Drake has never been one to shy away from discussing his dating life, even if it occasionally leads to controversy. His romantic history is as colorful as his music career, filled with high-profile relationships, drama and brief flings. Let’s take a quick trip down memory lane through the notable women who have graced Drake’s heart.
SZA: Drake confirmed their past romance with a lyric in his 2020 track "Mr. Right Now," rapping about their relationship in 2008. In a playful twist, SZA later clarified that the romance actually began in 2009. She responded to the claims on X (formerly Twitter) two days later saying, “So It was actually 2009 lol ..."
Rihanna: Perhaps one of his most infamous and long-lived connections, Drake and Rihanna’s relationship was a rollercoaster stretching nearly a decade. From their first kiss in 2009 to their on-again, off-again romance, the two maintained a magnetic yet complicated relationship that kept fans guessing.
Kat Dennings: Drake went on a date with the star of "Two Broke Girls", after openly expressing his crush on her in an instance of Twitter-infused magic. The evening was a dream come true for the rapper who has always been upfront about his admiration.
Serena Williams: Their brief affair in 2011 sparked rumors that Drake’s catchy song “Too Good” was inspired by the tennis icon. Fast forward to 2025, Serena is making headlines as she was recorded dancing to Kendrick Lamar’s Drake diss track “Not Like Us” during Super Bowl LIX.
Hailey Bieber: Back in 2016, Drake and Hailey Baldwin shared a brief flirtation that insiders labeled as “super casual.” Despite the immediate sparks, the couple quickly called it quits proving some flames burn brightly but briefly.
Jennifer Lopez: Another notable encounter in 2017 saw Drake cozy up to J.Lo. Although their affair never evolved into anything serious, they certainly had fun together, mingling in the glamorous scene of Hollywood.
Sophie Brussaux: The relationship with Sophie took a came to shambles when paternity issues emerged. Drake was then forced to publicly acknowledge his son, Adonis. The rapper’s hit song "March 14" poetically addressed the complexities of fatherhood without romantic entanglements. He raps, “She’s not my lover like Billie Jean but the kid is mine...."
Julia Fox: Their 2020 connection had every element of intrigue. Julia clarified on her podcast that while they didn’t properly date, the brief spark captured public interest in a whirlwind of headlines.
Johanna Leia: Most recently, in 2022, Drake was romantically linked to Johanna Leia, the mother of basketball star Amari Bailey. Their romance surfaced when they were spotted dining together after the rapper made a donation to a Dodgers’ foundation.
In a now-deleted interview with Bobbi Althoff, the OVO head honcho candidly shared his insights into love and relationships. “I probably will not end up marrying someone famous,” he confessed, adding that famous people are often “not that intriguing.”
Drake seeks individuals who stand out from the crowd. “I like somebody that’s, like, their own. They’re not just a carbon copy.” Drake’s revealed that he had a preference for uniqueness and humor. “I like somebody with a sense of humor,” he remarked, even mentioning an interest in “cosplay” — a cheeky acknowledgement to his desire for someone with creativity and flair.
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