Drake, a global music icon, is no stranger to controversy, and his relationships with female celebrities have been at the center of much of the drama. Today, we’re ranking his worst relationships, exploring everything from public feuds to awkward, short-lived flings.

Megan Thee Stallion

Drake’s relationship with Megan Thee Stallion took a sharp turn when he seemingly took jabs at her in his 2022 album Her Loss. On the track “Circo Loco,” Drake rapped, “Lie about getting shots, but she’s still a stallion,” a line widely interpreted as a reference to Megan’s publicized shooting incident with Tory Lanez. Megan, who was shot by Lanez in 2020, responded to the line, calling out Drake for trivializing her trauma. This quickly escalated into a public spat, with fans questioning Drake’s motives and accusing him of being disrespectful toward a black woman. While Drake later claimed the lyric wasn’t about Megan, the damage was done, and the feud seemed to stem from deeper tensions, possibly rooted in past interactions and Megan’s support of Lanez’s conviction.

Ice Spice

Another artist mentioned in Her Loss was Ice Spice. On “Back Outside Boys,” Drake rapped, “She’s a 10 trying to rap, but it’s good on mute.” While this line was seen as a slight towards Ice Spice, the 24-year-old rapper took it in stride. Despite the diss, Ice Spice simply responded on social media, expressing that she was flattered to be called a “10.” Her response caught the public off guard, as it was far from the backlash many anticipated. This cooler, more diplomatic reaction earned Ice Spice goodwill with Drake’s fans, showing that sometimes a calm response can turn negative attention into positive PR.

Rihanna

Drake’s infatuation with Rihanna has been well-documented and spans over a decade. Despite many flirtations and high-profile collaborations like “What’s My Name” and “Take Care,” their relationship never blossomed into anything long-term. Drake was deeply hurt by Rihanna’s apparent disinterest in committing to him, which he referenced in his 2010 song “Fireworks.” The two were often seen together, but Rihanna consistently denied they were romantically involved, stating she preferred “hot older men.” After years of on-again, off-again flirtations, their final split in 2016 seemed to mark the end of Drake’s long-running pursuit of the Barbadian singer. Drake later addressed his heartbreak in his album For All The Dogs, referring to Rihanna and even taking shots at her new partner, ASAP Rocky.

Serena Williams

Drake’s connection with tennis legend Serena Williams began in 2011, when they were spotted at her matches and rumored to be romantically involved. Despite the public nature of their flirtation, their relationship didn’t last. In 2015, Drake made headlines with the diss track “Back to Back,” aimed at Serena’s ex, rapper Common. After their brief fling, Drake seemed to harbor some bitterness, especially after Serena moved on to marry Alexis Ohanian. Drake’s feelings resurfaced in his track “Middle of the Ocean,” where he called Serena’s husband a “groupie,” a line that sparked backlash. However, Serena’s classy response to the diss—saying she was “relentless” about being the best in her field—left Drake looking petty in comparison.

Sophie Brussaux

Sophie Brussaux, the mother of Drake’s son Adonis, had a brief relationship with him in 2017 that was initially shrouded in secrecy. Sophie, a former adult star turned artist, was thrust into the spotlight when Pusha T exposed Drake’s son in his 2018 diss track “Story of Adidon.” Drake initially denied the claim but later confirmed his paternity, sharing emotional songs about fatherhood in Scorpion. Though Drake and Sophie’s relationship ended quickly, they have managed a cordial co-parenting relationship, frequently sharing moments with their son on social media. Still, their brief connection remains one of the more awkward chapters in Drake’s romantic history.

Johanna Leia

In 2021, Drake entered a short-lived relationship with Johanna Leia, the mother of basketball prodigy Amari Bailey. The relationship seemed to revolve around Drake’s interest in Amari’s basketball career, as he was spotted courtside at Amari’s games. While their romance was never confirmed, their public outings sparked speculation that Drake was mentoring Amari to eventually gain favor with Johanna. However, their relationship fizzled by March 2022, with Johanna stating she was single and exploring her options. Drake’s pattern of short relationships continued, with many fans questioning his motives.

Millie Bobby Brown, Bella Harris, and Other Teenagers

Drake’s interactions with younger women have raised numerous eyebrows, particularly when he reached out to celebrities like Millie Bobby Brown (then 14), Bella Harris (then 18), and Tyla. While no accusations of inappropriate behavior have surfaced, the age differences and Drake’s attention to these young women were seen as concerning by some fans. The situation with Bella Harris, where Drake allegedly rented out a restaurant for her 18th birthday, further fueled the controversy. While most of these young celebrities have defended Drake as a mentor, the public perception of his behavior remains mixed.

Conclusion

From public feuds to confusing and controversial relationships, Drake’s history with female celebrities is a whirlwind of drama, tension, and speculation. While some of these relationships are simply a reflection of his high-profile lifestyle, others raise questions about his behavior toward women. Whether it’s his diss tracks, short flings, or complicated interactions with stars like Megan Thee Stallion and Rihanna, one thing is clear: Drake’s romantic and professional relationships often become part of his public persona—often to his detriment.