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Drake Called “Messy” After Liking Shady Comment About Ex Serena Williams Months After Super Bowl Cameo

Published on: November 20, 2025
Drake Called “Messy” After Liking Shady Comment About Ex Serena Williams Months After Super Bowl Cameo

Drake Sparks Buzz After Liking Shady Comment About Ex Serena Williams Months After Her Super Bowl Cameo

Drake is raising eyebrows once again — this time for his online activity involving ex-girlfriend Serena Williams. The Grammy-winning rapper, 39, appeared to co-sign a shady Instagram comment aimed at the tennis legend, whom he dated on and off between 2011 and 2015.

On Monday, Nov. 17, Drake posted a carousel of tennis-themed photos of himself and rapper Sexyy Red. The shoot featured rackets, court imagery, and a playful caption that read: “I said tennis lesson she said where’s the bracelet or the necklace.”

But the real drama unfolded in the comments. A user wrote “Serena Williams upgrade” accompanied by fire emojis — and Drake visibly liked the comment. Another fan quickly called him out, labeling him “messy for liking” the remark about Williams.

The interaction comes nine months after Serena Williams, 44, appeared in Kendrick Lamar’s Super Bowl halftime performance, where Lamar performed “Not Like Us,” a diss track directed at Drake. Her energetic appearance — including a crip walk inspired by her iconic 2012 Olympic celebration — immediately sparked speculation that she was subtly shading her former boyfriend.

Williams shut down those rumors in an interview with TIME in April, saying the cameo was “absolutely not” meant as a dig at Drake.
She added:
“I would never do that… It’s sad that anyone would ever think that. I respect how they could see that, but absolutely not. I have never had negative feelings toward him. We’ve known him for so many years.”

Williams, now a mother of two and retired from competitive tennis, explained that she simply enjoyed recreating a moment from her athletic past. She also admitted she’s unsure whether she regrets appearing in the Super Bowl set but emphasized that it carried no personal message for Drake.

Despite their long history — including Drake name-dropping her in the 2013 track “Worst Behavior” — the two have maintained distance in recent years. His latest Instagram activity, however, has fans questioning whether old feelings or old drama may be resurfacing.

As Drake continues to tease new music and Sexyy Red collaborations, his social media behavior is once again generating headlines — proving that when it comes to celebrity exes, the internet misses nothing.

Logan Carter

Logan Carter is a dedicated sports journalist covering major leagues and rising athletes across the United States. His sharp insights and in-depth analysis bring fans closer to the action on and off the field.