Love on the brain! Rihanna and Hassan Jameel have allegedly split after nearly three years together, but her romances and flings with A-listers like Leonardo DiCaprio and Drake have kept fans captivated for more than a decade.
Scroll down for details on these relationships and more of RiRi’s dating history.
Rihanna was in a relationship with the “Heat” singer for a year by the time he physically assaulted her on the night of the 2009 Grammys. Brown was found guilty of felony assault and sentenced to five years of probation, six months of community service and one year of domestic violence counseling. The duo reunited briefly in 2012.
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Rihanna and her “Work” collaborator dated on and off from 2009 to 2016. “She doesn’t want to be held down,” a source close to the singer told Us Weekly in October 2016. A second source said, “They will always be close. If they end up together, it could happen, but not now.”
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The Honey Boy actor revealed in 2009 that he went on a date with the “We Found Love” singer two years prior. “[I was] filming a sword fight when I got the message [from Rihanna]. I said, ‘Can this be my life?’” he recalled to Playboy at the time, revealing that they decided to meet up in-person thereafter. “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
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The singer dated the Miami Marlins star between January and December 2010. “It was never as serious as it looked,” an insider told Us at the time. “It was always just [about] having fun.”
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Rihanna hooked up with the Shooter actor after crossing paths at a Gucci/Roc Nation brunch in February 2010, a source told Us. “She thinks he’s hot,” the source said. “They totally had sex. And it wasn’t even the first time!”
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The “Love on the Brain” performer spent Valentine’s Day 2015 weekend with the Oscar winner. “He thinks she’s incredibly hot,” a source told Us, specifying that neither one was “looking for a relationship” at the time. The following year, the duo reunited at a Paris nightclub and then hung out at Coachella.
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Rihanna reportedly reached out to the soccer star during the 2014 World Cup, and they stepped out for an early breakfast date in June 2015. “They’re definitely hooking up,” an insider told Us at the time, explaining that the relationship was not serious.
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The Barbadian spent time on a yacht in her home country with the Formula One race car champion in August 2015 after hanging out with him at the Grand Kadooment Day carnival days earlier.
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Rihanna got together with the Saudi Arabian businessman in 2017, and they were balancing his “serious” ways with her “fun and wild” personality for two years, as a source told Us in October 2019. “They’re polar opposites, but it works for them,” the source added. In January 2020, Us exclusively revealed that the couple had parted ways.
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Rihanna was rumored to be dating the “Wild for the Night” rapper after being spotted together following her January 2020 split from Jameel. Us exclusively confirmed in February 2020 that Rihanna and A$AP are “hanging out and hooking up.” The source noted that “they’re having fun and have always had chemistry.”
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On a May 2020 episode of the “Throwing Fits” podcast, cohost Lawrence Schlossman claimed that he “exposed” Scott’s low-key romance with Rihanna in Complex’s December 2015/January 2016 issue.
“I broke the news about him and Rihanna, which they told me not to do,” he explained at the time. “Apparently, what [Complex editor Joe] LaPuma, our boy Joe The Puma, told me was that it hurt Complex’s relationship with Travis. This was in 2015/16 I wrote this. But apparently, for the next couple of years, he would complain about that.
The former Complex editor added, “It’s not because he’s like, ‘Don’t tell anyone I’m smashing Rihanna.’ It’s because Rihanna’s like, ‘Don’t tell anyone that I’m smashing Travis Scott, please.” [It’s] obviously embarrassing as f--k.”
Us previously confirmed in September 2015 that the pair were “totally together” after they were spotted getting cozy at a party hosted in NYC, but they went their separate ways shortly afterward.
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