Latest Update: Drake’s Dating History: Serena Williams, SZA, Rihanna & More

Drake’s high-profile relationships continue to capture attention as Kendrick disses him during the 2025 Super Bowl.

While the 2025 Super Bowl was all about the showdown between the Kansas City Chiefs and Philadelphia Eagles, Kendrick Lamar’s halftime performance brought a different kind of drama. Lamar, who has been feuding with Drake for months, used his time in the spotlight to throw shade at the “Hotline Bling” rapper.

During his performance of the Grammy-winning diss track “Not Like Us,” Lamar rapped, “Say, Drake, I hear you like ‘em young,” while sporting a diamond “a” chain, a potential reference to the controversial line in the song. Despite the backlash from fans, Drake has firmly denied the allegation of being involved with underage women.

However, the real drama came from Lamar’s guests: SZA and Serena Williams, both of whom have been romantically linked to Drake in the past. SZA has collaborated with Lamar on multiple tracks, including “All the Stars” from the Black Panther soundtrack, and is set to tour with him this year.

Serena Williams, the tennis legend, has also sparked romance rumors with Drake, and their connection has been referenced in Drake’s music. Their appearances at the Super Bowl added another layer to the ongoing drama between Lamar and Drake.

But Drake’s dating history doesn’t end there. The rapper’s star-studded love life has seen him linked to some of the most famous women in the entertainment industry, including Rihanna, Jennifer Lopez, and Tyra Banks.

SZA and Drake’s relationship has been an open topic for years. In 2020, Drake revealed in his song “Mr. Right Now” that he once dated SZA, though she later clarified that their romance took place in 2009, not 2008, and emphasized that it was “completely innocent”. The two artists have since remained on good terms, with SZA stating that there was no awkwardness between them. Their collaborations, including “Slime You Out” and “Rich Baby Daddy,” have only further fueled interest in their past relationship.

Drake and Rihanna’s connection has been a public affair for years. The two have been spotted together in 2016, and Drake famously declared his love for her at the MTV VMAs, calling her “someone I’ve been in love with since I was 22”. However, their relationship never fully materialized, and they eventually parted ways, though their chemistry is still present in their music, including hits like “Work” and “Take Care.” Since then, Rihanna has found happiness with A$AP Rocky, while Drake’s track “Fear of Heights” seemingly took a jab at the relationship.

In 2016, romance rumors swirled around Drake and Jennifer Lopez after they were seen cozying up together at her Las Vegas residency. Drake even gifted her a $100,000 diamond necklace, but their romance didn’t last, and Lopez later rekindled her relationship with Alex Rodriguez. In his album More Life, Drake referenced his time with Lopez in the tracks “Free Smoke” and “Teenage Fever,” which featured samples of her song “If You Had My Love.”

Though their romance was never fully confirmed, Drake and Serena Williams sparked rumors back in 2011 when Drake was spotted at her events and referenced her in his songs, including “Worst Behavior” and “Back to Back,” the latter of which was inspired by his time with Serena. The two have continued to maintain a cordial relationship, with Drake admitting that Serena inspired him to finish his Meek Mill diss track. Serena, meanwhile, married Alexis Ohanian in 2017 and the couple shares a daughter, Olympia

Sophie Brussaux, the mother of Drake’s son, Adonis, has kept a low profile in the public eye. The couple’s relationship was first confirmed by Drake in his 2018 album Scorpion, where he also addressed fatherhood. They have co-parented Adonis, who celebrated his 7th birthday in 2024, but Drake and Sophie’s romantic involvement remains a private matter.

Julia Fox briefly sparked dating rumors with Drake in 2022, and while she initially denied that they were an item, she later revealed that they had shared a luxurious private jet date during their time together. Fox, who also dated Kanye West in 2022, has spoken openly about her relationship with Drake, calling him a “great guy” and a “gentleman” but insisted that their connection was never serious.

As Drake’s dating life continues to attract attention, the rapper has been open about his focus on his career over the past few years. On a 2023 podcast, he shared, “I don’t think I can offer somebody what they’d be looking for right now, just consistency. My life, my work, is my priority.” While his love life remains a subject of fascination, it’s clear that Drake’s main focus is on his music, even as he navigates ongoing beefs, including with Kendrick Lamar, whose 2025 Super Bowl diss track has kept the feud alive.