Drake’s recent social media activity has reignited attention on his past relationship with Serena Williams.
On Monday, the rapper posted photos of himself and artist Sexyy Red playing tennis. “I said tennis lesson she said where’s the bracelet or the necklace,” the caption read.
While the post itself did not mention Williams, Drake’s engagement with a comment beneath it drew widespread speculation. The comment read, “Serena Williams upgrade,” which Drake liked, prompting reactions from fans who viewed the action as a subtle reference to his former partner.
Drake and Williams were in an on-and-off relationship from 2011 to 2015. Over the years, minor interactions and public statements from both parties have led to speculation about lingering tensions.
Some users criticized Drake’s Instagram engagement, with one writing, “He messy for liking this,” accompanied by a crying-laughing emoji.
This is not the first time the rapper and the tennis star have appeared in headlines together. Observers have often cited references in Drake’s music and Williams’ public appearances as potential indicators of continued rivalry or personal commentary.
History of public exchanges between Drake and Williams
In 2022, Drake referenced Serena Williams in the song “Middle of the Ocean,” from his collaborative album Her Loss with 21 Savage. The lyrics included a line targeting Williams’ husband, Alexis Ohanian:
“Sidebar, Serena, your husband a groupie / He claim we don’t got a problem but / No, boo, it is like you comin’ for sushi.”
Ohanian responded publicly on X, posting a photograph of himself and his daughter Alexis Jr. watching Williams play tennis. He captioned the post: “The reason I stay winning is because I’m relentless about being the absolute best at whatever I do – including being the best groupie for my wife & daughter.”
Speculation intensified during the 2025 Super Bowl when Williams joined Kendrick Lamar’s halftime performance.
She danced to Lamar’s song “Not Like Us,” a track interpreted by many as a diss aimed at Drake amid his ongoing dispute with Lamar. Williams later addressed the situation in an interview with TIME, stating: “I was absolutely not shading Drake.”
Despite Williams’ clarification, public discussion about the potential feud continued. Last month, Ohanian appeared on ESPN’s First Take and challenged host Stephen A. Smith after Smith suggested that Williams should reconcile with Drake following the Super Bowl appearance.
Ohanian criticized the comment, emphasizing his support for Williams and dismissing the notion that she should return to her former relationship.
Drake’s Instagram “like” has renewed speculation regarding his relationship with Williams, highlighting the sustained public interest in the former couple’s interactions.
While neither Drake nor Williams has directly commented on the recent post, social media users quickly interpreted the gesture as a possible allusion to past disputes.
The pattern of perceived references and public responses demonstrates that, despite years since their relationship ended, interactions between the parties remain subject to intense scrutiny.
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