Entertainment

Drake’s Dating History: A Look at the Rapper’s Famous Exes

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Mar 05, 2024 / 8055 Views

Evan Walker

Aubrey Drake Graham, popularly known as Drake, isn’t just a rapper, he’s a certified heartthrob whose romantic entanglements keep the tabloids buzzing and fans swooning. Some might even say that Drake’s dating history is more complicated than the Roman Empire.

With his smooth rhymes, impeccable style and undeniable charm, Drake has become a force to reckon with in pop culture history. But beyond the beats and the bars lies a man whose dating history is as intricate and captivating as the lyrics of his songs.

After all, with an album titled Certified Lover Boy, it’s no surprise that Drake embodies the persona of a modern-day Casanova. Known for his elusive nature when it comes to matters of the heart, catching Drake in the arms of a romantic interest is akin to discovering a rare gem. Yet, despite his penchant for privacy, Drake’s relationships with nearly 20 girlfriends, most of whom are A-listers, have kept the paparazzi on their toes.

Deconstructing Drake’s dating history and his famous ex-girlfriends

From his headline-making on-again-off-again romance with Rihanna to his rumoured flings with Hailey Bieber, Julia Fox, Kylie Jenner and Jennifer Lopez, Drake’s love life has been nothing short of a whirlwind. Join us as we delve deeper into Drake’s dating history.

SZA (2009)

SZA is one of the first famous names to have made it into Drake’s dating history. Back in October 2021, he serenaded fans with the revelation that he and the Kill Bill songstress shared a chapter in his book of love. In his track Mr. Right Now, Drake dropped the bombshell, reminiscing about the dalliance with SZA in ’08 – well, almost. SZA, graciously also corrected the chronicle, revealing that their liaison actually blossomed in 2009.

Nevertheless, it’s all water under the bridge for these two, as SZA shared in an interview with Audacy in December 2022. She shared, “We’re cool, we’ve always been cool. It’s never been weird. Anytime he’s ever mentioned me, it’s always been positive. He never said anything negative about me, and I’m grateful for that. I think really highly of him … I’m an artist now, I wasn’t then, and he’s King Drake!”

Ericka Lee (2010-2011)

Next in the list of Drake’s ex-girlfriends enters Ericka Lee, the voice behind the haunting echoes of Marvins Room. Their duet on the track wasn’t just musical; it was a saga of legal battles and heartstrings pulled taut. Lee sued Drake over the song, claiming not just royalties but also a piece of his heart.

The courtroom drama unfolded like a Shakespearean tragedy, with allegations of withheld royalties and acrimonious splits. Drake denied all the allegations. TMZ later reported that the exes settled out of court on 2 February 2013; details of whatever agreement they reached weren’t made public.

Yet, amidst the legal symphony, Drake’s verse in Redemption hinted at the shadows of their past. He rapped, “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.”

Kat Dennings (May 2011)

Drake dating history — Picture Credits: Instagram/Kat Dennings

Drake dated American actress Kat Dennings sometime in 2013, all courtesy of the pop star’s late-night tweet.

Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO.

— Drizzy (@Drake) May 10, 2011

“Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO,” he tweeted at 5 am ET. Casting his net into the Twitterverse and reeling in Dennings. The two went on a date with sushi and black SUVs shadowing their every move. Dennings later regaled the thrill to comedian Chelsea Handler, the narrative punctuated by the cloak of security. A night to remember, indeed.

Tyra Banks (2012)

Drake and Tyra Banks shared a magical day at the happiest place on earth – Disneyland. Although Banks playfully teased Drake with rap verses, their bond remains unbroken. From Disneyland escapades to shared screen time in Drake’s 2016 music video Child’s Play, their friendship is woven into the fabric of stardom.

The ‘Hotline Bling’ singer revealed on The Ellen DeGeneres Show in 2013 and confirmed that he and Banks were friends and went out together once.

“I went on a date with her one time, yeah,” he told DeGeneres. “We went to Disneyland in disguise, actually, which was fun. I don’t know if it was a date. It was a get-together. We’re close as well.”

Hailey Bieber (2016)

Picture Credits: Instagram/Hailey Bieber

Another popular name in Drake’s dating history is Hailey Bieber. In the spring of 2016, amidst whispers of his past with Rihanna, Drake found himself entwined in a new romance with Hailey Bieber (Baldwin at the time) at his Memorial Day soirée. Sources whispered of their shared laughter and tender moments, hinting at a budding connection.

Their rumoured romance continued to flourish as sightings emerged at The Nice Guy restaurant. A clandestine courtship blossomed, marked by casual dates and shared trinkets, including Drake sporting Hailey’s Jennifer Fisher “h” pendant necklace.

However, Hailey’s love story took a different turn as she exchanged vows with Justin Bieber in 2018, leaving behind the echoes of her alleged fling with Drake.

Jennifer Lopez (December 2016- January 2017)

In the winter of 2016, Drake sparked dating rumours with another A-lister — Jennifer Lopez. Their alleged relationship was marked by a song collaboration, an enigmatic Instagram post and a Tiffany necklace.

Drake sampled Lopez’s If You Had My Love on his More Life track Teenage Dream. Their collaboration birthed whispers of affection, punctuated by an Instagram post capturing them cuddling. Sources murmured of mutual admiration and burgeoning affection, painting a picture of infatuation in their encounters.

The two also celebrated New Year’s Eve in 2016 together, where J. Lo sported a USD 100,000 Tiffany necklace that supposedly Drake gifted her. They allegedly dated throughout January, with Drake even meeting Lopez’s children Max and Emme, but parted ways by February.

Sophie Brussaux (2017)

Picture Credits: Instagram/Sophie Brussaux

While navigating a bunch of flings in 2016, Drake’s journey intertwined with Sophie Brussaux, a former adult film star turned painter. Their relationship might have been brief, but their bond remains eternal through their son, Adonis.

Their story began to unfold publicly in January 2017, following Drake’s split from Lopez. Speculation swirled as Brussaux reportedly claimed she carried Drake’s child. Initially, Drake denied the assertions, his representative stating to PEOPLE, “If it’s in fact Drake’s child, which he does not believe it is, he will do right by the child. She’s just another woman in a long line of women claiming he got them pregnant.”

In May 2018, Pusha-T’s diss track Son of Adidon thrust Drake’s paternity into the spotlight. Despite initial denials, TMZ reported Drake’s financial support for Brussaux before Adonis’s birth on 11 October 2017. A subsequent paternity test in March 2018 confirmed Drake as the father. Drake candidly addressed the situation, referencing the test and his mother, Sandi Graham, in the introspective track March 14 from his album Scorpion, rapping, “She’s not my lover like Billie Jean but the kid is mine/Sandi used to tell me all it takes is one time, and it took was one time/S—, we only met two times, two times.”

Since the paternity revelation, Drake and Brussaux have been co-parenting Adonis, sharing tender moments on social media.

Rosalyn Gold-Onwude (2017)

Picture Credits: Instagram/Rosalyn Gold-Onwude

Drake ignited dating rumours with NBA sports broadcaster Rosalyn Gold-Onwude around the time of the 2017 NBA Finals. His choice of companion, diverging from the norm of appearing with his mother, set eyebrows arching in surprise.

In a playful nod to their camaraderie, Drake had previously teased their connection back in December 2015, sharing a candid picture on Instagram. Yet, the intriguing status of their relationship lingered in uncertainty. Speculation swirled, but confirmation remained elusive. The whispers intensified when Rosalyn, amidst Drake’s infamous feud with Pusha T, reportedly engaged with a tweet aligning with Pusha T’s sentiments, adding another layer of intrigue to their story.

Jorja Smith (2017)

Drake’s reported relationship with British singer Jorja Smith in 2017 had fans buzzing with speculation and intrigue. The rapper didn’t shy away from flaunting his connection with the Blue Lights songstress, taking to Instagram to share snapshots of their time together. Their chemistry wasn’t confined to just social media; Smith joined Drake as the opening act on the Birmingham leg of his Boy Meets World Tour, further fuelling speculation about the nature of their relationship.

Their romance even extended to Smith’s hometown of Walsall, where they were spotted together, prompting insiders to suggest that what they shared was more than just a fling. In fact, in a grand gesture, Drake had inked the number ’11’ on his skin as a tribute to Smith’s birthday.

However, as with Drake’s previous relationships, things took a turn, and the couple parted ways. Drake’s song ‘March 14th’ from his album Scorpion hinted at the evolution of the tattoo’s significance, suggesting that it now honoured his son Adonis’ birthday, signifying the end of his relationship with Jorja Smith.

Rihanna (2009-2018)

Drake’s most iconic romance was with pop sensation Rihanna, with whom he was in an on-again-off-again relationship for over a decade. Their lyrical dating started in 2009 amidst the neon-lit alleys of NYC’s Lucky Strike bowling alley, immortalised in Drake’s 2010 track ‘Fireworks.’ Despite Drake’s obvious hints, Rihanna brushed off rumours, asserting their relationship was platonic.

Perhaps bored of chasing, in 2010, Drake dubbed himself as a pawn in Rihanna’s game of love. He said in an interview with The New York Times, “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. I was like, wow, this feels terrible.” Later that year, however, they apparently reconciled and were amicable enough to collaborate on her hit ‘What’s My Name’ and performed together at the 2011 Grammys.

The intrigue persisted, with TMZ capturing cosy moments in nightclubs, and their chemistry pulsating in the ‘Take Care’ music video. By 2013, Drake reminisced on The Ellen DeGeneres Show, acknowledging their past with fondness. “Yeah, great girl. We had our moment. Always support and have love for her and yeah.” Throughout the years, interviews crackled with hints of longing; Drake lauded Rihanna as his ultimate fantasy, while Rihanna recovered from her past with Chris Brown.

Their romantic overture resumed in 2016, marked by the release of the hit ‘Work’. Drake’s public gestures, from onstage proclamations to billboards, underscored his devotion. Their affection blossomed, evident in shared tattoos and PDAs.

In August 2016, Drake made their romance more public in several ways. He brought Rihanna onstage during OVO Fest and quipped, “You showed up two nights in a row for my city. You might have to go half on a baby.”

Later that month, before the 2016 MTV Video Music Awards, he bought a billboard in LA that read, “Congratulations to Rihanna from Drake and Everyone at Ovo.” Rihanna posted a photo of the billboard on Instagram, captioning it, “When he extra ❤🏆!!!”

On 28 August 2016, Drake presented the ‘Diamond’ singer the MTV Michael Jackson Video Vanguard Award, telling the crowd, “She’s someone I’ve been in love with since I was 22 years old. She’s one of my best friends in the world. She’s a living breathing legend in our industry.”

Yet, like a fading crescendo, their romance waned. Rihanna’s birthday performance in 2017 marked their swan song, as she drifted into new chapters, her matching shark tattoo buried beneath layers of memory.

In May 2018, Rihanna said she and Drake were no longer in touch. “We don’t have a friendship now, but we’re not enemies either,” she told Vogue, adding, “It is what it is. Waiting through that speech (VMAs) was probably the most uncomfortable part. I don’t like too many compliments; I don’t like to be put on blast.” Rihanna’s interview with Vogue marked an end to this whirlwind chapter in Drake’s dating history.

Bella Hadid (2017-2018)

The next name to make it to the starry list of Drake’s ex-girlfriends is that of supermodel Bella Hadid. In October 2017, whispers emerged, suggesting a secret liaison spanning four months, evolving from casual dalliance to a purportedly serious affair.

Gossips spun tales of lavish celebrations, with Drake allegedly orchestrating a soirée to commemorate Hadid’s 21st birthday. Yet, their entanglement unfurled against a backdrop of complexity — Hadid’s former flame at the time was Abel ‘The Weeknd’ Tesfaye, a close associate and frequent collaborator of Drake.

Tensions simmered as dynamics shifted in the celebrity circles. The purported romance between Drake and Hadid cast shadows upon the friendship shared with The Weeknd.

Ultimately, Hadid started seeing The Weeknd again, leading to a renewed courtship that endured until their final parting in 2019.

Bella Harris (September 2018)

Next, another Bella entered Drake’s life, this time model Bella Harris. The two allegedly dated briefly in September 2018, orchestrating an exclusive rendezvous that reportedly commandeered an entire restaurant in Washington.

Harris, the daughter of renowned music producer Jimmy Jam, brought an air of intrigue to the liaison. Yet, whispers of their romance stirred eyebrows, as Bella, merely 18 at the time, stood in stark contrast to Drake, who was 31.

Amidst the swirling rumours, Harris took to Instagram to dispel the conjecture, firmly denying the alleged affair. “Coming off an amazing New York fashion week, I feel I need to set the record straight,” she affirmed, “I did not dine in DC recently. I was happily working & dining in NYC everyday.”

Serena Williams (rumoured)

Between 2011 and 2018, Drake’s presence court-side at Serena Williams‘ Tennis matches stirred speculations of a potential romance. While the duo never officially confirmed their relationship, public sightings and moments captured them sharing affection added to the speculations.

Drake’s cryptic tweets and lyrical references further fuelled speculation. In one tweet, he alluded to “putting it on her and making her sweat” during a Tennis Game, while his 2013 track ‘Worst Behaviour’ featured lines seemingly nodding to the Tennis champion. He rapped, “I’m with my whole set/Tennis matches at the crib/ I swear I could beat Serena when she playin’ with her left.”

Despite the intrigue surrounding their alleged romance, both Drake and Serena maintained the silence of ambiguity around their relationship, leaving fans to speculate about the nature of their connection.

Nicki Minaj (rumoured)

Drake and Nicki Minaj’s bond traces back to their shared tenure on Lil Wayne’s Young Money label, a camaraderie that has lasted more than a decade.

Since Drake’s declaration of wanting to marry Nicki Minaj on his debut album Take Care in 2010, buzz of a potential romance between the two has lingered in the air. One notable instance was in Nicki’s ‘Anaconda’ music video, where she bestowed Drizzy with a playful lap dance, igniting further speculation about the depth of their connection.

Moreover, Drake and Nicki teased their followers with a faux-marriage stunt, playfully hoodwinking fans into believing they had tied the knot.

While Minaj has remained steadfast in categorising Drake as a brotherly figure, their playful antics and shared history continue to fuel speculations about the true nature of their bond.

Kylie Jenner (2019)

In late 2019, whispers emerged suggesting that Kylie Jenner, fresh from her split with Travis Scott, may have crossed paths romantically with Drake. Sources hinted at ‘mutual feelings’ between them. However, subsequent reports indicated a cooling off, with insiders suggesting Kylie was deterred by Drake’s reputation as a notorious womaniser, affirming, “She’s smarter than that.”

Drake’s association with the Kardashian-Jenners, spanning years of friendship and collaborations, added layers of intrigue to the alleged affair. Notably, he graced Kylie’s 16th birthday celebration with a memorable performance.

In May 2020, a song surfaced during a livestream featuring Drake referring to Kylie as a ‘side-piece,’ prompting swift clarification from the rapper on Instagram. He attributed the mishap to an old leak, apologising for any unintended offence caused to his friends.

Addressing the incident, Drake expressed his commitment to preserving the respect of those close to him, ensuring they did not feel slighted by the lyrics. Kylie, reportedly, took the matter in stride, laughing off the song’s content.

Julia Fox (2020)

While Julia Fox’s whirlwind romance with Kanye West made headlines, her even more fleeting romance with Drake remained largely under the radar.

In a revealing episode of her Forbidden Fruits podcast in February 2022, Fox shared insights into her encounter with Drake. Describing him as a “great guy and a gentleman,” she clarified that their interaction was purely platonic. “Nothing really happened, we were just, like, friends hanging out,” Fox disclosed, firmly dispelling any notions of romantic entanglement. “I wouldn’t say that we were dating,” she affirmed.

Moreover, Fox shed light on the evolving dynamics between Drake and West, suggesting that their animosity had subsided. She candidly informed West about her conversation with Drake early on, underscoring her commitment to honesty in relationships.

In a subsequent interview on Watch What Happens Live With Andy Cohen in January 2023, Fox let slip that Drake was, in fact, her most memorable celebrity date. Despite initially keeping his identity under wraps, she recounted the allure of being whisked away on a private jet, indulging in intimate moments, and even receiving Chanel bags as tokens of affection, bringing to the fore another bougie escapade in Drake’s dating history.

Naomi Sharon (2020)

In the ballad of Certified Lover Boy, a new verse emerged – that of Naomi Sharon. The recording sessions of Drake’s album intertwined with whispers of romance, leaving hearts aflutter and tongues wagging. Rumours swirled that Drake may have played a part in the breakup of Sharon’s relationship with her now ex-fiancé Jamie Sun.

Yet, amidst the whispers, both Drake and Sharon maintain a stoic silence, leaving the world to speculate on the nature of their relationship.

Johanna Leia (2021)

In July 2021, Drake was spotted on an intimate date with model and reality TV star Johanna Leia at an empty Dodger Stadium in Los Angeles. What seemed like a spontaneous outing unveiled a mysterious romance that had been brewing for months, as reported by TMZ.

It’s believed that Drake and Leia crossed paths through high school basketball, where her son, Amari Bailey, shines as a future star. The rapper reportedly extended mentorship to Amari, sharing insights on finance, fame and navigating the challenges of stardom.

Their bond extended beyond basketball conversations, with Drake reportedly spending quality time with Amari individually and together with Leia at his residence. Their connection hinted at a fonder rapport beyond casual dating.

However, just three months later, reports surfaced of the pair parting ways, marking the end of their alleged relationship.

Camila Cabello (December 2023)

Rumours have been swirling about a potential romance between the former Fifth Harmony member and the charismatic Drake. The buzz ignited when the duo was spotted engaging in lively conversation during a vacation in Turks and Caicos in December 2023.

Several clips capturing Cabello and the ‘You Broke My Heart’ rapper in animated discussion surfaced, circulating widely as they shared laughter aboard a boat near the laid-back Noah’s Ark Beach Club. Additional sightings captured the pair cruising along the ocean waters on separate jet skis, adding fuel to the speculation.

Despite the flurry of sightings and viral clips, neither artist has divulged details about their time together on social media platforms. Furthermore, neither party confirmed nor denied the status of their relationship. Both Camila and Drake boast relationship histories, adding layers of intrigue to the speculations surrounding their alleged connection.

Sexyy Red (2023- present)

American rapper Sexyy Red could be Drake’s current girlfriend going by the rumours doing the rounds in Tinseltown. Speculations first ignited when Drake posted an intimate photo with Red on Instagram in July 2023, getting fans invested in the nature of their connection. The snapshot captured Drake, 36, planting a kiss on the cheek of the 25-year-old rapper, known offstage as Janae Nierah Wherry.

The post and subsequent sightings of the duo together hinted that their connection might extend beyond friendship. Adding fuel to the fire, Red referred to Drake as “her man” in the captions of some images, intensifying curiosity among their fans. The speculation peaked when they were seen posing for more intimate photos during a stop on Drake’s It’s A Blur tour in Inglewood, LA.

Despite the social media hints, neither Drake nor Red has publicly confirmed the true nature of their relationship. Drake’s romantic life has long been a topic of interest, with past rumours linking him to various celebrities.

(Main and featured image: Instagram/Drake/Rihanna/Jennifer Lopez)

This story first appeared on Augustman Singapore.

Frequently Asked Questions (FAQs)

– Who is Drake dating currently?
Drake is rumoured to be dating American rapper Sexyy Red.

– How long did Drake and Rihanna date?
Drake and Rihanna were in an on-again-off-again relationship for nearly 10 years, from around 2009 to 2016.

– When did Jorja Smith and Drake start dating?
Drake reportedly dated British singer Jorja Smith in 2017 for a couple of months. However, the exact timeline of their relationship was not publicly disclosed.