If you missed the excitement of the 2025 Super Bowl, you might be surprised to learn that Kendrick Lamar took the stage as the headliner for the Halftime Show. However, what really captured the audience’s attention was his ongoing feud with Drake. During his performance on February 9, 2025, Kendrick delivered his renowned diss track “Not Like Us,” which notably includes a lyric referencing former tennis star Serena Williams. Adding to the drama, Serena made a surprise appearance as a backup dancer, igniting speculation across social media about whether Drake and Serena had ever dated. The internet erupted with curiosity about the nature of their past relationship.

In light of this renewed interest, Hollywood Life has meticulously gathered and compiled all the known details regarding the romantic history between Serena and Drake. Their story has intrigued fans and followers alike, as they navigate the complexities of love in the public eye.

From Compton to NOLA. @SerenaWilliams @KendrickLamar #AppleMusicHalftime pic.twitter.com/mnzuP7fJ1N

— NFL (@NFL) February 10, 2025

Exploring the Romantic History of Drake and Serena Williams

Indeed, Drake and Serena have a history of dating. The talented tennis player and the renowned hip-hop artist managed to keep the intricacies of their relationship largely under wraps. Back in August 2015, a credible source informed Hollywood Life that the two had been experiencing a “slow burn” romance for a few months. This revelation added layers to the ongoing narrative surrounding their connection.

The insider provided further insight, stating, “They have known each other for years, and a chemistry has always existed between them, yet the timing was never right.” This source elaborated that Drake often teased Serena with questions like, “When are we going out?” However, it appears that Serena was skeptical about Drake’s genuine interest in her, as she never fully believed that his intentions were serious.

Timeline of Drake and Serena Williams’ Relationship

Numerous news outlets have reported that the romantic involvement between Serena and Drake likely took place between 2011 and 2015. However, the exact duration of their relationship remains somewhat ambiguous, leaving fans speculating about the details of their time together.

Reasons Behind the Breakup of Drake and Serena Williams

footage of Drake making his song with Rihanna “Too Good” off Views, he reveals to his mom that it’s about Serena Williams

she responds “I gathered that” 😂

– via 100gigs pic.twitter.com/SUMZlcU4Vl

— SOUND | Victor Baez (@itsavibe) August 7, 2024

While neither Drake nor Serena has publicly disclosed the specifics behind their breakup, it is known that the “Hotline Bling” artist confirmed in an interview that his 2016 track “Too Good” was inspired by their relationship. A revealing video clip showcasing Drake discussing the song surfaced on X in 2024, reigniting interest in their past.

In the video, Drake shared, “I get heavy on a couple joints, but this is more about me and Serena.” He continued to explain how he approaches songwriting about women he has dated, stating he aims to create songs that resonate positively with them, ensuring they appreciate his artistic expression. “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 added.

However, the lyrics in “Too Good” might not be as “lighthearted” as Drake suggested. The song conveys feelings of being taken for granted, reflecting a deeper emotional undertone that suggests struggles within their relationship.

In one of the verses, Drake poignantly raps, “I’m too good to you / I’m way too good to you,” indicating a sense of frustration and hurt. He expresses feelings of emotional investment and the pain of experiencing unreciprocated love, which many listeners can relate to.

In another verse, Drake reflects on the past, reminiscing about the relationship as he questions the length and significance of their time spent together. “Years go by too fast / I can’t keep track / How long did we last? I feel bad for asking,” he raps, showcasing a longing for clarity and closure.

He further articulates his desire to communicate his intentions, stating, “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.” This illustrates the complexity of their relationship and the emotional weight it carried for both parties.

Discovering the Identity of Serena Williams’ Husband

Serena Williams has been happily married to her husband, Alexia Ohanian, co-founder of Reddit, since November 2017. Together, they are proud parents to two beautiful daughters, named Alexis Olympia Jr. and Adira River Ohanian. Their family life is a testament to the joy and fulfillment that comes after navigating the ups and downs of relationships in the public eye.