The Truth About Drakes Relationship History

When he’s not busy dissing Kanye West or causing an uproar by collaborating with the reviled R. Kelly, Drake can be spotted with many a fetching lady on his arm. He may consider his various dalliances with women to be part of “God’s Plan,” but not all of his exes would agree.

To truly understand Drake’s complicated relationship history, it’s important to unearth what the Canadian superstar looks for in a potential partner. For instance, has Drake ever met Miss Right? “I have come across it a few times, I’ve yet to be able to hold onto it, for whatever reason,” he ruminated on the “Rap Radar” podcast. “I’m the captain of a ship, and I look behind me and I see a lot of people on board… Hopefully I can find somebody that can just stand beside me at the wheel and help me steer while we keep the journey going as opposed to me having to pull over because that person is getting seasick.”

Self-styled “Legend” Drake may very well think of himself as the next Barney Stinson, but even he didn’t technically break the bro code. So, without further ado, let’s explore his colorful relationship history: it’s going to be legen — wait for it — dary.

Drake claims Rihanna treated him like a 'pawn'

When two stars as big as Drake and Rihanna get together, fireworks are pretty much inevitable. Quite literally. Drake’s track “Fireworks” is about Rihanna; the rapper told Elle that RiRi “hurt” him, propelling him to write the song, which includes the lyrics “I could tell it wasn’t love / I just thought you’d f***ed with me / Who could have predicted/ Lucky Strike would have you stuck with me.” But first, let’s look back on how it all started.

“The first time I met Robyn Fenty was 2005. She was shooting a music video at a restaurant called Avocado in Toronto,” the “Degrassi” alum explained in 2016 at the VMAs, adding, “I was introduced to her as a kid who played background music at a restaurant as people ate pasta.” 

In terms of their romantic relationship, the pair were first spotted getting cosy together in 2009 when Page Six reported that they were “locking lips.” Just one year later, the hip-hop superstar discussed his relationship with Rihanna with great rancour, telling The New York Times that she treated him like “a pawn.” However, did acknowledge that her supposedly objectionable treatment of him mirrored his own treatment of past girlfriends. “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,” he mused. “I was like, ‘Wow, this feels terrible.'”

Drake sang a different tune at the VMAs

When presenting Rihanna with the coveted Vanguard Award at the 2016 VMAs, Drake did a full 180 following his previous admonishment of the songstress by declaring his undying love for her. “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,” he said of his frequent collaborator. What made this revelation less than palatable was the fact that when RiRi went to give him a hug and receive the Moonperson statue, Drake planted what sure seemed to be an unexpected and unwanted kiss on her. After their one-sided embrace, she turned to him and appeared to say, “That wasn’t funny.” And then, she took the mic, shook off the arguably awkward interaction, and delivered her acceptance speech. Following the show, Rihanna wrote on Instagram, “@champagnepapi your speech was so touching and I love you for that!”

Two years later, she made it clear that she wasn’t totally into that VMAs moment. She told Vogue that she was on edge throughout Drake’s speech (“I don’t like too many compliments; I don’t like to be put on blast”), and the mag observed that she “winces slightly” upon hearing Drake’s name. “Waiting through that speech was probably the most uncomfortable part,” she admitted before making quite the bold claim, entirely disparate from Drake’s “best friends” declaration at the award show. The singer clarified, “We don’t have a friendship now, but we’re not enemies either. It is what it is.”

Tyra Banks and Drake enjoyed a Disneyland trip

Ellen DeGeneres may be in hot water due to her controversial behavior, but back in 2013 she was flying high. Based on the intimate questions she asked Drake during his appearance that year, it’s not hard to see why DeGeneres has become such a contentious figure in retrospect.

During his appearance on “The Ellen DeGeneres Show,” the host asked Drake whether he had ever dated Tyra Banks. The rapper admitted to having a brief dalliance with the “America’s Next Top Model” presenter in 2012. “We went to Disneyland in disguise actually, which was fun,” he said. “I don’t know if it was a date. It was a get together. We’re close as well.” A Disneyland date with Drake and Tyra Banks certainly sounds like quite the sight to behold, but the model didn’t take too kindly to Drake’s divulgence.

Chatting with Steve Harvey, Banks said, “People are going crazy, and I’m just like, ‘It’s not fair.’ And Drake, I have words for you.” With that, she launched into a freestyle about “Mr. Aubrey,” calling him “a lion going on ‘Ellen’ but not lying.” It’s pretty clear that things aren’t great when someone refers to their alleged ex-partner by their given name, so maybe Mr. Aubrey Drake Graham should think twice the next time he decides to kiss and tell.

Kat Dennings didn't call Drake back after their date

In the aforementioned “The Ellen DeGeneres Show” interview, Drake also confessed to having a thing for “2 Broke Girls” star Kat Dennings, with whom he went out with just once. “They don’t call me back after one date according to this,” he joked to DeGeneres. Based on his relationship history, it appears as though Drake is not wrong.

Dennings acknowledged that she did indeed go on a brief outing with the rap megastar, but she went on to discuss the verbal abuse she received from Drizzy stans once they suspected she might be linked to him. In an interview with Chelsea Handler (via E! News), Dennings explained that Drake happened to mention her on Twitter one time, which gave her “like, 50,000 new followers out of nowhere.”

Unfortunately, the actor soon realized that these new followers were merely hopping onto her socials in order to troll her, but she stated that Drake was nothing short of a gentleman in uplifting her in the wake of the bombardment of unpleasant DMs. “They were like, ‘F**k you, Kat Dennings’ and ‘You can’t take Drake from me,'” she recounted. “And then I realized what had happened, and then we started talking and he’s super, super nice.”

Was it 30 love for Serena Williams?

Serena Williams may be happily married to Reddit co-founder Alexis Ohanian, giving us all the feels with her wholesome family snaps on the ‘gram, but back in the early to mid 2010s, she was rumored to be dating Drake. In 2015, TMZ published snaps of Drake and Williams seemingly smooching, but their relationship predates that: Four years earlier, they sent each other racy tweets. In an innuendo that perhaps should have been reserved for the DMs, Drake wrote, “@serenawilliams I cannot wait to put it on you and make you sweat……….during our match this weekend.”

Then, in 2013, Drake name-dropped the tennis star in his song “Worst Behavior,” rapping, “I’m with my whole set, tennis matches at the crib/ I swear I could beat Serena when she playin’ with her left.” A year later, Williams spoke favorably about Drake to Vogue; when queried about the funniest person she knows, the tennis player replied “Aubrey.” As Billboard noted, Drake also eagerly watched Williams at Wimbledon in 2015.

But the commendatory allusions to Williams in Drake’s songs grew shady as the years passed. His 2017 track “Nothings into Somethings” appears to reference Williams’ engagement to Ohanian (MTO News notes that Ohanian’s “official Reddit handle is “Kn0thing””): “Did I just read that you just got engaged on me? / I heard from your friend, you couldn’t even tell me? / Or better yet, wait on me.” Ouch. By this point, Drake wasn’t throwing shade — he was hurling the whole tree.

Drake fended off rumors that he dated a teen

From Hadid (more on her later) to Harris, there’s just something about women named Bella. Or, in this instance, girls. Around 2016-2018, there was a longstanding rumor that Drake dated Bella Harris, the daughter of acclaimed R&B songwriter Jimmy Jam, when she was a teenager.

As E! News recounted, the Canadian megastar was spotted with Harris at the 2016 American Music Awards when she was just 16 and he was 29. That year, she professed to MissGuided that she’s a fan of Drizzy’s music: “The last song I played was ‘Fake Love’ by Drake,” she told the publication in an admission that would prove prophetic. Also that year, she posted a snap of herself and Drake on Instagram (via E! News) above the caption “No place I’d rather be,” though she has since deleted all posts pertaining to him. Vice ran with the unsubstantiated story and branded Drake a “creepy old man.”

E! News also reported that the pair allegedly went for dinner in Washington in 2018. However, both parties have denied that this is true, with a source telling ET that “Drake and Harris are not and have never been dating.” It seems that the two are merely good pals, just like Drake is with actor Millie Bobby Brown, as hard as it may be to fathom a meaningful friendship between a hip-hop star and a British teen. Well, stranger things have happened…

It was a sister act with India Love and Crystal Westbrooks

With the release of his fourth album, “Views,” 2016 was a busy year for Drake, not least because he was reportedly flitting between sisters India Love and Crystal Westbrooks. Dating siblings is a shock move even for the Certified Lover Boy; sisters should share and care, but this is another level. Accordingly, the elder sister, Crystal Westbrooks, had some words for Drizzy.

A source claimed to the Mirror that “Drake and India Love have been hooking up for at least a few weeks.” The elder Westbrooks, who previously had a thing with Drake, did not take too kindly to this news. In a series of since deleted tweets obtained by the publication, she wrote, “That awkward moment when she hops on your exes….. Nvm nvm nvm [sic] #iFeelLikeRayJ. I need answers sway.” According to The Sun, Crystal had claimed that she dated Drake during an episode of reality TV series “The Westbrooks,” while Perez Hilton alleged that Drake and Crystal attended Coachella together the previous year.

Crystal Westbrooks later apologized for throwing shade at her sister and swiftly deleted her Twitter account. In a succession of repentant and now deleted tweets (obtained by Hip Hollywood), she wrote “I reacted like an idiot to a story that I clearly knew nothing about” and “Lord deliver me from this messiness. Big sisters eff up sometimes too tho.” Drake hasn’t commented on this messy, sororal ménage à trois, but the drama would certainly make for intriguing lyrical content.

Things weren't always so rosy between Drake and baby mama Sophie Brussaux

Drake has an adorable son, Adonis, with erstwhile adult film actor Sophie Brussaux. It is unclear how and where the former flames met, but the rapper and Brussaux were first seen together in public in 2017, with the Mirror posting a series of images of the seemingly happy couple dining out. While they are now on benevolent terms, the relationship was once highly acrimonious.

In 2017, Brussaux alleged to TMZ that Drake ordered her to get an abortion when he discovered that she was pregnant. In texts obtained by the site, the rapper appears to admonish his ex, telling her “You do know what you’re doing you think you’re going to get money.” 

The drama was intensified by Pusha T, with whom Drake has long had beef, berating his rap peer in the song “The Story Of Adidon,” in which he accuses Drake of being a deadbeat dad who tried to hide the fact that he fathered a child with an adult film actor. On the heated diss track, Pusha T raps, “You are hiding a child, let that boy come home / Deadbeat mothaf***a, playin’ border patrol, ooh Adonis is your son/ And he deserves more than an Adidas press run, that’s real / Love that baby, respect that girl / Forget she’s a pornstar, let her be your world, yuugh!”

But now they're great co-parents, though Drake wishes he'd ended up with Rihanna

In an Instagram Story (via Daily Mail), Drake paid a sweet Mother’s Day tribute to his baby mama in 2021. Likewise, he dubbed himself “co-parent of the year” having “figured out a rapport” with Sophie Brussaux on his track “Champagne Poetry” from his sixth album “Certified Lover Boy.”

But Drake still isn’t over pining for Rihanna. During his appearance on HBO’s “The Shop”, he talked about his fling with Brussaux and admitted, “I end up in this situation where I don’t have the fairytale, like, ‘Oh, Drake started a family with Rihanna,’ like, so perfect… By the way, I wanted that.”

On telling his mom about Brussaux, Drake said, “It was tough for me to tell her that it’s somebody she’s never met. I am a single father learning to communicate with a woman who, you know, we’ve had our moments, right?” The rapper acknowledged that the publicity around his relationship with Brussaux could negatively affect his son, which is something he does not want: “But I don’t have any desire for him to like, not love his mother, or I don’t ever want the world to be angry at his mother. We have found ourselves in a situation, and we are both equally responsible.”

An exclusive source told Us Weekly that Drake and Brussaux “are very happily coparenting together in Toronto with both of them sharing custody.”

2017 was when Drake 'lost a J.Lo'

Her love don’t cost a thing, but Drake’s rumoured relationship with her sure did buy our attention. Whispers about a thing with Jennifer Lopez popped up in 2016 when J.Lo posted a series of cosy snaps on Instagram, in which the pair cuddled on a sofa and hung out backstage at the “On the Floor” star’s show (the latter of the two was accompanied by “#lovehim”). 

On 2018’s “Diplomatic Immunity,” Drake references his rumored romance with Lopez, rapping, “2017, I lost a J.Lo.” The lyrics, which, as Pitchfork noted, are arguably somewhat self-pitying, mirror Drake’s previous infatuations with famous women such as Rihanna and Serena Williams, who were also targets of his salty rhymes. Speaking of 2017, in May of that year, HollywoodLife reported J.Lo played a clip of “Hotline Bling” at her Las Vegas show and said, “Huh. Booty call.” 

In 2019, “Rap Radar” asked Drake if things with J.Lo were “real,” alluding to the theory that it was all for publicity. Drizzy said he has “plenty of love for her,” adding, “We had great times together, we were just hanging out at one point.” J.Lo has been relatively elusive about the nature of her relationship with Drake, telling Ellen DeGeneres that they were merely “hanging out,” but the $100,000 Tiffany Victoria diamond necklace that Drake reportedly gifted her (per People) suggests otherwise. Then again, maybe we shouldn’t be fooled by the rocks that she got.

His rumored romance with Bella Hadid provided ample lyrical content

Us Weekly reported that Drake threw supermodel Bella Hadid a star-studded birthday bash in October 2017, with Hadid captioning it “A perfect day” on Instagram. Just two weeks later, Page Six reported that Hadid’s former beau, The Weeknd, was beefing with Drake over the model. “They aren’t getting along right now,” a source alleged, adding, “[Drake] broke the bro code. They 100 percent hooked up.” 

A year later, Drake referenced Hadid not once, but twice, on his album “Scorpion.” The track “Sandra’s Rose” contains the lyrics “My house is full of supermodels just like Mohamed Hadid” in reference to the model’s wealthy real estate developer father. Likewise, on the song “Finesse,” Drake raps “You stay on my mind. You and your sister too hot to handle” in a probable nod to Bella and Gigi Hadid. A source for Us Magazine claimed that Drake ghosted Hadid shortly before the album’s release, though she has always dodged rumors that the pair dated, tweeting that they’re simply friends.

However, an unreleased song by Drake was leaked in 2020 and, yet again, he appears to bitterly pine for Hadid (and, it seems, her sister too). InStyle published the lyrics, which see Drake rapping, “Young slim baddies and they in Vogue / Yeah, I got 20 f**kin’ Gigis.” He apologized for the leak, but one thing is for sure: Drizzy sure wears his heart on his sleeve.

Drake had a fling with Layla Lace, but things soon turned ugly

Drake’s paternity scandals didn’t end with Sophie Brussaux. Just one month after impregnating Brussaux, Drake hooked up with Layla Lace, also known as Laquana Morris, who is an author according to her Instagram page. As per TMZ, Drake and Lace first got together in February 2017. After getting cosy backstage at a concert in Manchester, Drake conceded that he had a consensual one night stand with her. The outlet obtained text messages between the pair, in which Drake pines that he hopes to see Lace again soon, adding that “I love when u send me pics.”

But her account of that night was quite different and she went on to accuse Drake of rape and also alleged that he impregnated her. However, as the Independent reported, the British authorities cleared the rapper of sexual assault and it is unclear whether Lace was actually pregnant. “There is no credible evidence of pregnancy, or any baby, which would have been born last fall,” Drake stated in court documents obtained by the Independent.

Subsequently, he sued his erstwhile lover for extortion and defamation of character. The case was settled in 2018, and he reportedly shelled out $350,000, according to TMZ. 

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN’s National Helpline at 1-800-656-HOPE (4673).

Drake allegedly had a sex negative attitude towards Maliah Michel

Always one for OTT stunts, XXL reported that, during Houston Appreciation Weekend in 2017, Drake retired a number of jerseys embroidered with the names of different strippers, all of whom were reportedly in attendance. Adult entertainer Maliah Michel is another of Drizzy’s ex-partners and her name was on one such jersey.

It seems that Drake and Michel go way back, as he name-dropped her in his song “Miss Me” from his 2010 debut album “Thank Me Later.” On the track, he raps “Someone tell Maliah I’m on fire, she should work tonight.”

However, Michel’s account of the relationship was anything but rosy and she was enraged by Drake’s jersey stunt. In a series of tweets, she alleged that Drake had “been trying to make me stop dancing. Always putting me down about it.” She also wrote that he would say she’s “not better than anyone else in the club selling a** instead of dancing” and accused the rapper of belittling her. “I said Beyoncé wears the same kind of stuff I wear,” she posted. “[He] got mad and told me not to compare myself to Beyoncé.” Michel also called his behavior “mean and hurtful.”

Drake didn’t respond to Michel’s comments, but it seems he has a horde of angry ex-lovers on his case.

Deelishis said being with Drake was simply, well, delicious

With such a lengthy résumé of ex-lovers, there must be something that draws women towards Drake. Perhaps some insight from an alleged former flame can help elucidate the ever burgeoning bevy of girlfriends attached to Drizzy’s name.

Reality TV personality Deelishis (born Chandra Davis) is the winner of “Flavor of Love 2” and she has dished on her dalliance with the rapper. Their flavor of love? Well, according to her, it was quite delicious. “I was crazy about Drake,” she gushed during an appearance on TS Madison’s “Cracking The Cold Case” YouTube series in 2020, noting that “Drake is very passionate.” A year earlier, it was revealed during Deelishis’s appearance on “Dinner with the Avery’s” that she attended a Drake afterparty, so it’s possible that this is how the two met.

And may we not forget that 2015 interview with Kandi Burruss where she sang Drake’s praises. In a transcript published by All Hip-Hop, Deelishis was asked about her best lover ever, to which she replied, “He’s a rapper from Toronto… He’s excellent in bed.” She also told “The Real Housewives of Atlanta” star that she and the guy behind “Best I Ever Had” remain on amicable terms, which is certainly a pleasant change from his acrimonious breakups.

Has the Certified Lover Boy finally found the one in Johanna Leia?

It seems that Drake may have finally found the Miss Right he conjured in his Rap Radar interview. In 2021, TMZ reported that Drake started dating influencer and reality TV personality Johanna Leia. The rumored couple were snapped together at a high school basketball game, along with “Black Panther” star Michael B. Jordan. Leia’s son is Amari Bailey, who plays for Sierra Canyon School — yes, the same school where LeBron James’ son Bronny James plays. 

Drake reportedly dotes on Bailey with presents and grand gestures such as renting out Dodger Stadium for a date, according to TMZ. On his Instagram Story (via Radar Online), Bailey posted snaps of some pricey bling that Drake gifted him. As reported by Radar Online, the basketball player “showed off a diamond-encrusted ’10’ chain” and tagged Drake in his post followed by some colorful heart emojis. According to The Sun, Leia appeared to confirm dating rumors by posting a video on her Instagram Story with Drake’s song “Laugh Now Cry Later” playing in the background.

While Drake didn’t start the family with Rihanna that he so sorely wanted, his latest relationship can hopefully provide him with some familial bliss. Here’s hoping Drizzy’s in it for the long haul.

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