Celebrity relationships and friendships are a rare breed. These famous faces have their lives played out in front of the masses, whether it’s the good, the bad, or the straight-up shady. In Elite Daily’s new series, It’s Complicated, we’re highlighting the biggest celebrity “feuds” that took over Hollywood and dominated our Sunday brunches for weeks on end. We’ll take a deep dive into the lives and social media feeds of our favorite stars and dissect what happened in front of the camera, what went down behind the scenes, and everything you might have missed in between.
Drake and Rihanna have a seriously complicated past y’all. The two have collaborated on music together, created steamy music videos together, and have even been spotted around town together, sparking numerous rumors about their relationship status. Over the past 10 years, Drake and Rihanna’s quotes about each other have put Drihanna shippers through the wringer. At times it seemed like they were "on" and, other times, they were clearly "off." And now, they aren’t even friends anymore. Ugh. At least Drihanna stans will always have some of these golden (and cringe-worthy) quotes to hang onto.
2005: They first meet, and Drake later says it was almost love at first sight.
In August 2016, Drake presented Rihanna with the Michael Jackson Video Vanguard Award at the MTV Video Music Awards. In the speech, he described what it was like when they met in 2005. “The first time I met Robyn Fenty, it was 2005," he said. "She was shooting a music video at a restaurant called Avocado in Toronto. The song was ‘Pon de Replay…’" He went on to reveal that he fell in love with Rihanna not long after, but more on that later.
November 2009: Rihanna says Drake isn’t her type.
Ever since May 2009, rumors had been swirling that Drake and Rihanna were dating after the pair were reportedly spotted making out at Lucky Strike in New York City, according to Page Six. But RiRi addressed the speculation when she appeared on Angie Martinez’s radio show in November 2009. She basically shut the Drizzy dating rumors down, telling Martinez she liked "hot and older" men.
"Me and Drake, we’re friends," she said definitively. "We’re still friends."
June 2010: Drake seemingly opens up about the Lucky Strike hookup.
On June 1, a few of Drake’s songs from his highly-anticipated album Thank Me Later leaked online. One of the songs on the album was the sultry, yet melancholy, track "Fireworks." In it, he seemingly referenced the rumored Lucky Strike hookup. He then discussed the speculation surrounding that night with The New York Times on June 8. Unfortunately for him, Drizzy kinda put his foot in his mouth while doing so.
"I was a pawn," he said. "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 said. “I was like, wow, this feels terrible.” Oh boy!
That didn’t go down well with fans, which is why later that month, Drizzy spoke with MTV News to clear up any misunderstanding. "That’s a moment that I’ve been eager, sort of, to explain," he told MTV News on June 16, 2010. "I feel like when people write about it or try to take an excerpt from me describing it, it’s gonna sound negative. And in no way was it negative. I’m at one of the greatest places in my life — I’m on top of the world. I’m extremely confident, so it’s very rare that anybody, let alone a woman that I like, makes me feel nervous or makes me feel small. She’s just such an overwhelming and incredible person." Nice save.
January 2011: Drake gushes about Rihanna by name in his music.
Just two months after the release of their steamy collab "What’s My Name?," Drake hopped on Rick Ross’ "Made Men" and took a moment to sing (read, rap) Rihanna’s praises:
Sounds like he was still feelin’ her despite any awkwardness after his less-than-positive account of their 2009 fling.
September 2013: Drake plays coy about his history with Rihanna.
Ellen DeGeneres was not so "generes" with Drake when he appeared on her show, grilling him on his rumored relationships. She played a game where she showed him photos of different celebrities and he had to reveal whether he "dated her," he’s "dating her now," or he’s "kissed her once."
When RiRi’s picture was shown, he answered, "Yeah, great girl. We had our moment. Always support and have love for her.” Clearly, he didn’t really answer the question — at least not in the same way he was quick to deny kissing Nicki Minaj and dating Kim Kardashian. By avoiding the Rihanna question, he neither confirmed nor denied that he kissed or dated her. So, that’s still not totally clear.
February 2014: Drake is definitely still pining.
Less than six months later, Drake made it clear that Rihanna was still the girl of his dreams. "She’s the ultimate fantasy," he told Rolling Stone. "I mean, I think about it. Like, ‘Man, that would be good.’ We have fun together, she’s cool and sh*t. But we’re just friends. That’s my dog for life."
August 2014: Drake insists Rihanna is a "great girl."
Drizzy then spurred more rumors about his complicated relationship with Rihanna at OVO Fest on August 5. While performing "Days of East" (a track rumored to be about Rihanna) he had pictures of Rihanna and the number "6" running in the background, which had fans convinced Drake was referring to Rihanna as the devil.
He made sure to tell his fans that was not the case. "My album title is VIEWS FROM THE 6," he said in a tweet. "The 6 is Toronto. Rih is a great girl who I know is about to kill this tour with Eminem. It’s all love!!"
February 2016: Rihanna says she’s single.
Despite Rihanna attending Drake’s Coachella set in May 2015 and then collaborating with him on their steamy track "Work" in January 2016, by February, Rihanna was shutting down any and all dating rumors.
Rihanna appeared on The Ellen Show and revealed that she was too busy for men and, as a result, was currently single.
“I’m single right now,” she said. “And, it’s not that I’m like, ‘Oh, pro-single, yes, I hate men!’ I just think I have so much on my plate that I can’t even find the time to entertain a steady relationship or anything serious. Or even a text.” So, it sounds like she left Drake’s messages on read… ? Got it.
May 2016: Drake impersonates Rihanna and says they’re just friends.
Drake hosted Saturday Night Live and opened by making fun of himself and the tendency for everything he does to turn into a meme. In his monologue, he even impersonated Rihanna, before singing about his perplexing relationship with her: "I swear we only friends, friends, friends." Ugh…
Check out Drake’s impression at the 0:52 mark.
August 2016: Drake tells Rihanna he wants a baby.
OK, here’s where things got iffy again. Rihanna made a few surprise appearances during Drake’s Summer Sixteen tour. Before their Aug. 1 performance, Drake introduced Rihanna along with a special message. "You showed up two nights in a row for my city. You might have to go half on a baby," he said.
Woah, there! Drizzy is getting ahead of himself.
Actions speak louder than words, and Drake’s actions on August 26 were pretty loud, too. Ahead of the 2016 MTV Video Music Awards, the "God’s Plan" rapper bought a billboard in Los Angeles to congratulate Rihanna on being honored with the Michael Jackson Video Vanguard Award. The billboard read: "Congratulations to Rihanna from Drake and Everyone at OVO."
His over-the-top gesture didn’t go unnoticed. Rihanna posted a photo of the billboard to her Instagram with the caption, "When he extra," followed by a heart and trophy emoji.
On August 28, Drake presented Rihanna with the aforementioned award at the MTV Video Music Awards, and admitted he was in love with her in his speech. "We love the woman who hasn’t changed since day one. She’s someone I’ve been in love with since I was 22 years old," he told the millions of viewers tuned into the show. "She’s one of my best friends in the world. All my adult life, I’ve looked up to her even though she’s younger than me. She’s a living breathing legend in our industry." Such a sweet speech. Drake was clearly in his feelings.
May 2018: Rihanna reveals she and Drake are no longer friends.
Rihanna opened up about Drake’s infamous MTV VMA speech in an interview with Vogue, revealing it actually made her super uncomfortable (but in a sort of nice way?).
"Waiting through that speech was probably the most uncomfortable part," she shared. "I don’t like too many compliments; I don’t like to be put on blast.”
She also gave an update that shook Drihanna shippers to their core. "We don’t have a friendship now, but we’re not enemies either. It is what it is." Aww… I had such high hopes for the pair.
October 2018: Drake accepts Drihanna wasn’t meant to be.
Later, Drake seemed to finally come to terms with the fact that a life with Rihanna was not in the cards, telling LeBron James in an interview on The Shop that he’d moved on from his "fairy tale life" of settling down and having kids with Rihanna.
"As life takes shape and teaches you your own lessons, I end up in this situation where I don’t have the fairy tale, like, ‘Oh, Drake started a family with Rihanna and this is like so perfect," he shared. "It looks so good on paper. By the way, I wanted that too at one time.”
May 2019: Rihanna admits she’s done collaborating with Drake.
And here we are in the present day. Rubbing salt in my Drihanna-shipper wounds, Rihanna admitted to New York Times’ T Style Magazine that she and Drizzy won’t be on any joint tracks in the near future.
"Not anytime soon, I don’t see it happening. Not on this album, that’s for sure," Rihanna said. Ugh, and RiRi’s album is supposed to be dropping sometime this year. I would’ve hoped for some Drake on it, but the queen has spoken.
Sigh… Rihanna and Drake will always be my favorite celebrity couple that never really was. Even if they don’t get close again, I hope we can at least get another song together from the pair. Even if it’s in the not-so-near future. R10 perhaps?
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