Drake’s star-studded relationship timeline from Jennifer Lopez to Rihanna
There were many moments that made viewers’ jaws drop, but some fans might have missed that SZA and Serena Williams, who both performed live, have an interesting link to Drake – they both dated the artist.
The Kill Bill singer and the tennis champion are not the only well-known figures who have previously been romantically associated with the rapper.
Here’s everyone he has been linked with over the years.
The pair dated many moons ago
Yui Mok/PA
In his song Mr. Right Now, released in October 2021, Drake mentioned SZA by name, asserting that he and the singer had formerly dated.
“Yeah, said she wanna f— to some SZA, wait / ‘Cause I used to date SZA back in ’08,” he raps.
Later, SZA acknowledged that she and Drake had dated, but she made it clear that the rapper’s timeline wasn’t quite correct and there was no bad blood.
She tweeted at the time: “So It was actually 2009 lol … in this case a year of poetic rap license mattered. lol 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 pair worked on two songs together over the years, called Slime You Out and Rich Baby Daddy.
She commented on the relationship while talking to the Rolling Stone in 2023, clarifying that what they shared wasn’t “hot and heavy” and instead said it was “youth vibes” and “childish”.
Drake is believed to have dated Ericka Lee between 2010 and 2011, whose voice can be heard on his 2011 single, Marvins Room.
According to The Hollywood Reporter, Lee filed a lawsuit against Drake in 2012 over the song, claiming they had a professional and emotional relationship and that he was denying her co-writer payments. They also reportedly had a contentious breakup following the song’s release.
The pair settled out of court in 2013 and, while the exact details of their agreement weren’t made public, she was credited as a vocalist on the song as Syren Lyric Muse.
In a similar pattern to SZA, he references his relationship with Lee in his song Redemption.
He raps: “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.”
The pair went for sushi
Ian Gavan / Getty
The pair went on one date after Drake tweeted Kat Dennings at the time saying, “Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO”
Drake spoke about the date with Denning on the Ellen DeGeneres Show, saying: “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.”
2011-15 – Serena Williams
The pair never publicly confirmed their relationship
Mark J Terrill / AP
In 2015, TMZ shared a picture where the pair appeared to be kissing at a restaurant. The rapper also attended Williams’ fashion exhibition in the front row and cheered her on during the US Open.
Drake’s website 100 Gigs, which features unreleased music and archival material, was launched in August 2024.
According to one video clip, the rapper reveals he wrote the song Too Good from 2016 about Williams. In the video, Drake tells his mother, who isn’t seen on camera: “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 light-hearted.”
Rihanna set the record straight in 2018 that the pair weren’t seeing each other any more
Luis Alberto Rodriquez / Harper’s Bazaar UK / PA
Drake and Rihanna had an on-and-off relationship for nearly a decade, making it his most well-known romance.
They first became romantically involved in 2009, after being caught together on a date at the Lucky Strike bowling alley in New York City, despite the fact they had first met in 2005, when he appeared as an extra in her Pon de Replay music video.
But by September 2013, when Drake mentioned their relationship in the past tense in an interview on the Ellen DeGeneres Show, it appeared as though whatever spark they had shared had died. He said: “Yeah, great girl. We had our moment. Always support and have love for her and yeah.”
Drake and Rihanna were back on by 2016. In January 2016, they released her hit song Work and the music video for it a month later. By May of the same year, they were seen together at a party held after one of Rihanna’s shows in Los Angeles.
The pair collaborated on more songs and shared more PDA over the years together.
Rihanna set the record straight in 2018 that the pair were no longer an item. She told Vogue: “We don’t have a friendship now, but we’re not enemies either. It is what it is.”
Jennifer Lopez had a brief romance with the rapper
AFP via Getty Images
Rumours of a romance between Drake and Jennifer Lopez surfaced around the end of 2016. He not only went to her residency in Las Vegas that December, but they also shared a picture later that month.
The pair threw praise at each other in the following months.
But the romance rumours quickly died down and, in late 2017, Lopez started seeing Alex Rodriguez, who is now her ex-fiancé.
Drake and Sophie Brussaux have a son, Adonis, in October 2017.
Following reports he had fathered the child, the artist confirmed the rumours on his June 2018 album, Scorpion.
Drake seems to reference Brussaux in his 2020 song When To Say when he raps “Baby mama fluke, but I love her for who she is.”
Julia Fox suggested that Drake was her best celebrity date
WWD via Getty Images
“He’s a great guy and a gentleman … and that was it. Nothing really happened, we were just, like, friends hanging out. I wouldn’t say that we were dating.”
She said: “I flew on a private jet, cuddled on the jet, landed, got some Chanel bags.”
When host Andy Cohen questioned the star about if the “A-lister” who accompanied her on the date was Drake, she said, “Maybe…”
Drake reportedly dated Johanna Leia, the mother of young basketball star Amari Bailey, for a few months in 2021.
Bailey, who was scheduled to start playing basketball for UCLA in 2022, was mentored by Drake at the time.
Drake brought Leia to a private dinner inside an otherwise empty Dodger Stadium after he made a donation to the Los Angeles Dodgers Foundation, ABC 7 reported.
Drake is reportedly single now, too.
