The Untold Secret: 5 Crucial Moments In The Drake And Serena Williams Saga—From Secret Dating To The Ongoing Diss Feud

The on-again, off-again saga of rapper Drake and tennis legend Serena Williams remains one of Hollywood’s most intriguing and surprisingly long-lasting celebrity mysteries. While both have moved on—Serena is happily married to tech mogul Alexis Ohanian—the ghost of their rumored romance continues to pop up in headlines, most recently in a series of subtle social media jabs and explosive rap lyrics that have kept fans guessing as of December 10, 2025.

Far from a simple friendship, the relationship between the two superstars was reportedly an intense, passionate, and on-and-off affair that spanned several years in the early 2010s, leaving a trail of cryptic song lyrics and public appearances in its wake. The narrative has recently been reignited by new revelations and a very public, albeit indirect, feud involving Serena's husband, proving that some celebrity history is never truly over.

The Power Players: A Brief Biography of Drake and Serena Williams

The history between Drake and Serena Williams is a clash of two titans from completely different worlds: the global music industry and the elite world of professional tennis. Understanding their individual stature is key to grasping the magnitude of their rumored romance and the ensuing drama.

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• Drake (Aubrey Drake Graham)
  • Born: October 24, 1986, in Toronto, Ontario, Canada.
  • Occupation: Rapper, singer, songwriter, actor, and entrepreneur.
  • Career Highlights: One of the best-selling music artists of all time, holding numerous chart records. Known for albums like Take Care, Views, and Scorpion.
  • Nickname: Champagne Papi, Drizzy.
• Serena Williams
  • Born: September 26, 1981, in Saginaw, Michigan, U.S.
  • Occupation: Professional Tennis Player (Retired), Entrepreneur.
  • Career Highlights: Widely regarded as one of the greatest tennis players of all time. Holds 23 Grand Slam singles titles, the most by any player in the Open Era.
  • Husband: Alexis Ohanian (married 2017).
  • Children: Olympia Ohanian and Adira River Ohanian.

The Secret Timeline: 5 Key Moments in the Drake-Serena Romance

The relationship between Drake and Serena Williams was never officially confirmed by either party as a formal romance, yet multiple outlets and close sources reported that the two were an item, dating on and off for a significant period. The timeline suggests a deep connection that began long before Serena met her husband.

1. 2011: The First Rumors and Public Sightings

The earliest reports of a romantic connection between the rapper and the athlete surfaced around 2011. While they consistently maintained that they were "simply longtime friends," the public saw them together at various events, sparking the initial wave of dating speculation. This period set the stage for years of rumors and close association.

2. 2013: Drake’s First Lyrical Mention

Drake began incorporating references to Serena into his music, a pattern that would continue for years. In his 2013 track "Worst Behaviour" from the album Nothing Was the Same, he made his first mention of Williams, referencing her dominance on the court. This subtle nod confirmed their close relationship, even if the romantic nature was still under wraps.

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3. 2015: The Peak of Public Speculation

The rumors reached a fever pitch in 2015 when Drake was frequently seen supporting Serena at her tennis matches, often sitting in her players' box. Reports from the time suggested their relationship was highly "passionate and erotic" during this period. The two were photographed together on several occasions, including at her HSN Fashion Show in September 2015. However, the relationship appeared to cool down shortly after this peak, as Serena began her relationship with future husband Alexis Ohanian.

4. 2016: The Hidden Meaning in ‘Too Good’

Years after the initial rumors subsided, a massive piece of the puzzle was revealed. In 2024, newly released studio footage confirmed that Drake's 2016 hit song "Too Good," featuring Rihanna, was actually written about Serena Williams. In the song, Drake raps about his "love" for someone being taken "for granted," suggesting a deeper, more serious connection and a sense of heartbreak over their split. This 2024 revelation provided the strongest evidence yet of the intensity of their past romance.

5. 2022: The Infamous ‘Groupie’ Diss

The narrative took a dramatic turn in 2022 when Drake released the song "Middle Of The Ocean" on his album Her Loss. In a shocking and direct move, Drake took a lyrical shot at Serena’s husband, Reddit co-founder Alexis Ohanian, calling him a "groupie." This diss track escalated the tension, moving the story from a past romance to a current, public feud. Ohanian quickly responded to the diss, defending his family and status.

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The Ongoing Feud: Subtle Shots and Public Reactions in 2024–2025

Despite the years that have passed since their rumored dating ended, the tension between Drake and the Williams-Ohanian family continues to bubble up, fueled by public gestures and social media activity. The most recent events confirm that the history between them is far from settled.

Serena’s Super Bowl Dance to a Diss Track

In a move that immediately ignited social media, Serena Williams was seen dancing to Kendrick Lamar's incendiary diss track, "Not Like Us," during a Super Bowl cameo in 2025. The song was the centerpiece of Lamar’s highly publicized and lopsided rap feud victory over Drake in 2024. While the timing was conspicuous, Serena swore there was "no beef" with Drake and that her Super Bowl appearance was not intended as a diss.

Drake’s Shady Instagram Likes

Drake, however, seems less inclined to let the past go. In a recent social media stir, the rapper posted a series of tennis-themed photos with rapper Sexyy Red. He then fueled the ongoing feud by liking a comment that called his new post an "upgrade" from his ex, Serena Williams. This subtle, yet pointed, social media gesture in 2024 or 2025 (depending on the source) confirms that the tension is still very much alive and that Drake is willing to engage in the drama.

The Legacy of the Rumored Relationship

The Drake and Serena Williams story is a fascinating case study in celebrity relationships that blur the lines between friendship, romance, and public spectacle. While they never confirmed a formal relationship, the consistent lyrical references, the 2024 "Too Good" reveal, and the ongoing, indirect feud with Alexis Ohanian paint a picture of a deep, impactful connection that left a lasting impression on both their lives. For fans and media alike, the subtle shots and coded messages ensure that the "Drizzy and Serena" chapter remains one of the most compelling, unresolved storylines in pop culture history.