The Real Reason Why Drake And Rihanna Broke Up

Aubrey Drake Graham — better known as Drake — and Robyn Rihanna Fenty (a.k.a. Rihanna), have each been involved in some pretty high-profile romances, but most of their relationships with other celebrities haven't garnered nearly as much attention as when they decided to hook up with each other. The R&B songstress and Toronto rapper appeared to be the perfect couple on paper: they're both involved in the entertainment industry, they were both born outside of the United States, and they're both insanely hot. This sounds like a showbiz match made in heaven, right? Wrong!

Throughout the course of their respective careers, Drake and Rihanna have attempted to give their love and adoration for each other a shot, but things have never really seemed to go as planned. These two have shared an on-again, off-again relationship, complete with no labels and shrouded by an undefinable gray area. Aside from giving their fans whiplash with the constant ups and downs of their romance, it appeared that any chance this duo would drive off into the sunset together was officially squashed in October 2016. And, as of this writing, a happy ending for this pair just wasn't apart of "God's Plan."

So, what went wrong? Here are some of the reasons why Drake and Rihanna broke up.

Just a few months after she split from ex-boyfriend and fellow singer Chris Brown, who violently assaulted her in February 2009, Rihanna was spotted making out with Drake at a bowling alley in New York. "She was drinking whiskey and apple juice and making out with him all night. They were really cute together," an onlooker cited by Page Six claimed about their low-key date that May.

This would turn out to be the first of many times Rihanna and Drake would hook up, and just like the rest of their brief encounters, this one wouldn't last long either. Although the two began to see each other regularly, and Rihanna even asked Drake to pen a song for her — which was never released. However, Rihanna eventually decided to call it quits.

"I was a pawn," Drake told The New York Times in June 2010. "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." Womp, womp. Sounds like karma, no?

Following her first breakup with Drake, Rihanna conducted an interview with radio host Angie Martinez in November 2010, during which she described their relationship by saying (via CNN), "We weren't really sure what it was." When the radio host brought up Drake's aforementioned interview with The New York Times — in which he claimed he was treated like a "pawn" — Rihanna dispelled the notion entirely. "I definitely was attracted to Drake, but I think it is what it is, like it was what it was," the "Umbrella" singer said. "We didn't want to take it any further. It was at a really fragile time in my life, so I just didn't want to get too serious with anything or anyone at that time."

Oddly enough, after proclaiming she didn't want to get serious with anyone, Rihanna wound up going public with professional baseball player Matt Kemp less than a year later — however, that relationship wouldn't last long either.

This sounds like a case of Rihanna being fully aware that Drake wasn't the one. Perhaps her approach was a little savage, but we can't fault her for moving on.

After breaking up with professional baseball player, Matt Kemp, Rihanna and Drake reconnected in July 2011 and were spotted kissing inside a Montreal, Québec nightclub. Ooh la la. The following year, they made sweet music together in the recording studio, which resulted in their collaboration on the track, "Take Care." It appeared that AubRih was back and in full effect ... but Rihanna once again pumped the brakes on a full-blown reconciliation. Why must she toy with our hearts?!

The "Pour It Up" singer sat down with Oprah's Next Chapter in August 2012, and instead of talking about her rumored relationship with Drake, she dropped a bombshell by revealing she still had feelings for controversial ex Chris Brown. "We've built a trust again and that's it. We love each other and we probably always will," she said. When Oprah Winfrey asked if Brown was a true love for her, Rihanna replied, in part, "Absolutely. I think he was the love of my life. He was the first love and I see that he loved me the same way." 

No wonder Drake didn't stand a chance — but he wasn't prepared to bid Rihanna adieu just yet. 

Aside from Drake, Rihanna has been linked to various men in the entertainment industry, including Leonardo DiCaprio, as well as Ashton Kutcher and his That '70s Show co-star, Wilmer Valderrama. With her ever-changing love life, it's apparent that she's enjoying her time as one of show business' most eligible bachelorettes. However, there may have been an underlying issue that played a huge role in the "Rude Boy" singer's reluctance to maintain a committed relationship with Drake.

While speaking with Harper's Bazaar in July 2012 — just three months after their steamy "Take Care" collaboration — the songstress described her love life as "nonexistent." Rihanna then gave some insight into what appeared to be some intimacy issues. "If I come across someone who I find really cool, I'll hang out," she said. "But the minute I find that we're getting too close I just ... I don't let people in."

This on-again, off-again couple linked up at the start of 2016 to collaborate on Rihanna's chart-topping hit, "Work." A sizzling hot music video, which featured Drake, was later released, and the steamy chemistry between the two was undeniable. The Bajan superstar returned the artistic favor by lending her vocals to Drake's April 2016 song, "Too Good," and the duo took their love on the road to perform these tracks in front of packed crowds, complete with some major PDA to boot.

But before fans could ship the then-couple for the umpteenth time, Drake revealed on The Ellen DeGeneres Show (via Elle magazine) in May 2016 that he and Rihanna were "just friends." He contradicted that statement just a few months later when he gushed about his undying love for the "We Found Love" singer at that year's MTV VMAs (but we'll get more into that in a bit). By the time October 2016 rolled around, an insider told People magazine Rihanna and Drake were still together, but claimed their fling was "an open thing." The source also stated they had "spent a lot of time together and were really close but never considered themselves to be 'dating.'" 

In other words, it was basically a breakup redux, but could it really be considered a breakup if they technically weren't even dating? Your guess is as good as ours.

After attempting to reignite the flame in 2016, Drake and Rihanna abruptly called it quits in October of that year. According to an insider quoted by E! News, "Rihanna and Drake are seeing other people at the moment. They are not exclusive anymore. They still love each other, but their schedules have gotten in the way."

Unsurprisingly, Drake wasted no time putting himself back on the market and allegedly began hooking up with budding artist India Love. Now, here's where things get messy. There was some history between the parties involved, because Love's ex-boyfriend, Cliff Dixon, allegedly cheated on her with Rihanna! "Drake could be hooking up with India Love now to piss off Rihanna, which has clearly worked," a source claimed to the media outlet.

After the news broke that Drake had moved on, Rihanna posted a super petty message to her Instagram, which read, "None of my exes are married or in happy relationships so it's safe to say that I wasn't da problem lol." Burn! However, despite what appeared to be a less than cordial breakup, that same insider hoped the former couple would be able to work things out. "Anything can change between them though, for better or worse," the source continued. "They are still in each other's lives."

Following their 2016 breakup, and after yet another short-lived romance, Hollywood Life reported that Drake and Rihanna split once again — this time due to the rapper's supposed wandering eye, and, in particular, him getting a little too cozy with model Dakota Gonzalez.

"Drake reportedly took Dakota to an after-party for one of his concerts, and was showing her off!" the website reported, before stating Rihanna had also been photographed entering a New York City hotel with her ex-boyfriend, rapper Travis Scott. Her lyrics about cheating on a boyfriend on her 2006 track, "Unfaithful," where she sings, "And I know that he knows I'm unfaithful / And it kills him inside," are starting to make a lot more sense, aren't they?

It's clear Drake and Rihanna had the hots for each other, but since they were both allegedly playing the field and not too serious about being committed to each other, this fauxlationship was clearly doomed.

When it was announced that Rihanna would be the recipient of the MTV VMAs 2016 Video Vanguard Award, Drake went into overdrive to congratulate her. He started out by renting a billboard that displayed a message, which read, "Congratulations to Rihanna from Drake and Everyone at OVO [Sound record label]." Aww!

The rapper also pounced on the opportunity to present Rihanna with the coveted award during the televised ceremony, during which he stood on stage and publicly professed his undying love for her in a heartfelt speech. "She is someone I have been in love with since I was 22 years old. She is one of my best friends in the world," he said. At the end of his speech, Drake even went in for a kiss, but he was greeted by Rihanna awkwardly turning her head, forcing him to settle for a peck on the cheek instead. Cringe!

Despite that awkward moment, the entire world swooned, and Rihanna appeared to be loving the moment, too. But as she looked back on the incident for a June 2018 Vogue cover story, she said, "Waiting through [Drake's] speech was probably the most uncomfortable part. I don't like too many compliments; I don't like to be put on blast." Unsurprisingly, and as previously mentioned, the on-and-off couple headed to splitsville once again just two months after the awards ceremony. Rihanna told the publication, "We don't have a friendship now, but we're not enemies either. It is what it is." 

After Rihanna and Drake split — and after the songstress revealed that she and Drake no longer speak — he famously collaborated with her abuser. In July 2019, Drizzy featured on a Chris Brown track called "No Guidance," which boasted a music video showcasing Breezy and Drake in a dance-off.

Of the somewhat surprising collab, Drake explained to Rap Radar, "We've come together before and tried to link and make music, and I think we were always kind of forcing it. I think there was always resentment on both sides. You know, really at the end of the day, when you kind of step away from it and break it down, you start to feel silly 'cause it's over girl stuff, you know? But obviously, that can snowball into real s**t, and that's what happened in this situation."

Naturally, Drake was criticized for seemingly trivializing the fact that he and Brown didn't both just date Rihanna, but that Brown had infamously battered her. However, he insisted that he didn't want Rihanna to ever feel disrespected, adding to Rap Radar of his feud with Brown, "I think we just both grew up to the point that that person that was in the middle of us is like, no longer a part of either of our lives currently, and I have the utmost love and respect for her. I think of her as family more than anything."

While Rihanna was spotted hanging out at Drake's birthday party for several hours in October 2019, she was still in a relationship with businessman Hassan Jameel. However, spies claimed to E! News at the time that Drake appeared excited and happy to see her, with The Shade Room alleging that the rapper even had McDonald's delivered to the nightclub where she and her pals partied in his honor.

By January 2020, it was reported that RiRi and Jameel had officially called it quits ... and not long afterward, the music starlet was spotted spending time with Drake once more. Rihanna and the former Degrassi star made headlines when they were photographed together while attending the Yams Day benefit concert at the Barclays Center in Brooklyn. However, it should be noted that they didn't appear particularly close. Not to mention, at the same event, the "Diamonds" singer was also spotted getting allegedly cozy with rapper A$AP Rocky. According to The Sun, the two reportedly shared a hotel suite in the Big Apple. 

While tabloid hearsay is often just that, and Drake and Rihanna appear to be on good terms these days, it does seem quite possible their ship indeed sailed a long time ago.