Serena Williams and Drake Dating History

Serena Williams and Drake have been the subject of much speculation and intrigue over the years. Their relationship, though never officially confirmed, has been a topic of discussion in both the sports and music worlds. Let’s take a relaxed stroll through the timeline of Serena Williams and Drake’s dating history, shall we?

The Early Days: Sparks Fly in 2011

Back in 2011, rumors began swirling about Serena Williams and Drake. The rapper was frequently spotted at Serena’s tennis matches, cheering her on from the stands. Their chemistry was palpable, and fans couldn’t help but wonder if there was more than just friendship between the two. Drake even took to Twitter, playfully teasing Serena with a tweet that read, “@SerenaWilliams I cannot wait to put it on you and make you sweat……. during our match this weekend.” This playful banter only fueled the dating rumors further.

On-Again, Off-Again: The Rollercoaster from 2011 to 2015

Between 2011 and 2015, Serena Williams and Drake were rumored to be in an on-again, off-again relationship. They were spotted together at various events, and Drake’s presence at Serena’s matches became a common sight. In 2015, the duo was photographed getting cozy at a Cincinnati restaurant, adding more fuel to the dating rumors. Despite the public sightings, neither Serena nor Drake officially confirmed their relationship status.

Musical Musings: Drake’s Lyrics and Serena’s Influence

Drake is known for infusing his personal experiences into his music, and his relationship with Serena Williams was no exception. In his 2013 track “Worst Behavior,” he rapped, “I’m with my whole set, tennis matches at the crib. I swear I could beat Serena when she playin’ with her left.” This lyric was a clear nod to their close relationship. Later, in a behind-the-scenes video with his mother, Drake revealed that his 2016 hit “Too Good” was inspired by Serena. He explained, “It’s funny because when I make songs about women, I also make songs for them. So, I know what kind of song to make. If I’m gonna talk about them, I’ll at least do them the justice of making them a song that they like. So, I know Serena very well, and I know that she’ll hear it loud and clear, but she’ll also not hate … .”

Moving On: New Beginnings

By late 2015, it seemed that whatever romantic involvement Serena and Drake had was over. Serena began dating Reddit co-founder Alexis Ohanian, and the two announced their engagement in December … . They tied the knot in November 2017 and have since welcomed two daughters together. Drake, on the other hand, continued to reference his past relationships in his music but moved on to other romantic interests.

The Super Bowl Surprise: A Playful Nod in 2025

Fast forward to February 2025, and Serena Williams made a surprise appearance during Kendrick Lamar’s Super Bowl halftime show. She joined Lamar on stage, performing a dance during his track “Not Like Us,” a song known to be a diss track aimed at Drake. This move was seen by many as a playful jab at her former flame. Serena’s husband, Alexis Ohanian, publicly praised her performance on social media, showing his support for her playful side.

A Relationship Remembered

While Serena Williams and Drake never officially confirmed their relationship, their close bond and the moments they shared have left a lasting impression on fans. From courtside cheers to lyrical shoutouts, their connection was a blend of mutual admiration and playful interactions. Even years later, with both having moved on to different chapters in their lives, the story of Serena Williams and Drake’s dating history remains a captivating tale of two stars whose paths intertwined in the most intriguing ways.

In the end, Serena and Drake’s relationship serves as a reminder that sometimes, the most interesting stories are the ones left to the imagination, filled with playful hints and shared moments that keep fans guessing and entertained.