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Drake Has Been ~in His Feelings~ a Lot: See His Past Girlfriends, Including Rihanna and Bella Hadid

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Nov 7, 2019 4:23 pm·

By Jaclyn Roth

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He’s a great catch! Drake is not only a good-looking guy, but he is also very successful in the music industry. The rapper, 33, has been nominated for a Grammy 42 times and has taken home the coveted trophy four times. It’s no wonder the ladies are attracted to the handsome hunk! The Canada native is currently dating Kylie Jenner, but who were some of his past romances with? Scroll through the gallery below to get the scoop on his love life.

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1 of 13

Rihanna

Rihanna and Drake go way back — there were rumors they went on a first date in May 2009, but later that year, she said she was “still friends” with Drake. In June 2010, Drake admitted he felt used by the pop star, 31. “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,” he told The New York Times. “I was like, ‘Wow, this feels terrible.’” Later on, the pair reunited for their song “What’s My Name.” In 2013, Drake told Ellen DeGeneres he and Rihanna “had their moment” and he will “always support and have love for her.” In 2016, they teamed up for their hit song “Work.” Drake then surprised Rihanna with a Billboard in August 2016 and delivered a heartfelt speech about the makeup mogul at the MTV VMAs. But Rihanna revealed in 2018 that she isn’t tight with Drake anymore. “We don’t have a friendship now, but we’re not enemies either. It is what it is,” she told Vogue.

2 of 13

Tyra Banks

Tyra Banks, 45, told Ellen she hung out with Drake in 2013. “We went to Disneyland in disguise actually, which was fun,” she said. “I don’t know if it was a date. It was a get-together. We’re close as well.” In fact, the model even starred in Drake’s music video for his single “Child’s Play” in 2016. In the clip, the two play a couple who are celebrating their one-year anniversary, but Tyra finds out that Drake has been cheating on her.

3 of 13

Kat Dennings

Drake revealed he was into Kat Dennings during an episode of The Ellen DeGeneres show. “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,” he said in 2013. The brunette beauty, 33, called Drake “super, super nice” and a “lovely person.”

4 of 13

Nicki Minaj

There were rumors going around for quite some time that Nicki Minaj and Drake were an item. When Drake released his debut album, Thank Me Later, he rapped about wanting to marry the hip-hop star, 36. In 2010, the duo performed on stage where Nicki and Drake apparently shared a kiss, but the Grammy winner clarified their relationship during an interview. “I saw Nicki for the first time and, like, literally fell in love,” Drake said during MTV2’s Sucker Free Countdown in 2010. “I’ve always really, actually, really had a crush on her, always really loved her, and she’s always just looked at me, as, like, her little brother.” Nicki and Drake ended up having a falling out since Drake didn’t include her or any of their Young Money family on his album. The pair made up and Nicki even gave him a lap dance in the “Anaconda” music video. “I’m so glad we found our way because I love you,” Drake told Nicki at the Billboard Awards in May 2017.

5 of 13

Ravie Loso

Drake hung out with Ravie Loso — an Instagram model — in Los Angeles in 2015. Drake also brought her to Kendall Jenner’s 20th birthday party in November 2015.

6 of 13

Hailey Baldwin

Drake and Hailey Baldwin were spotted having dinner together in Los Angeles in May 2016. Neither of them confirmed their relationship, but Drake was seen wearing Hailey’s necklace with a “H” on it. “Drake has been pursuing Hailey,” a source told Us Weekly at the time. “He has been showering her with gifts. He’s really trying hard.”

7 of 13

India Love

India Love dated Drake in October 2016, and the dad of one even dated India’s sister, Crystal Westbrooks.

8 of 13

Jennifer Lopez

Jennifer Lopez and Drake both posted the same cuddly picture of themselves on their Instagram accounts. Drake rapped about the mom of two in his song “Free Smoke” in 2017. “I drunk text J. Lo / Old number, so it bounce back,” he sang. In June 2017, a video surfaced from the 50-year old’s residency in Las Vegas after one of Drake’s song started playing. After the line, “You used to call me on your cell phone,” J. Lo said, “Huh, booty call.” Fans speculated that the pop star was throwing shade at her ex.

9 of 13

Sophie Brussaux

Drake confirmed Sophie Brussaux was the mother of his son, Adonis, on his track “March 14,” which came out in 2018. In the lyrics, Drake spoke about their strained relationship. “They said that in two weeks you’re supposed to come in town / Hopefully … Me and your mother will have come around / Instead of always cuttin’ each other down.” The pair were spotted in November 2016 and January 2017. Later on, he got candid about his relationship with the French artist. “I am a single father learning to communicate with a woman who, we’ve had our moments,” he told LeBron James on The Shop. “I do want to be able to explain to my son what happened, but I don’t have any desire for him to not love his mother. 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. Now, I’m just really excited to be a great father.” In March 2019, Drake invited Sophie to his Paris concert.

10 of 13

Rosalyn Gold-Onwude

Drake brought Rosalyn Gold-Onwude as his date to the NBA Awards in June 2017. They never confirmed or denied their relationship status, but in 2015, the sports reporter said they bonded over basketball. “The first thing was the connection because we’re both black and Jewish,” she told RESPECT magazine in 2015. “So, you know, we have that in common.”

11 of 13

Bella Hadid

On the track “Finesse,” Drake rapped about a secret relationship. “Fashion weeks is more your thing than mine,” he sang. “You stay on my mind / You and your sister too hot to handle.” Of course, fans thought the song was about Bella Hadid. However, the model, 23, shut down the rumors. “Not me!!! That’s disrespectful. WHY CAN’T PEOPLE BE FRIENDS WITHOUT ALL THE INSINUATION,” she wrote on Twitter.

12 of 13

Malaika Terry

In May 2018, Malaika Terry was spotted on a date with Drake in Toronto — shortly after Rihanna revealed she isn’t close with Drake anymore.

13 of 13

Kylie Jenner

Kylie and Drake were spotted canoodling at his birthday party in Los Angeles on October 23 but apparently, they have been “flirting for years,” a source told In Touch exclusively. “They seemed to be enjoying each other’s company,” the insider added. “They were joking around, and Kylie was laughing. There seemed to be an attraction there.” In 2013, Drake performed at Kylie’s Sweet 16 party. Prior to that, Drake partied with the Kardashian family at their family’s Christmas party in 2015. Drake also joined Kylie, 22, and her sister Kendall to celebrate New Year’s Eve in 2018.