Drake and Rihanna have both been involved in some pretty high-profile romances, but
their relationships with other celebrities didn't generate nearly as much attention as
when they decided to hook up with each other. Here are some of the reasons why Drake and
Rihanna​ couldn't make their romance work.
In May 2009, Rihanna was spotted making out with Drake at a bowling alley in New York.
An onlooker told Page Six,
"She was drinking whiskey and apple juice and making out with him all night. They were
really cute together."
Although they began to see each other regularly, and Rihanna even asked Drake to pen a song
for her, they eventually decided to call it quits. In June 2010, Drake told The New York
Times,
"I was a pawn […] 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."
Following her first breakup with Drake, Rihanna told radio host Angie Martinez in November
2010,
"I definitely was attracted to Drake, but I think it is what it is, like it was what
it was. [...] 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."
However, after proclaiming she didn't want to get serious with anyone, Rihanna went public
with professional baseball player Matt Kemp less than a year later.
After breaking up with Kemp, Rihanna and Drake reconnected in July 2011 and were spotted
kissing inside a nightclub. The following year, they collaborated on the track, "Take
Care." But once again, their romantic relationship wasn't meant to be.
The "Umbrella" 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 her controversial ex, Chris Brown.
"We've built a trust again and that's it. We love each other and we probably always
will."
When Oprah Winfrey asked if Brown was her true love, Rihanna replied,
"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."
Basically, Drake didn't stand a chance.
The on-again, off-again couple collaborated on Rihanna's chart-topping hit, "Work," in
2016, and the chemistry between the pair was undeniable. Rihanna returned the favor by
lending her vocals to Drake's April 2016 song, "Too Good." But before fans could get too
excited, Drake revealed on The Ellen DeGeneres Show in May 2016 that he and Rihanna were
just friends. He teased,
"That's friendship at its finest right there."
"Who's time is it now though? Who's time is it king? Tell 'em."
"Drake."
"That's right boy!"
By the time October 2016 rolled around, an insider told People magazine Rihanna and Drake
were still together, but claimed,
"[I]t’s an open thing."
The source also stated,
"[Rihanna and Drake] spent a lot of time together and were really close but never considered
themselves to be 'dating.'"
After attempting to reignite their romance, Drake and Rihanna abruptly called it quits
in October 2016. 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."
After news broke that Drake had moved on with someone else, 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."
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]."
The rapper also pounced on the opportunity to present Rihanna with the award during the
televised ceremony in August 2016, during which he stood on stage and publicly professed
his undying love for her in a heartfelt speech. He adorably said,
"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."
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. Understandably,
the entire world swooned, even though the moment felt a little awkward. During an interview
with Vogue in June 2018, Rihanna reflected on the incident and 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."
As everyone knows, the on-and-off couple headed to splitsville once again, going their separate
ways in October 2016. Rihanna addressed the breakup in June 2018 when she told Vogue,
"We don't have a friendship now, but we're not enemies either. It is what it is."
Rihanna was spotted hanging out at Drake's birthday party in October 2019, but she was
still in a relationship with businessman Hassan Jameel, at the time. However, spies claimed
to E! News that Drake appeared excited and happy to see her, and a source revealed,
"Her and Drake were talking for a while and were smiling and laughing. It seemed like
a very pleasant interaction and they looked like they were having fun together as friends."
By January 2020, it was being reported that Rihanna and Jameel had officially called it
quits, and not long afterward, the superstar was spotted spending time with Drake once
more. They even made headlines when they were photographed together while attending the
Yams Day benefit concert at the Barclays Center in Brooklyn. However, at the same event, the
"Diamonds" singer was also allegedly spotted getting cozy with rapper A$AP Rocky. According
to The Sun,
“They shared a hotel suite during that trip in New York. [...] However, Rihanna is reluctant
to put a label on it as it’s so soon after Hassan. [...] They’re really enjoying each
other’s company and taking things easy as it’s still early days."
It seems as though Drake and Rihanna are on good terms again, after an on-again off-again
romance that spanned many years. But any fans hoping that the two musicians would end up
together are likely going to be disappointed.
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