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.

Drake reportedly briefly dated Serena Williams in 2011, per People. The tennis star was featured during Kendrick Lamar‘s halftime performance in February 2025 at New Orleans’ Caesars Superdome. The appearance drew a major reaction from social media users amid Drake’s feud with Kendrick, which resulted in multiple diss tracks.

“Serena Williams, Drake’s ex girlfriend, crip walking to #TheyNotLikeUs is diabolical,” one person wrote on X, while another person said, “SERENA???? Kendrick had the SERENA WILLIAMS CRIP WALKING TO NOT LIKE US??? THE SAME SERENA THAT DATED DRAKE??? THIS MAN IS DIABOLICAL!!!!”

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.

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.”

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.

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.

Drake and Hailey Bieber 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 and they reportedly had some PDA moments at his Memorial Day party.
“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.” Whatever romance the pair had was short-lived, as Drake professed his feelings for Rihanna onstage at the August 2016 MTV Video Music Awards. Hailey went on to marry Justin Bieber in September 2018.

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.

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. The pair have continued to coparent their son, who lives primarily with his mother.

Drake brought Golden State Warriors sideline reporter Rosalyn Gold-Onwude as his date to the NBA Awards in June 2017. The year prior she did an interview with the rapper and he said he wanted to take her out on a date. “Yeah, it definitely caught me by surprise when I first met him,” she told Scoop B radio in 2017.
Rosalyn went on to explain that the pair bonded over basketball and developed a friendship, although she never said if they became romantic.

“He’s a big-time basketball fan,” she told Scoop B after their NBA Awards appearance. “We’ve become friends through, just his passion for the game. He’s come to a lot of games, he’s become really good friends with Steph Curry and his family.”

“So, we met through that and every time he’s around, it’s always fun, jokes, laughter. It’s a whole crew of us that’ll end up hanging out together or seeing each other at these games. So, it’s been really cool to cultivate a friendship with him,” she added. The pair were never photographed together after their red carpet appearance.

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.

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.

Kylie and Drake were spotted canoodling at his birthday party in Los Angeles on October 23, 2019, but apparently, they had been “flirting for years,” a source told In Touch exclusively at the time. “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.” The interaction occurred shortly after Kylie and boyfriend Travis Scott broke up for the first time.

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 and her sister Kendall to celebrate New Year’s Eve in 2018.

However, Drake and Kylie’s fling was short-lived. She got back together with Travis in the spring of 2021 before splitting again in early 2023.

The actress briefly dated Drake in 2020 but it was quite memorable for the Uncut Gems star. February 2022 episode of her “Forbidden Fruits” podcast, Julia gushed, “He’s a great guy and a gentleman … and that was it. Nothing really happened, we were just, like, friends hanging out,” adding, “I wouldn’t say that we were dating.”

Julia went on to reveal the best celebrity date she’d ever been on during a March 2023 appearance on Watch What Happens Live With Andy Cohen, heavily implying it was Drake.

“Being on a private jet, cuddled on the jet, landed, got some Chanel bags. It was great, yeah,” the model described the experience. When pressed by Andy who it was, Julia replied, “I can’t say. I really can’t say … obviously an A-lister.”

During the WWHL after show when Andy asked if the mystery man was Drake, she responded, “Maybe,” adding, “Shouldn’t have given me that shot.”

Drake took an interest in the model, who was the mom of young basketball phenom Amari Bailey, in 2021. They shared a romantic dinner on the field at Dodger’s Stadium and he attended several of Amari’s basketball games with Johanna, sitting court side. As of March 2022, the pair were no longer dating, as Johanna revealed she was single.