The Relationship History Of Rihanna

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The recently declared World’s Most Desirable Woman (at this year’s Guys Choice Awards) has had her fair share of real-life leading men. No surprise, as she is beyond talented, confident, and beautiful.   She’s kept up her popularity for years and there doesn’t seem to be any signs that she’s slowing down.  We decided to take a look at Rihanna’s past relationships.  Here are the lucky men who she has chosen to be close with in real life.


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Rihanna and Drake have dated on and off in the past but the two stars confirmed they were dating again more seriously this week when they were photographed holding hands. The pop beauty has been spending most of her time with her rapper beau over the last few weeks, which sparked the speculation that they were a couple again. The photo of them holding hands confirmed this. Earlier in the week RiRi flew into the capital to join Drake as he wraps the UK leg of his tour. TMZ claimed that they spoke with multiple sources close to the couple who confirm that the two are dating exclusively.


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Ashton Kutcher

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The handsome actor was rumored to have a fling with Rihanna after she was spotted leaving his house in 2012.  It was reported the pair had a secret eight-week fling, but Rih reportedly later denied the rumors, saying she was “single and happy.” So it’s still unclear what was going on there.

J.R. Smith

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The popstar was reported to be dating basketball player J.R. Smith in 2012. According to In Touch, the pair were seen holding hands and looking very close indeed in May of that year but neither confirmed the relationship. Rih posted an Instagram comment claiming the sportsman parties too hard before playoffs. Smith reportedly said he wasn’t worried about the comment but the two weren’t spotted looking close after that.

Dudley O’Shaughnessy

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RiRi’s rebound from her Chris Brown/Matt Kemp emotional rollercoasters  came in the form of former British Olympic boxing hopeful Dudley O’Shaughnessy. Sparks flew between the pair in 2011 after he co-starred in her “We Found Love” video together.  Their romance was unfortunately short-lived but they reportedly rekindled a little romance again last year but the reunion didn’t last long.

Ryan Phillippe

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In 2011, Rihanna was rumored to be secretly dating American actor and director Ryan Phillippe.  Their rendezvous came shortly after the Reese Witherspoon’s ex ended his relationship with fellow blonde actress Amanda Seyfried. Rihanna and Phillippe’ relationship was never confirmed.

Matt Kemp

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The singer dated American baseball player Matt Kemp for the better part of a year in 2010. Despite being regularly pictured looking happy, the pair reportedly struggled to keep their long-distance relationship going. Rihanna told the Mail Online at the time: “It’s really difficult because we are so far from each other most of the year and we both have very demanding schedules, it gets difficult at times but it is what it is.” They ended up splitting in December 2010.

Chris Brown

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In Rihanna’s most publicly turbulent relationship, her and singer Chris Brown were together for four years after they met in 2005. The pair were first pictured together in 2007 – although Brown said at the time that his relationship status was “single and ready to mingle.” But 26-year-old Rih was quick to back him up, and told MTV a year later: “We are best friends, honestly, like brother and sister.”  But they were spotted in May 2008 looking very couply and from then on they were pretty much inseparable. But the pair famously split when Brown infamously assaulted his stunning girlfriend up in 2009.

Josh Hartnett

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Amongst all that Chris Brown drama and around the time Rihanna was first becoming a big star, she dated hunky actor Josh Hartnett. The pair dated in 2007 and the star told 3am: “I’ve fallen for him big time.” Spilling the beans about the Pearl Harbor star, she grinned: “I would be lying if I told you we were not more than just friends.” Despite the promising start, the two split shortly after and Rihanna ended up back with Brown.

Shia LaBeouf

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In one of the shortest romances on the singer’s record, Rihanna reportedly went on one date with actor Shia LaBeouf in 2007 – around the time she split from Josh. The Transformers actor confirmed the date but said it never went beyond that. “It never got beyond one date. The spark wasn’t there,” he said.

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