Drake has spent over a decade at the top of the charts, but his lyrics often suggest he’s still searching for “The One.” From secret flings and high-profile romances to the mother of his son, the Drake’s dating history is as complex as his discography. Known for his “soft-boy” persona and grand romantic gestures, the 6 God has been linked to some of the most famous women in the world.
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Drake Dating History
As we look at his journey through April 2026, here is the chronological breakdown of Drake’s most notable relationships and rumored flames.
Drake and SZA (2008–2009)
Long before they were both superstars, Drake and SZA had a brief romance. Drake famously revealed this in his 2020 track “Mr. Right Now,” rapping, “Yeah, said she wanna f*** to some SZA, wait / ‘Cause I used to date SZA back in ’08.” SZA later confirmed the timeline, clarifying it was actually 2009, but noted they have always remained on good terms.
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Ericka Lee (2010–2011)
Ericka Lee isn’t just an ex; she is the voice at the beginning of the hit song “Marvins Room.” The two had a romantic and business partnership during the early Take Care era. However, the relationship ended in a legal battle over royalties and credits for her vocal contribution to the track.
Kat Dennings (2011)
Drake’s “crush” on the 2 Broke Girls actress became a public talking point after he tweeted at her. The pair eventually went out for sushi in what Kat later described as a “non-date.” Though it didn’t evolve into a long-term romance, it remains a classic example of Drake successfully “shooting his shot” via social media.
Tyra Banks (2012)
Drake once admitted to going on a “disguised” date with the supermodel to Disneyland. To keep things low-key, Tyra reportedly wore a wig and fake glasses. While the romance didn’t last, they remained friendly enough for Tyra to star as his girlfriend in the 2016 music video for “Child’s Play.”
Drake and Serena Williams (2011–2015)
This was one of Drake’s most enduring “on-and-off” connections. He was a frequent fixture at her tennis matches, and the two were famously photographed sharing a kiss in Cincinnati in 2015. Though they eventually went their separate ways, Drake has often referenced his admiration for the GOAT in his lyrics.
Rihanna (2009–2016)
The most iconic chapter in Drake’s dating history. Their relationship spanned years of collaborations (“What’s My Name?”, “Work”, “Take Care”) and award show appearances. It peaked at the 2016 VMAs when Drake declared he had been in love with her since he was 22. Despite the cinematic romance, the two eventually grew apart, and Rihanna later stated they no longer have a friendship.
Hailey Bieber (2016)
Before she was Mrs. Bieber, Hailey Baldwin was linked to Drake during the summer of 2016. They were spotted at his Memorial Day party and later seen wearing matching “H” and “D” pendants. While sources at the time called it “casual and fun,” it never turned into a serious commitment.
Jennifer Lopez (2016–2017)
In late 2016, the internet went into a frenzy when Drake and J.Lo posted a cozy photo snuggling on a couch. They spent New Year’s Eve together and were frequently seen at each other’s events. The “relationship” was short-lived, with some fans speculating it was a savvy marketing move for a musical collaboration that never fully materialized.
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Sophie Brussaux (2017)
While not a long-term “relationship” in the traditional sense, Drake’s brief encounter with the French artist and former model changed his life forever. Their son, Adonis, was born in October 2017. Though the world didn’t find out until 2018 (via a Pusha T diss track), Drake and Sophie have since built a very healthy and supportive co-parenting relationship.
Kylie Jenner (2019)
Following Kylie’s split from Travis Scott, rumors swirled that she and Drake were spending “romantic time” together. They were reportedly “attached at the hip” at his 33rd birthday party. However, insiders later clarified that they decided to keep things as friends to avoid complicating their long-standing family ties.
Julia Fox (2020)
Before her high-profile romance with Kanye West, Julia Fox had a brief “fling” with Drake. She later confirmed on her podcast that they “hung out” in early 2020 and that he was a “great guy” and a “gentleman,” even gifting her several luxury bags during their short time together.
Johanna Leia (2021)
Drake made headlines when he rented out the entire Dodger Stadium for a private dinner date with Johanna Leia. The two were linked through the high school basketball circuit, where Drake reportedly acted as a mentor to her son, Amari Bailey. The romance lasted through the summer before they eventually drifted apart.
Where is Drake now?
Entering mid-2026, Drake remains one of Hollywood’s most eligible bachelors. While he has recently been linked to several Instagram models and was even part of the “Kim Kardashian rumor mill” earlier this year, the rapper seems focused on his “It’s All A Blur” legacy and being a father to Adonis.
CelebLoves Commentary: Drake’s dating history is proof that he wears his heart on his sleeve. Whether he’s renting out stadiums or writing entire albums about “the one that got away,” he remains the ultimate romantic of the rap world.
Which of Drake’s eras was your favorite? Are you Team Riri or do you think he’s better off single?
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