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Westferry Times > Entertainment > Entertainment > Drake’s star-studded relationship timeline: From Jennifer Lopez to Rihanna
Entertainment

Drake’s star-studded relationship timeline: From Jennifer Lopez to Rihanna

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By admin Published March 8, 2025
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Drake has long been a fixture in the music industry, but his romantic life has also been a source of fascination for fans. Over the years, the Canadian rapper has been linked to a string of high-profile women, including Rihanna, Jennifer Lopez, and Serena Williams. As Kendrick Lamar’s 2025 Super Bowl Halftime Show continues to dominate headlines—amidst his ongoing feud with Drake—some fans have pointed out an interesting detail: two of the event’s performers, SZA and Serena Williams, both have past connections with the rapper.

From fleeting romances to long-term relationships, here’s a look at Drake’s most notable love interests.

SZA (2009)

Drake set social media ablaze in 2021 when he claimed in his song Mr. Right Now that he had dated SZA in 2008. However, SZA later corrected the timeline, revealing it was actually 2009. The Kill Bill singer clarified their romance wasn’t serious, describing it as “youth vibes” and “childish” in a 2023 interview with Rolling Stone. Despite their past, the pair have since collaborated on two songs, Slime You Out and Rich Baby Daddy.

Ericka lee (2010-2011)

Between 2010 and 2011, Drake was romantically linked with singer Ericka Lee, whose voice can be heard on his 2011 track Marvins Room. Their relationship reportedly ended on bad terms, leading to Lee suing Drake in 2012 over songwriting credits. The lawsuit was eventually settled out of court in 2013, and Lee was credited under the name Syren Lyric Muse. Drake later referenced the situation in his song Redemption, rapping about her decision to sue him.

Serena Williams (2011-2015)

Drake and tennis legend Serena Williams were frequently rumoured to be more than friends between 2011 and 2015. The speculation reached its peak in 2015 when TMZ published a photo of the pair seemingly kissing at a restaurant. Drake was also seen supporting Williams at her fashion show and sitting courtside at her US Open matches.

In 2024, Drake’s website 100 Gigs—which features unreleased music and archived material—revealed that his 2016 hit Too Good was inspired by Williams. In a clip, he tells his mother, “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 (2009-2016)

Drake’s longest and most well-documented romance was with Rihanna. The pair were first linked in 2009 after being spotted on a date at a New York bowling alley, though they had first met in 2005 when he appeared as an extra in her Pon de Replay music video.

Their on-and-off relationship continued for years, with collaborations such as What’s My Name?, Take Care, and Work. However, by 2018, Rihanna confirmed they were no longer in touch. Speaking to Vogue, she said, “We don’t have a friendship now, but we’re not enemies either. It is what it is.”

Jennifer Lopez (2016-2017)

Rumours of a romance between Drake and Jennifer Lopez surfaced in late 2016 when he attended her Las Vegas residency. Soon after, they posted a cosy Instagram photo together, further fuelling speculation. The pair continued to praise each other publicly, but the romance fizzled out by early 2017.

Sophie Brasseux (2017 – present, co-parenting)

In October 2017, Drake welcomed his son, Adonis, with artist Sophie Brussaux. While initial reports of fatherhood were met with speculation, he confirmed the news in his 2018 album Scorpion. In his 2020 track When To Say When, Drake seemingly referred to Brussaux, rapping, “Baby mama fluke, but I love her for who she is.” Despite their past, the two now co-parent Adonis.

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Julia Fox (2020-2021)

In February 2022, actress Julia Fox revealed on her Forbidden Fruits podcast that she had once gone on a date with Drake. She described him as “a great guy and a gentleman” but insisted they were only “friends hanging out”. Later, during a 2023 appearance on Watch What Happens Live, she hinted at a lavish date with a mystery celebrity, which many speculated was Drake.

Johanna Leia (2021)

Drake was briefly linked to Johanna Leia, the mother of basketball player Amari Bailey, in 2021. The rapper reportedly mentored Bailey as he prepared to play for UCLA and even arranged a private dinner with Leia at Dodger Stadium. However, the romance seemed to be short-lived, as Leia confirmed she was single in early 2022.

Drake’s current relationship status

As of 2025, Drake appears to be single, with no confirmed romantic relationships. Despite his high-profile past, the rapper continues to keep his personal life relatively private, focusing instead on his music and ongoing feuds within the industry.

From chart-topping hits to high-profile romances, Drake’s love life has been as eventful as his career. Whether or not he finds lasting love, one thing is certain—fans will always be watching.

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