Did Drake Date Serena Williams and Have a Love Triangle with Rihanna? Here’s the Timeline

Drake’s relationship with Serena Williams has been a subject of interest for fans and media alike. But when exactly did they date, and was there ever a love triangle involving Rihanna? Here’s a breakdown of their relationships and the key moments that have fueled the speculation.

When Did Drake Date Serena Williams?

Drake and Serena Williams were rumored to have had a fling back in 2010, but it wasn’t until 2016 that their connection became more publicly acknowledged. In an exclusive video released as part of Drake’s 100 concert discount series, fans got a glimpse into his relationship with Serena. Drake was seen in the studio with his mother, Sandra Graham, playing her the hit song “Too Good,” featuring Rihanna.

In the video, Drake explained the inspiration behind his songs, stating, “When I write songs about women, I write songs for them. If I’m going to talk about them, I’ll at least make sure I write a song they’ll like.” He then mentioned Serena, saying, “I know Serena very well, and I know she’ll hear this loud and clear, but she won’t hate me for it because it’s all in good fun.”

Their relationship officially sparked rumors when Drake appeared at Serena’s tennis match against Jie Zheng at the Rogers Cup in Toronto in 2011. He made his admiration for Serena clear when he tweeted, “@SerenaWilliams, I can’t wait to show you up and make you sweat… in our match this weekend.” Despite their closeness, their official romance began in 2016, though they were frequently linked over the years.

As of 2024, Serena Williams is happily married to Alexis Ohanian, the Reddit co-founder, and they share two daughters together.

Was There a Love Triangle Between Drake, Serena Williams, and Rihanna?

The rumors about a potential love triangle between Drake, Rihanna, and Serena Williams have persisted for years, but the truth is more nuanced.

Drake and Rihanna’s relationship began back in 2005 when Drake made a cameo in her “Pon de Replay” music video. Their friendship gradually evolved into something more, and by 2009, they were caught sharing a kiss, which made headlines. The pair had an on-and-off romance throughout the years, but they also collaborated musically, notably on “What’s My Name?” in 2010 and “Take Care” in 2011.

However, the timeline of Drake’s relationships with Serena Williams and Rihanna never confirmed any love triangle involving both women at the same time. While Drake was romantically linked to both women at different points, there was no direct indication that he was dating them simultaneously. The confusion likely arose from the fact that his relationship with Serena was rumored in 2010 but didn’t officially pick up until 2016, overlapping with his on-again, off-again romance with Rihanna.

In addition, Serena Williams herself has always maintained a sense of privacy about her personal life, and despite speculation, there’s no definitive confirmation of any dramatic love triangle involving the tennis star and the pop icon.

What Did Drake Say About His Relationships?

Drake has often been open about his feelings in his music, but when it comes to his relationships, he tends to keep things subtle. In one of his interviews, he clarified that he respects both Serena Williams and Rihanna, and though there were many rumors, he never openly confirmed or denied any romantic involvement with both at the same time.

Conclusion: A Complicated Love Life

To summarize, Drake’s relationships with Serena Williams and Rihanna were both significant, but they occurred at different times. While their romantic histories intersected in the public eye, there is no confirmed love triangle between the two women. Drake’s relationship with Serena Williams started in 2016, and though they were linked romantically in earlier years, it was always separate from his long-running on-and-off relationship with Rihanna.

Drake, Serena, and Rihanna have each gone on to have successful careers and relationships, but the speculation around their love lives continues to intrigue fans and the media alike.