Drake's Dating History: From Rihanna to Jennifer Lopez

Mar. 15, 2025

Photo: Karwai Tang/WireImage

Drakewasn’t kidding when he called himself a certified lover boy.

The Canadian-born rapper has had several high-profile flings, including a longtime on-again-off-again relationship withRihannaand rumored romances with A-listers likeHailey Bieber, Julia Fox,Kylie JennerandJennifer Lopez.

In a November 2022deep fake interviewwithHoward Sternposted to Drake’s Instagram, Drake said he dates four or five women at a time. “I get in this habit of dating like four or five women to make one woman because I like these two things about each girl, and then I like what this girl does for a living,” he said, adding that he’s “sure he could” get married someday.

“I think that eventually, once all this is said and done for us — that addiction of work and success and forward movement is over. I feel like we’re all going to need something real. Hopefully, it’s not too late,” he said. “Hopefully, I’ll find somebody. The biggest thing is I need to be inspired.”

Drake countsSZAand Tatyana Ali among his other muses. In fact, the rapper made headlines in December 2022 when he created anecklace with 42 engagement ring diamonds, dedicated to all the times he was inspired to propose but never quite got there.

“Maybe I coulda done without, like, s—ting on people for age or disrupting somebody’s life,” he said. “The lyrics are never with ill intent, but I had somebody tell me one time, ‘You know, it’s not necessarily what you’re saying about me, it’s the fact that you said it.’ "

Drake added: “So, I’ve tried my best to stop doing that. But I like to be honest in music too so that one’s a push and pull.”

From his long-term relationships to his rumored flings, here’s a look back at Drake’s complete dating history.

SZA

SZA.Dia Dipasupil/WireImage

In October 2021, Drakename-dropped SZA in his song “Mr. Right Now,“claiming that he and the “Kill Bill” singer were previously an item.

“Yeah, said she wanna f— to some SZA, wait / ‘Cause I used to date SZA back in ‘08,” he rapped.

SZA later confirmed that she and Drake had dated, but clarified that the rapper’s timeline was a little off.

“So It was actually 2009 lol … in this case a year of poetic rap license mattered lol,“she tweeted. “I think he jus innocently rhymed 08 w wait. Anybody who really knows me and was around during this time can confirm … it’s all love all peace.”

The “Prom” singer discussed her past with Drake during a December 2022interview with Audacy.

“We’re cool, we’ve always been cool. It’s never been weird,” she said. “Anytime he’s ever mentioned me, it’s always been positive. He never said anything negative about me, and I’m grateful for that. I think really highly of him … I’m an artist now, I wasn’t then, and he’s King Drake!”

While talking toRolling Stonein October 2023, SZA shared that what she and Drake had “wasn’t hot and heavy,” instead she called it “youth vibes” and “childish.”

Ericka Lee

Drake dated a woman named Ericka Lee for a period between early 2010 and mid-2011; her voice is featured on his 2011 hit “Marvins Room.” Lee sued Drake over the track in 2012according toThe Hollywood Reporter, alleging that they had both a romantic and a business partnership and that he was withholding co-writer royalties from her from the song, and that they had an acrimonious split after the track’s release.

She was credited as a vocalist on the song as “Syren Lyric Muse,” which Drake’s legal team said was her only request at the time. Lee claimed that Drake offered her 2% of publishing royalties, then upped it to 4% to 5% and a $50,000 one-time payment and that he threatened her over the phone when she got a lawyer involved. Drake denied all the allegations.TMZ reportedthat the exes settled out of court on Feb. 2, 2013; details of whatever agreement they reached weren’t made public.

He later addressed the relationship in his song “Redemption,” rapping, “Ericka sued me and opened a business / Wonder if they wish it could’ve been different / Wonder what they’d do put in my position / I wonder, when my s**t drop, do they listen? / Wonder if they’re second guessin’ their decisions.”

Kat Dennings

Jason Merritt/Getty

Drake thirst-tweeted his way into a date withKat Dennings.

“Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO,” hetweetedat 5 a.m. ET on May 10, 2011. He latertoldEllen DeGeneres, “I just always had a huge crush on Kat Dennings, and she was kind enough one night to oblige me and we went out for dinner.”

Serena Williams

Serena Williams in 2024.Leon Bennett/Getty

Leon Bennett/Getty

Serena Williamsand Drake always maintained that they were “simply longtime friends,” despite romance rumors that swirled consistently from 2011 to 2015.

In August 2024, Drake released 100 Gigs — a website full of archival footage and unreleased songs. One particularvideo cliprevealed that the rapper wrote his 2016 track “Too Good” about Williams.

“I know Serena very well, and I know that she’ll hear it loud and clear, but not hate me for it because it’s lighthearted,” Drake said while speaking to his mom, who was off camera.

Williams, who is now married to tech entrepreneurAlexis Ohanian, made headlines in February 2025 when she made a surprise cameo duringKendrick Lamar’sSuper Bowl Halftime show. She was seen dancing to the rapper’s “Not Like Us” — a diss track aimed at Drake.

Tyra Banks

Amy Sussman/Getty

Tyra Banksand Drake went on a single date to Disneyland in 2012, herevealed onThe Ellen DeGeneres Showin 2013. When DeGeneres showed him a slideshow of women, he confirmed that he and Banks were friends and went out together once.

“I went on a date with her one time, yeah,” he told the host. “We went to Disneyland in disguise, actually, which was fun. I don’t know if it was a date. It was a get-together. We’re close as well.”

Banks appeared onThe Steve Harvey Showthat October andcalled out Drake in a playful rap, spitting, “Drake rhymes with snake but no he ain’t, 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.”

Still, the pair are good pals, with Banks co-starring in Drake’s “Child’s Play” music video in 2016.

Rihanna

Drake’s most high-profile romance was withRihanna, with whom he was in anon-again-off-again relationship for nearly 10 years. Though they met in 2005 when he was an extra in her “Pon de Replay” music video, Drake and Rihanna were first linked romantically in 2009, when there werespotted on a dateat the Lucky Strike bowling alley in New York City.

He later referenced the evening on his 2010 track “Fireworks,” rapping, “Who coulda predicted Lucky Strike would have you stuck with me? / What happened between us that night, it always seems to trouble me.” Rihanna quickly struck down romance rumors in a radio interview, however, insisting they were just friends.

In July 2011, TMZobtained photos of Drake and Rihanna getting cozy at a nightclub a few weeks prior, and in January 2012, the pair released their second collaboration, the title track from Drake’sTake Care; Rihanna also appeared with Drake in the “Take Care” music video released that April.

Over the next two years, Rihanna and Drake would each answer questions about one another in interviews. In aRolling Stoneinterviewpublished in February 2014, Drake called Rihanna “the ultimate fantasy.” RihannatoldVanity Fairin November 2015 that despite rumors of a Drake romance, her “last real, official boyfriend wasChris Brown.”

The next month, Drake and Rihanna released “Too Good,” and in July, a source told PEOPLE, “Drake has always wanted to make things work with Rihanna. They are still dating. Things get more serious when they’re in the same place.”

Samir Hussein/Redferns

Sources told PEOPLE that later that night at an afterparty, Drake “was literally shadowing her every movement and was just so affectionate and adoring the entire night.” Drake alsoposted a celebratory Instagram with Rihannato mark her big night; she later thanked him for his “touching” speech in kind and wrote, “I love you for that!”

Days later, Drake and Rihanna were spotted being affectionate both at one of his Miami concerts onstage and at a nightclub. By September, they each sported matching new tattoos of a camouflage-print plush shark that Drake had once gifted her. In October, a source told PEOPLE that Rihanna and Drake were going strong, but noted their relationship was “an open thing.”

In May 2018, Rihanna said she and Drake no longer spoke and were in a relationship with someone else. “We don’t have a friendship now, but we’re not enemies either,” shetoldVogue. “It is what it is.” She also said that Drake’s VMAs speech was awkward for her, explaining, “Waiting through that speech was probably the most uncomfortable part. I don’t like too many compliments; I don’t like to be put on blast.” She has also sincecovered up her shark tattoo.

Drake stillspoke of his romance with Rihanna warmlyin October 2018, tellingLeBron JamesinThe Shop, “As life takes shape and teaches you your own lessons, I end up in this situation where I don’t have the fairy tale, like, ‘Oh, Drake started a family with Rihanna and this is like so perfect.’ It looks so good on paper. By the way, I wanted that too at one time.”

Hailey Bieber

Frazer Harrison/Getty

In May 2016, during what was likely an off-again period with Rihanna,Hailey Bieber(then Baldwin) and Drake reportedlygot cozy at his Memorial Day party.

“They were having a lot of fun together and were very affectionate,” a source said at the time.

The pair were linked again weeks later after being spotted together at Hollywood hotspot The Nice Guy.

“Drake and Hailey aredating super casually, but he is really into her,” an insider told PEOPLE. “They met through mutual friends and are taking things slow.” He was spotted the same monthwearing her Jennifer Fisher “h” pendant necklace.

Of course, Hailey went on to marry a different Canadian crooner, tying the knot withJustin Bieberin 2018.

Jennifer Lopez

Leon Bennett/Getty Images

Jennifer Lopezand Drake sparked dating rumors in December 2016 when they worked together on a collaboration and posted the same caption-free snap of themselves cuddling on Instagram.

“They seem to really like and respect each other, but it’s early,” an insider told PEOPLE at the time. “Where it goes, we shall see. Friends of them both are hoping it becomes something, but it’s too early to say more than that.”

About a week later, a source told PEOPLE, “Jen loves the attention and she seems very happy to be spending time with him. Drake is very charming. He treats Jen with lots of respect. She seems very smitten.”

By March, Lopez was datingAlex Rodriguez.

Sophie Brussaux

Sophie Brussaux Instagram

Drake andSophie Brussauxwere not together long, but they’ll forever be linked through their son,Adonis.

In May 2018, Pusha-Trapped about Drake having a secret sonin his diss track “Son of Adidon.”

Since Drake’s paternity was proven, he and Brussaux have successfully co-parented Adonis, often sharing sweet moments with their son on social media.

Kylie Jenner

Kevin Mazur/Getty

Drake may have had a fling withKylie Jennerin 2019 during one of her off-again periods withTravis Scott(with whom she shares daughter Stormi and son Aire). A source told PEOPLE in November 2019 that Jenner and Drake took their once-platonic relationship to romance, explaining, “He and Kylie have beenspending time together recently. They’ve been friends for a long time and Drake is very close to the family.” While some insiders said the pair weredating casually, others said they weren’t dating at all.

A source later told PEOPLE, “She has been hanging out with Drake. Mostly together with other friends as well. She has known Drake for a while. Theyare not in a relationship. It mostly seems like they have chemistry, flirt and hang out. Nothing too complicated.”

Drake and Jenner had a bit of awkward history as well, as Drakepreviously feuded with Jenner’s ex Tyga.

Julia Fox

Julia Fox.Dominik Bindl/WireImage

Julia Fox was quite public in her brief romance withKanye West, but her even briefer 2020 dalliance with the “Hotline Bling” rapper flew much more under the radar.

Fox opened up about her date with Drake in a February 2022 episode of herForbidden Fruitspodcast. “He’s a great guy and a gentleman … and that was it. Nothing really happened, we were just, like, friends hanging out,” Fox said. “I wouldn’t say that we were dating.”

Fox also said that Drake and West were no longer beefing, explaining, “I feel like they’ve squashed their issues. Obviously, when I first started speaking to Ye, I told him immediately — I think on the first day, before it went any further — because I’m just an honest person.”

Johanna Leia

Vivien Killilea/Getty

In 2021, Drakedated Johanna Leia, the mom of young basketball phenom Amari Bailey, for several months, with their romance going public in July of that year. At the time, Drake acted as a mentor to Bailey, who was set to begin playing basketball for UCLA in 2022. Drake treated Leia to a private dinner at an otherwise empty Dodger Stadium after he made a donation to the Los Angeles Dodgers Foundation,ABC 7 reported. The pair appear to have fizzled out, as Leia said she was single and mingling inan interview in March 2022.

source: people.com