7 Shocking Facts About Serena Williams And Drake's Explosive, On-Again, Off-Again History

The complicated, whispered-about history between tennis legend Serena Williams and hip-hop titan Drake is one of celebrity culture’s most enduring mysteries, a saga that continues to generate fresh headlines and drama even in the current date of December 10, 2025. While their rumored romance peaked nearly a decade ago, the two global superstars have repeatedly found themselves back in the spotlight, entangled in everything from cryptic song lyrics and social media shade to a fiery feud involving Serena’s husband, tech mogul Alexis Ohanian. This isn't just a story of a brief fling; it's a fascinating look at two powerhouse figures whose paths keep crossing in surprising and often explosive ways.

The latest updates in this long-running narrative are arguably the most dramatic yet, involving a major rap beef, a public diss at an awards show, and a controversial Instagram like that reignited the entire conversation. From the secret dates of 2011 to the current 2024/2025 clapbacks, the relationship between Aubrey Graham and Serena Jameka Williams remains a source of endless fascination, proving that some connections—even brief ones—leave an indelible mark on pop culture.

Serena Williams: A Brief Biography and Career Profile

Serena Jameka Williams is widely regarded as one of the greatest athletes of all time, transforming the sport of tennis alongside her sister, Venus Williams. Her life is a testament to athletic dominance, business acumen, and cultural influence.

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• Full Name: Serena Jameka Williams
• Date of Birth: September 26, 1981
• Place of Birth: Saginaw, Michigan, U.S.
• Residences: Florida, U.S.
• Nationality: American
• Spouse: Alexis Ohanian (m. 2017)
• Children: Olympia Ohanian and Adira River Ohanian
• Career Highlights: Holds 23 Grand Slam singles titles, the most by any player in the Open Era. She is a four-time Olympic gold medalist, winning three in doubles with Venus and one in singles. She has held the world No. 1 ranking in singles for 319 weeks.
• Retirement: Williams announced her "evolution" away from professional tennis in 2022.
• Business Ventures: Founder of the venture capital firm Serena Ventures and the clothing line S by Serena.
• Cultural Impact: A global icon for female empowerment, body positivity, and racial equality.

The Secret Romance: Drake and Serena’s On-Again, Off-Again Timeline (2011–2015)

The first whispers of a relationship between the Toronto rapper, Drake (Aubrey Graham), and the tennis superstar began around 2011. While neither ever officially confirmed they were a couple, their actions spoke volumes, fueling years of intense media speculation.

The Initial Spark and Public Sightings

The pair were first linked in 2011, but the rumors reached a fever pitch in 2015. Drake was frequently seen attending Serena Williams’ major tennis matches, often sitting in her box at tournaments like Wimbledon and the US Open, showing a level of support that went beyond simple friendship. This public presence at her professional events was a key indicator for fans and media alike that something serious was brewing.

The Cincinnati Kiss That Rocked the Internet

The most concrete evidence of their romance came in August 2015, when photos surfaced of the two allegedly kissing at a restaurant in Cincinnati, Ohio, shortly after Williams won the Western & Southern Open. These images served as a near-confirmation of their relationship, though they still maintained a public silence on the matter. Despite the intense scrutiny and numerous sightings, the relationship faded by the end of 2015, with Williams soon meeting her future husband, Reddit co-founder Alexis Ohanian.

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Fact: Drake’s Music is Permanently Linked to Serena Williams

Drake has a history of referencing past relationships in his music, and Serena Williams is no exception. His subtle—and sometimes not-so-subtle—lyrical nods have kept the memory of their connection alive for years, creating a permanent musical connection.

The "Too Good" Confession

Perhaps the most significant musical link came years later. In 2016, Drake released the hit song "Too Good" featuring Rihanna. While fans speculated about its inspiration, it wasn't until newly released studio footage emerged in 2024 that Drake confirmed the song was written about Serena Williams. The lyrics, which speak of a love being taken "for granted," offer a rare glimpse into Drake's perspective on their breakup.

Other Lyrical Mentions

Drake’s fascination with Williams began even earlier. In his 2013 track "Worst Behaviour," he made his first mention of the tennis star, highlighting her prowess on the court. These references show that Williams held a significant place in his life, inspiring his art long after their dating rumors subsided.

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The Modern Feud: Drake, Alexis Ohanian, and the 2024 Clapbacks

The relationship drama didn't end with their breakup; it evolved into a complex, public feud involving Serena’s husband, Alexis Ohanian, and the volatile world of celebrity social media and rap beefs. This recent tension has provided the most current and explosive news regarding the trio.

The "Groupie" Diss and Ohanian’s Response

In 2022, Drake unexpectedly reignited the feud on his song "Middle of the Ocean." In a direct line, he referred to Alexis Ohanian as a "groupie" for being a constant presence at Serena's matches. This unprovoked diss, years after Williams and Ohanian married and had their first child, Olympia Ohanian, shocked fans. Ohanian quickly responded on social media, making it clear he was unbothered and proud to support his wife, stating he was "happy" to be a "groupie" for the mother of his children. The exchange cemented the tension between the two men.

The 2024 Social Media Shade: The "Upgrade" Comment

The drama flared up again in 2024 when Drake appeared to throw shade at his former flame on Instagram. He liked a comment on a social media post that referred to rapper Sexyy Red as a "Serena Williams upgrade." This public approval of a negative comment aimed at Williams sparked immediate online backlash and renewed speculation about lingering bad blood between the two.

Serena's Epic 2024 ESPYs Tease

In a masterful move of pop culture commentary, Serena Williams delivered her own clapback during the 2024 ESPY Awards. At the height of the highly publicized rap beef between Drake and Kendrick Lamar, Williams made a surprise on-stage appearance. During the event, she teased Drake by making a reference to Kendrick Lamar, who had released the viral diss track "Not Like Us" aimed at Drake. The subtle yet powerful gesture was interpreted by fans and media as Williams taking a side in the rap war, delivering a public, lighthearted jab at her former beau and proving she is still very much in the cultural conversation, always ready for a powerful return.

From secret dates in Cincinnati to a modern-day battle of wits involving her husband and the biggest rap feud of the decade, the story of Serena Williams and Drake is a compelling narrative of fame, love, and lingering celebrity tension. The fact that their names continue to be linked in current news cycles, years after their rumored romance, underscores the enduring impact they have on each other and on the world of entertainment.