When did Drake and Rihanna date?
Rihannaand Drake had a lasting connection, but the pair lovingly dubbed “AubRih” was fraught with fighting, breakups and make-ups (and even an alleged bar fight with her ex Chris Brown). The pair first met in 2005 when Drake was working as a DJ in a Toronto restaurant where the Bajan beauty was filming her music video for one of her first hits ever, “Pon de Replay.” The pair were first reported to be linked romantically in May 2009, but it didn’t last long: In 2010, Drizzy lamented to The New York Times, “I was a pawn. You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, ‘Wow, this feels terrible.’” In 2010, the pair reunited for their collaboration “What’s My Name?” and were quite cozy in the video, leading many to speculate that their romance had rekindled. However, it once again didn’t last long, and in 2011, Drake told Ellethat Rihanna inspired his song “Fireworks.” “At the time it hurt, but she didn’t mean to. I’ll never put that on her,” he said. “I was hurt because I started to slowly realize what it was. I guess I thought it was more. That was the first girl with any fame that paid me any mind.” Later that year, however, they reunited for Drake’s song “Take Care,” and their chemistry in the accompanying music video sent tongues wagging once more about them being a couple. In June 2012, Drake and Brown were alleged to be involved in a bottle-throwing bar brawl at New York City club W.i.P., but both Brown and Drake denied any involvement (though Brown did get some nasty cuts from the melee). Later that summer, eagle-eyed MTV Video Music Awards viewers noticed Rih didn’t clap for Drake. In April 2013, Drake dissed Brown in an interview and said the “Don’t Wake Me Up” singer was insecure because “the woman he loves fell into [Drake’s] lap.” That September, he said in a sitdown with Ellen DeGeneresthat he and Rihanna “had their moment” and that he’ll always support her. In February 2014, Drake told Rolling Stonethat Rihanna was his “ultimate fantasy” but that they were just friends at that time. Though paparazzi spotted them holding hands a month later, in November 2015, Rihanna told Vanity Fairthat her last exclusive relationship was actually with Brown. By 2016, however, Drake and Rihanna were back on professionally and personally. They teamed up for her hit “Work” that February and performed the song live together at several awards shows. That August, Drake purchased a billboard in Rihanna’s honor and presented her with the Video Vanguard Award at the VMAs. Rihanna called the billboard “extra.” At the VMAs, Drake gushed, “We love the videos, which change their artistic vision from year to year. But most of all, we love the woman who hasn’t changed since day one. She’s someone…she’s someone I’ve been in love with since I was 22 years old, she’s one of my best friends in the world. All my adult life, I’ve looked up to her even though she’s younger than me. She’s a living, breathing legend in our industry.” On Rihanna’s birthday in February 2017, Drake performed all of their duets. Unfortunately, it still didn’t last, and by spring of that year, it appeared they’d called it quits yet again. In a May 2018 interview with Vogue, Rihanna revealed Drake’s penchant for PDA, including his speech for her at the VMAs, may have been the nail in the coffin of whatever relationship they’d had. “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 said, adding, “We don’t have a friendship now, but we’re not enemies either. It is what it is.” In October 2018, Drake admitted on The Shop that marrying Rihanna would have been “the fairy tale,” even admitting he would’ve liked to have kids with her someday. In 2019, Drake went on to collaborate with Brown on “No Guidance,” then again in 2020 with “Not You Too.” We see you, Aubrey.
Drake had baby mama drama with Sophie Brussaux
Drake’s other most famous romance was with visual artist and former adult film star Sophie Brussaux, mother of his son, Adonis. Rapper Pusha T revealed in his diss track “Son of Adidon” that Drake had secretly fathered a child, with lyrics including “Sophie knows better, ask your baby mother / Cleaned her up for IG, but the stench is on her / A baby’s involved, it’s deeper than rap / We talkin’ character, let me keep with the facts / You are hidin’ a child, let that boy come home / Deadbeat motherfker playin’ border patrol / Adonis is your son / And he deserves more than an Adidas press run, that’s real / Love that baby, respect that girl / Forget she’s a porn star, let her be your world.” In May 2017, TMZreported that Brussaux claimed to be pregnant with Drake’s child, but his rep snapped in a statement, “This woman has a very questionable background. She has admitted to having multiple relationships. We understand she may have problems getting into the United States. She’s one of many women claiming he got them pregnant. If it is in fact Drake’s child, which he does not believe, he would do the right thing by the child.” A DNA test proved that Adonis is, in fact, Drake’s son, and since then Drake’s both embraced his role as a father and wrestled with the situation. On his Scorpion track “March 14,” he rapped, “I had to come to terms with the fact that it’s not a maybe…She’s not my lover like Billie Jean/But the kid is mine/Sadie used to tell me all it takes is one time/And all it took was one time/St, we only met two times, two times … I’m out here on front lines/Just tryna make sure that I see him sometimes.” He spoke of fatherhood at length on The Shop, telling LeBron James (via PEOPLE), “I am a single father learning to communicate with a woman who, you know, we’ve had our moments. I do want to be able to explain to my son what happened. But I don’t have any desire for him to like, not love his mother, or I don’t ever want the world to be angry at his mother. We have found ourselves in a situation, and we are both equally responsible.” Since then, Drake and Brussaux have co-parented successfully, and he even paid a sweet tribute to her on Mother’s Day 2021. Adonis joined Drake onstage to accept the Artist of the Decade honor at the Billboard Music Awards later that May, and the little guy stole the entire show.
Drake went on a Disneyland date with Tyra Banks
Drake admitted on The Ellen DeGeneres Showthat he and Tyra Bankswent on a date to Disneyland together, but they didn’t last. Banks wasn’t too pleased that he put their once-fledgling romance on blast. The pair later teamed up for his hilarious “Child’s Play” music video.
Drake went on a single date with Kat Dennings
In May and October 2011, Drake tweeted his crush on Kat Dennings publicly. Dennings later revealed she didn’t even know he’d tweeted about her until she got hateful messages from his fans. “What happened was, and I’m glad we’re talking about this, Drake was super nice and said something on Twitter about me,” she said on Chelsea Lately (via E! News). “I didn’t realize that happened. So when I got home, I had, like, 50,000 new followers out of nowhere…they were like, ‘F**k you, Kat Dennings’ and ‘You can’t take Drake from me. He’s mine.’ And then I realized what had happened, and then we started talking and he’s super, super nice. He’s a lovely person. He’s a nice man.” Dennings revealed they got sushi together just one time on a “non-date,” adding that she was “overwhelmed” by the amount of security he had around him.
Drake dated Bad Girls Club star Catya Washington
Bad Girls Club star Catya Washington appeared in Drake’s video for “Best I Ever Had,” and the pair dated and had what she called a “regular relationship” for several months, including family dinners and leaving a toothbrush at his place. However, she claimed that he started going on trips he didn’t tell her about and getting cozy with other women, which led her to call it quits.
Did Drake and Jennifer Lopez date?
In late 2016, Drake sparked dating rumors with Jennifer Lopez. The pair looked quite cozy on Instagram, though PEOPLEreported that the duo never got serious and called it quits in early 2017, when she was first spotted with Alex Rodriguez. In 2017, Drake rapped in “Free Smoke,” “I drunk text J.Lo / Old numbers so I bounce back / Boy Wonder gotta bounce back.” In January 2018, Drake confirmed that photos of him with another woman in the Netherlands were the final nails in the coffin in his song “Diplomatic Immunity”: “2010 was when I lost my halo / 2017 I lost a J.Lo / A Rotterdam trip had me on front page, though.” That woman turned out to be Brussaux! Later, Drake told Rap Radarof Lopez, “I have plenty of love for her. We had great times together…We were just hanging out at one point. It was an honor to be around her. She’s a great artist and a great mother. [I have] nothing but positive things to say about her.”
Did Drake hook up with Kylie Jenner?
In November 2019, sources told PEOPLE that Drake was getting close romantically with longtime pal Kylie Jenner, though one source denied they were dating. In May 2020, a song leaked in which Drake called Jenner a “side piece,” and he quickly posted an Instagram Story quashing any rumors the reportedly old track may have inspired, writing, “Last thing I’d want to do is wake up having any friends of mine feeling disrespected so I just had to say that to start off the day.” For her part, Jenner reportedly laughed it off since she and Drizzy were still good pals.
Drake briefly dated Hailey Bieber
Drake was briefly linked to Hailey Bieber(then Baldwin). In 2016, a source told PEOPLE, “Drake and Hailey are dating super casually, but he is really into her. They met through mutual friends and are taking things slow.”
Drake narrowly missed his shot with Heidi Klum
So close! Heidi Klumpicked Drake out of a slew of other eligible famous bachelors (save Joaquin Phoenix) in a game of “Who’d You Rather” on The Ellen DeGeneres Show in February 2018. On her next visit to the show that September, Klum revealed that Drake actually got her number through a mutual friend and texted her…but by then she’d met Tom Kaulitz, who she went on to marry. She explained, “He was basically a week too late. I never texted him back because I found the love of my life.”
Drake wouldn’t confirm or deny his romance with Rosalyn Gold-Onwude
Drake has pretty much never walked a red carpet with anyone other than his mother, so when he attended the NBA Awards with Rosalyn Gold-Onwude on his arm in June 2017, it sent tongues wagging in a big way. He and the NBA sideline reporter never confirmed or denied any relationship beyond a friendship that began two years prior, however, and it seems they haven’t been spotted together since…but if we know Drake, we know he’s very good at keeping his private life private, so don’t rule it out entirely. Next, who doesn’t love J.Lo? Relive all of Jennifer Lopez’s famous relationships.
