The 2025 Super Bowl may have featured the Kansas City Chiefs battling the Philadelphia Eagles, but Kendrick Lamar made sure another rivalry stole the spotlight — his ongoing feud with Drake.
During his 13-minute Halftime Show at Caesars Superdome in New Orleans, the “Humble.” rapper seemed to deliver subtle jabs at the “Hotline Bling” star. Lamar reignited his feud with Drake by rapping a pointed line from his Grammy-winning diss track “Not Like Us.”
Staring directly into the camera, Lamar delivered the lyric, “Say, Drake, I hear you like ‘em young,” sparking social media buzz, as reported by the E News.
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The rapper, 37, also sported a diamond “a” chain, which fans speculated referenced his controversial “A minor” lyric. Drake has previously denied allegations related to underage women.
But, this was not the only surprise delivered on the night. Appearances by SZA and Serena Williams, who have past romantic ties to Drake, was the icing on the show.
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SZA, a frequent collaborator and tour partner of Lamar, was previously announced as a performer. However, Williams’ unexpected cameo shocked viewers.
Williams and SZA may have shared the Super Bowl spotlight, but they’re not the only high-profile women linked to Drake.
The rapper’s rumored past romances include stars like Rihanna, Jennifer Lopez, and Tyra Banks. Despite ongoing public fascination with his love life, Drake has yet to settle down.
Here is a look at Drake’s star-studded dating history.
SZA
SZA and Drake have collaborated on several tracks, including “Slime You Out” and “Rich Baby Daddy.” On his 2020 song “Mr. Right Now,” Drake claimed they dated in 2008.
SZA, born in 1989, later clarified it was actually 2009, noting Drake likely used “poetic rap license” to rhyme “08” with “wait.”
“I just didn’t want anybody thinking anything underage or creepy was happening ,” she tweeted. “Completely innocent. Lifetimes ago.”
SZA revealed that Drake had informed her in advance about mentioning their past relationship in his song “Mr. Right Now.”
“We’re cool. We’ve always been cool,” she told Audacy and V103 Atlanta’s Big Tigger in 2022. “So it’s never been weird. It’s never come completely out of the blue. He let me know. Like, I didn’t know that it was a song with 21 or anything like that. Anytime he’s ever mentioned me, it’s always been positive. He’s never said anything negative about me. I’m grateful for that. And I think highly of him.”
SZA described her past relationship with Drake as a youthful, “childish” romance. She revealed that it was not serious.
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Speaking to Rolling Stone in 2023, she noted they “were really young.”
Rihanna
Rihanna and Drake’s history dates back to 2009 when romance rumors first surfaced. The duo collaborated on chart-topping hits like “Work,” “Take Care,” and “What’s My Name?”
Their bond made headlines again at the 2016 MTV VMAs when Drake, while presenting Rihanna with the Vanguard Award, confessed he’d “been in love with her since 22.”
Rihanna revealed in 2018 that she and Drake no longer maintained a friendship but weren’t enemies either. In 2023, Drake appeared to throw shade at her on his track “Fear of Heights,” prompting a swift defense from her fans.
Meanwhile, the “Umbrella” star has moved on, building a family with A$AP Rocky, with whom she shares two children, RZA and Riot.
Serena Williams
Drake and Williams sparked dating rumors in 2011, fueled by his suggestive tweet and frequent appearances at her matches, including the 2015 U.S. Open. The rapper referenced the tennis icon in songs like Worst Behavior and credited her for inspiring him to complete his Meek Mill diss track, Back to Back.
“I was with Serena at the time,” he recalled to Rap Radar in 2019, “and we had been talking a lot about her and [Maria] Sharapova going back and forth over the years.”
He added, “She’s a top competitor. So she was like, ‘You gotta finish it. Like, I’m talking about done, over. And it’s gotta be something that everyone that he’s with and him have to hear.’”
Despite their high-profile connection, the pair did not become a lasting couple.
Williams has been married to Alexis Ohanian since 2017. Ohanian became the subject of Drake’s 2022 diss track Middle of the Ocean, where he labeled Ohanian a “groupie.”
The Reddit cofounder clapped back by proudly embracing the title, sharing a photo with his daughter Olympia and praising his dedication to family.
Drake later admitted that his 2016 hit Too Good was also inspired by Williams.
Tyra Banks
Tyra Banks and Drake’s romance was brief, with their relationship not lasting long.
“It was just one date,” he explained on a 2013 episode of The Ellen DeGeneres Show. “We went to Disneyland in disguise actually, which was fun.”
He downplayed his 2012 outing with supermodel Banks, suggesting their brief relationship wasn’t serious.
“I don’t know if it was a date,” he clarified. “It was like a get-together. We’re close as well.”
After Drake revealed details about their hangout, fans were left with many questions for Banks regarding the brief encounter.
“OK, first of all, I’m watching Ellen, and I’m like, ‘I can’t believe it,'” she recalled on a 2013 episode of The Steve Havey Show. “And then my phone is hitting up and then social media—my Twitter, my Instagram: ‘Oooh, girl. You went to Disneyland? What’d you wear?’ People are going crazy, and I’m just like it’s not fair.”
So, Banks fired back with a freestyle, sending a clear message to the rapper.
“Drake rhymes with snake but no he ain’t,” she rapped. “He’s more like a lion / Going on Ellen but not lyin’. Telling the truth. What’s up dude? About that day on Disneyland / You ain’t my man—right now / But why you gotta not kiss and tell, but chill and tell / You goin’ to jail / And this is my Tyra mail.”
Drake is also reported to have dated Johanna Leia, Julia Fox, Sophie Brussaux, Kat Dennings and Jennifer Lopez.
