Drake’s Star-Studded Dating History: Serena Williams, SZA and More (original) (raw)

What Drake Is Up to After Kendrick Lamar's Super Bowl Diss

While the 2025 Super Bowl was a showdown between the Kansas City Chiefs and the Philadelphia Eagles, another rivalry took center stage during Kendrick Lamar’s Halftime Show—his ongoing feud with Drake.

The “Humble.” artist appeared to throw shade at the “Hotline Bling” rapper during his 13-minute performance at Caesars Superdome in New Orleans on Feb. 9.

While performing his diss track “Not Like Us”—which received five awards, including Record of the Year, at the Grammys last week—Kendrick looked straight at the camera and rapped, “Say, Drake, I hear you like ‘em young.” The 37-year-old also wore a diamond “a” chain, and many social media users were convinced that the accessory was a nod to his “A minor” lyric—a line viewers at home could hear the crowd shouting during the show. Drake has denied the allegation of being with underage women.

But these weren’t the only moments during the Halftime Show that made viewers’ jaws drop. The performance also featured SZA and a surprise appearance from Serena Williams, who both previously dated Drake (although SZA was previously announced as a performer as she's frequently collaborated with Kendrick, including on their 2018 track “All the Stars,” and is set to tour with him this year).

However, the tennis champion and the "Kill Bill" artist aren’t the only big names to have at one time been romantically linked to the “God’s Plan” artist. Rihanna, Jennifer Lopez and Tyra Banks have, too.

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Though the public's interest in Drake’s love life has arguably been nonstop, he’s yet to find the one.

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SZA

SZA and Drake have teamed up for several songs, including "Slime You Out" and "Rich Baby Daddy." But it was on his 2020 track "Mr. Right Now" with 21 Savage and Metro Boomin that the "In My Feelings" rapper revealed he "used to date SZA back in '08."

However, SZA, who was born in 1989, later clarified "it was actually 2009" when they formed a romance, suggesting Drake took "a year of poetic rap license" and "innocently rhymed 08 w wait."

"I just didn't want anybody thinking anything underage or creepy was happening ," she tweeted. "Completely innocent. Lifetimes ago."

In fact, the "Kill Bill" artist suggested Drake gave her a heads up about the song.

"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."

Besides, SZA pointed out their romance was a long time ago.

They "were really young,” the "Snooze" singer told Rolling Stone in 2023. “It wasn’t hot and heavy or anything. It was like youth vibes. It was so childish.”

SZA appeared in the 2025 Super Bowl Halftime Show starring Kendrick Lamar, whom she's collaborated with on a number of songs, amid his beef with Drake.

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Rihanna

No need to send an SOS if you need a recap on Rihanna and Drake's history.

The singer and the rapper first sparked romance rumors in 2009 and went on to release a number of hits together, including "Work," "Take Care," "Too Good" and "What's My Name?" And while presenting Rihanna with the Vanguard Award at the 2016 MTV VMAs, Drake expressed how "she's someone I've been in love with since I was 22 years old."

But two years later, the Fenty Beauty mogul told Vogue they "don't have a friendship now, but we're not enemies either."

In 2023, Drake appeared to diss Rihanna on his track "Fear of Heights," with her fans quickly coming to her defense.

Meanwhile, the "Umbrella" artist has found love with A$AP Rocky, with whom she shares kids RZA and Riot.

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Kat Dennings

It looks like Drakeand Kat Dennings weren't meant to build an infinite playlist together. However, he did shoot his shot with the Nick and Norah’s Infinite Playlist star.

"Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight,” Drake tweeted in May 2011. “XO."

And they ended up hanging out.

"I just always had a huge crush on Kat Dennings,” Drake recalled on a 2013 episode of The Ellen DeGeneres Show, "and she was kind enough one night to oblige me and we went out to dinner."

But according to the “Hotline Bling” artist, she wasn’t exactly calling him on his cell phone afterwards.

"They don’t call me back after one date according to this," he continued. "She’s great though. She’s phenomenal."

It seems like the two had a good time, too. According to Complex, Kat revealed on a 2013 episode of Chelsea Handler’s E! show Chelsea Lately that she and Drake got sushi but that she considered it a "non-date." And while she called him a "lovely person" and "nice man," the outlet added, the 2 Broke Girls actress admitted she was "overwhelmed" by his amount of security.

Kat has been married to musician Andrew W.K. since 2023.

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Serena Williams

While Drake and Serena Williams weren’t ultimately a match, they began serving up romance rumors in 2011 with his NSFW tweet and attendance at the Canadian Open.

Over the years, the “Nonstop” rapper referenced the tennis champion on songs like 2013’s “Worst Behavior” and continued to be spotted at her events—including at her 2015 U.S. Open match and HSN runway show. In fact, Drake has credited Serena with inspiring him to finish his 2015 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.’”

Serena wed Alexis Ohanian in 2017, and Drake took a jab at him on his 2022 track “Middle of the Ocean”—calling him a “groupie.” However, the Reddit cofounder replied by simply tweeting a photo of him and daughter Olympia watching Serena on the court and writing, “The reason I stay winning is because I'm relentless about being the absolute best at whatever I do — including being the best groupie for my wife & daughter.”

Drake later revealed his 2016 song “Too Good” was also about Serena.

Meanwhile, the athlete made a joke about the Grammy winner at the 2024 ESPYs and appeared in Kendrick'sSuper Bowl Halftime Show amid his feud with Drake.

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Tyra Banks

The runway of Tyra Banks and Drake’s romance wasn’t very 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."

However, the Degrassi alum suggested his 2012 outing with the supermodel wasn’t that 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 spilled the tea, fans had a lot of questions for Tyra about their hangout.

"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, the America’s Next Top Model host sent a message to Drake in the form of a freestyle.

"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."However, it appears the two remained on good terms. Tyra even appeared in the music video for Drake’s 2016 song “Childs Play.”

She's been in a long-term relationship with Louis Bélanger-Martin, and she shares son York with ex Erik Asla.

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Jennifer Lopez

Drake and Jennifer Lopez ended 2016 by sparking dating rumors. Not only did he attend her Las Vegas residency that December, but they also appeared in a cozy photo together later that month. What’s more, the "Love Don’t Cost a Thing" singer received a diamond necklace from the “Best I Ever Had” star estimated to be worth $100,000.

And J.Lo sang Drake’s praises at the 2017 Grammys.

“I love Drake,” she told Ryan Seacrest for E! that February. “He’s so brilliant, talented, amazing.”

Jennifer also spoke about recording a song with Drake.

“We hung out. We have a great time,” she added. “He’s amazing. I have so much love for that boy.”

However, the romance rumors soon fizzled and Jennifer formed a relationship with now former fiancé Alex Rodriguez later that year.

In March 2017, Drake dropped his album More Life, which gives nods to Jennifer. On the track “Free Smoke” he raps about drunk texting her, and in “Teenage Fever," he samples her hit “If You Had My Love.”

Years after the romance rumors, Drake continued to rave about Jennifer.

"I have plenty of love for her," he told Rap Radar in 2019. "We had great times together. Yeah, we were just hanging out at one point. It was an honor to be around her. She’s a great artist, great mother."

After Jennifer—who shares twins Max and Emme with ex Marc Anthony—and Alex broke up in 2021, she wed Ben Affleck in 2022. However, she filed for divorce after two years of marriage and their split has since been finalized.

Instagram / Sophie Brussaux

Sophie Brussaux

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Julia Fox

Julia Fox was ready to cut to the chase and address those rumors that she once dated Drake.

"He's a great guy and a gentleman, and that was it," the Uncut Gems star said on a 2022 episode of her podcast Forbidden Fruits. "Nothing really happened. We were just, like, friends hanging out….Yeah, like I wouldn't say that we were dating."

However, Julia later spilled the tea on one of her best celebrity dates.

"I flew on a private jet, cuddled on the jet, landed, got some Chanel bags," she said on a 2023 episode of Watch What Happens Live. "It was just great."

While the actress initially declined to name the "A-lister" who took her on the date, host Andy Cohen later asked her if the suitor was Drake and she replied, "Maybe."

In 2022, Julia briefly dated Kanye West, who previously had a feud with Drake.

She appeared to come out in a 2024 TikTok that showed a content creator saying "I love when I see a lesbian with their boyfriend" and Julia then replying, "Hey, that was me. I was that lesbian. So sorry, boys. Won't happen again."

Instagram / Johanna Leia

Johanna Leia

In 2021, Drake sparked romance rumors with Johanna Leia, whose son is basketball player Amari Bailey.

ABC7 Eyewitness News Helicopter Reporter Chris Cristi had spotted the "God's Plan" artist on a dinner date at L.A.'s Dodger Stadium with a woman TMZ identified as the Bringing Up Ballers star.

As Chris' photos show, Drake had arranged for a table to be set up along the third base line and for there to be dinner, flowers as well as a bartender. As for how he made the luxurious date happen, a rep for the Dodgers told E! News at the time, "We can confirm that Drake made a sizable donation to the Los Angeles Dodgers Foundation in order to make his Dodger Stadium dinner date a reality."

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