Rihanna, Drake, and His Lost Love: Serena Williams

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(ThyBlackMan.com) In the world of entertainment, where drama and relationships intertwine like vines on a trellis, the saga of Drake, Rihanna, and Serena Williams stands out as a testament to missed opportunities, complex emotions, and a flair for the dramatic. With the revelation that Drake’s 2016 hit song “Too Good,” which features none other than Rihanna, is actually about his relationship with tennis legend Serena Williams, one can’t help but dive into the layers of this juicy narrative. Why would Drake be so messy? Why let the world in on his emotions tied to Serena, a woman who is now happily married with children? And what role does Rihanna, who herself is deeply in love with A$AP Rocky and a mother to two beautiful boys, play in this tangled web?

Let’s dissect this whirlwind of emotions, choices, and why Drake, despite all his success, might have let the love of a lifetime slip through his fingers.

Drake and Serena: A Tale of What Could Have Been

To understand the magnitude of Drake’s confession, we need to rewind the clock to the mid-2010s. Serena Williams, the indomitable queen of tennis, was at the peak of her career, dominating courts worldwide with her unparalleled skill and sheer willpower. Off the court, Serena was known for her poise, grace, and a personality that radiated confidence. Enter Drake, the charming rapper with a penchant for romantic entanglements and a reputation for wearing his heart on his sleeve.

Drake and Serena were longtime friends, their relationship often described as flirtatious. The world watched with bated breath as rumors swirled about the nature of their relationship. Were they just friends, or was there something more? In 2015, those rumors reached a fever pitch when photos surfaced of the two looking cozy and affectionate, fueling speculation that they were indeed a couple.

But here’s the catch—Drake, despite being seemingly smitten with Serena, never quite treated her with the reverence she deserved. Instead of cherishing this rare connection with a woman as extraordinary as Serena, Drake continued to play the field, embodying the role of the quintessential player. He was often seen with other women, seemingly unbothered by the implications of his actions on his relationship with Serena.

Serena, ever the classy and composed figure, never publicly addressed the rumors or her relationship with Drake. But those close to her knew that she was a woman who valued loyalty, respect, and commitment—qualities that Drake, at that time, seemed unable to fully embrace.

The Messy Collaboration: Drake and Rihanna’s “Too Good”

Fast forward to 2016. Drake and Rihanna, two of the biggest names in music, collaborated on the song “Too Good,” a track that quickly climbed the charts and became an anthem of complicated love. The chemistry between Drake and Rihanna was palpable, both in the studio and on stage. Their collaborations had always been electric, and “Too Good” was no exception.

But behind the catchy beats and smooth lyrics, there was a deeper, more personal story. Recently, amid a massive drop of unreleased music and behind-the-scenes footage, Drake revealed that “Too Good” was about his relationship with Serena Williams. In a conversation with his mother, Sandi Graham, Drake candidly admitted, “This is more about me and Serena.” His mother, ever intuitive, responded that she had “gathered that,” to which Drake replied, “If I’m gonna talk about [women], 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 me for it because it’s lighthearted.”

This revelation begs the question: Why would Drake collaborate with Rihanna, another powerful woman he had a complex relationship with, on a song that was essentially about his failed relationship with Serena Williams? Was it an intentional move to stir the pot, or was Drake simply too wrapped up in his emotions to see the potential fallout?

Rihanna’s Role in the Saga

Rihanna, ever the enigmatic and fiercely independent artist, had her own history with Drake. Their relationship was a rollercoaster, filled with highs and lows, public declarations of love, and equally public breakups. By the time “Too Good” was released, Rihanna had moved on from Drake, focusing on her music, her burgeoning fashion empire, and later, her relationship with A$AP Rocky, with whom she now shares two beautiful boys.

Rihanna’s involvement in “Too Good” could be seen as a professional collaboration, but given the history between her and Drake, it’s hard not to speculate about the underlying dynamics. Did Rihanna know the song was about Serena Williams? Was she aware of the emotional baggage Drake was bringing into the studio? And if so, why did she agree to be a part of it?

Some might argue that Rihanna, ever the savvy businesswoman, saw the potential for a hit song and seized the opportunity, regardless of the personal implications. Others might suggest that Rihanna, who had her own tumultuous history with Drake, was subtly sending a message—one of indifference, or perhaps even one of power. After all, she had moved on, while Drake was still seemingly caught up in his feelings for another woman.

Why Be So Messy, Drake?

Drake’s decision to reveal that “Too Good” was about Serena Williams, years after the fact, raises several questions. For one, why bring it up now? Serena is happily married to Alexis Ohanian, co-founder of Reddit, and together they have two daughters. Serena’s life is one of fulfillment, both personally and professionally. She has retired from tennis, leaving behind a legacy that will be remembered for generations. So why would Drake choose to dredge up the past, especially when it involves a woman who has clearly moved on?

Some might argue that Drake, despite his success, has always been a man haunted by his past relationships. He’s often written songs about the women he’s loved and lost, using his music as a form of therapy. But in doing so, he sometimes crosses the line, blurring the boundaries between art and real life. By revealing the inspiration behind “Too Good,” Drake may have been seeking closure, or perhaps he was simply indulging in a moment of nostalgia.

However, it’s hard to ignore the fact that this revelation comes across as messy, even disrespectful. Serena Williams has moved on, built a beautiful life with her husband and children, and retired as one of the greatest athletes of all time. To bring her name into a conversation about an old relationship, especially in such a public way, seems unnecessary and potentially hurtful.

The Legacy of “Too Good”

“Too Good” remains one of Drake’s most popular songs, a testament to his ability to craft catchy tunes that resonate with audiences. But now, with the revelation that it’s about Serena Williams, the song takes on a new layer of meaning. It’s no longer just a catchy track—it’s a window into Drake’s complicated emotions, his missed opportunities, and his inability to fully appreciate what he had when he had it.

For Serena Williams, the revelation may be little more than a footnote in her illustrious career. She has moved on, both in her personal life and in her professional endeavors. Her legacy as a tennis legend is secure, and her role as a wife and mother brings her fulfillment beyond the tennis court.

For Rihanna, “Too Good” is just another chapter in her storied career. She has moved on from Drake, found love with A$AP Rocky, and is raising two sons in a relationship that seems grounded and real. Rihanna’s focus is on her family, her businesses, and her music, all of which continue to flourish.

A Story of Love, Loss, and Growth

In the end, the saga of Drake, Serena Williams, and Rihanna is one of love, loss, and growth. Drake, despite his success, remains a man haunted by the women he’s loved and lost. Serena Williams, ever the queen, has moved on, building a life filled with love, success, and happiness. And Rihanna, the ever-elusive superstar, continues to live life on her own terms, unapologetically and without looking back.

The revelation about “Too Good” may have stirred the pot, but in the grand scheme of things, it’s just another chapter in the lives of these three remarkable individuals. For Drake, it’s a reminder of what could have been. For Serena, it’s a distant memory of a time long past. And for Rihanna, it’s just business as usual.

As the world turns and new dramas unfold, one thing remains certain: the lives of Drake, Serena Williams, and Rihanna will continue to captivate us, whether through their music, their careers, or their personal lives. And as fans, we’ll be here, watching, listening, and speculating—because that’s what makes entertainment so endlessly fascinating.

Staff Writer; Jamar Jackson

This brother has a passion for poetry and music. One may contact him at; JJackson@ThyBlackMan.com.

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