t explicitly name Serena, the timing of the song’s release and Drake’s comments about its inspiration strongly suggest that she was the muse behind the track.
Drake’s reflections on the relationship, as well as the lyrics of “Too Good,” suggest that the breakup may have been amicable but unsatisfying for him. In the video from his studio session, he acknowledged that Serena was someone he knew well and cared about deeply. “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,” he said. This sentiment implies that while the relationship didn’t work out, there was still a level of mutual respect and understanding between them. It’s also worth noting that Serena has moved on to a happy marriage with Reddit co-founder Alexis Ohanian, with whom she shares two children, while Drake has continued to focus on his music and personal growth.
In the end, the story of Drake and Serena’s relationship serves as a reminder of how fleeting romance can be, even for two highly successful individuals. While their connection may have been short-lived, it clearly left an impact on both of them. For fans, the hints and clues they’ve left behind—whether through music or subtle public gestures—offer a glimpse into a relationship that, while private, was undeniably meaningful. As Drake’s music often does, “Too Good” captures the complexity of love and the challenges of balancing personal and professional ambitions, themes that resonate with listeners long after the news cycle has moved on.
