Rihanna Dating Timeline, Relationship History, Past Boyfriends

With more than a decade in the spotlight, Rihanna Fenty’s love life has basically become almost more popular than her fabulous career. We have seen her fall in love and fall in love again with men who are not just musicians like her, but who come from other walks of life. From actors to athletes and multi-million dollar heirs, what we know about Rihanna Fenty is nothing short of fascinating.

Even if a glance at Rihanna’s relationship history would certainly bring up the abusive relationship she entered into with her singer colleague Chris Brown, she has also experienced sweet moments in her love life. The affair with Chris made headlines and dominated the internet very much, all for the wrong reasons.

That was before the Canadian singer Drake appeared, and recently Badgalriri, as she affectionately calls herself, was romantically linked to the handsome Toyota heir Hassan Jameel. Although it was no picnic on Loveville for the Barbadian pop star, the Rihanna date timeline was full of handsome, talented, and successful men.

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Rihanna Dating Timeline: Past Boyfriends and Relationship History 

Negus Sealy (2001 – 2003)

He’s only known as the first guy Rihanna Fenty showed up in public as her boyfriend, and that’s all. Apparently, they were a topic when Barbadian beauty was still on her way to mainstream promotion.

Rihanna and Chris Brown (2007 – 2013)

This is by far the most published dating timeline of Rihanna. Their relationship was burdened with bad media, which was not due to Chris Brown’s outbursts of anger and abusive tendencies. The problematic relationship began quietly in May 2007 and gained momentum in 2008, but after he unleashed his anger on Rihanna’s body after a disagreement between the two lovers, the couple allowed time for their affair in March 2009.

After leaving the singer with visible injuries, the electronic musician was given five years of probation and orders to stay away from Rihanna. Somehow the love they once shared made them rekindle the flame in October 2012, but it wasn’t meant to be, and in March 2013 it was all over again, and this time there seems to be no flame to bring them together again.

Rihanna and Josh Hartnett (2007)

Obviously, this was the result of a flirting moment the singer had. She was seen kissing the good-looking American actor and even confessed to falling in love with him, but the romance just couldn’t survive for long. Too bad, he looks really cool.

Matt Kemp (2010)

Rihanna and the Dodgers’ baseball player let us speculate until they finally confirmed that they were together. There was less drama in their romance, which may or may not have anything to do with the fact that Matt is not exactly in the showbiz circus. Rihanna sounded excited when she spoke in interviews about her new admirer and they attended public events together, not leaving out the PDA.

Rihanna and Drake (2010 – 2016)

Another headline on Rihanna’s dating timeline is her alleged romance with Canadian rapper Drake, who has never concealed the fact that he adores her. The duo has been the subject of much speculation for as long as we can remember. This is due to the numerous collaborations and the chemistry between the two, which is completely insane. The two surely look good together, but they never admitted that anything happened between them, but they never denied the attraction. Now that Rihanna is hanging out with her new Prince Charming, Drake on Twitter is a kind of toast with trolls mocking him.

Hassan Jameel (2016 – 2018)

Rihanna’s new beau has been swindled! The Saudi hero is Toyota heir Hassan Jameel, whose family reserves the sole right to sell Toyota cars in Saudi Arabia. The family’s net worth is a staggering $1.5 billion. Jameel joined the highly acclaimed Rihanna dating list in December 2016. The singer confirmed in a 2018 edition of Vogue that they are together. For now, there is no confirmation if they are still an item.

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Rihanna’s Other Hookups

Just as her career took off, Rihanna and rap legend Jay Z. became the subject of an infamous romantic entanglement. In 2006, rumors spread that the rapper had given her a music contract in exchange for sex. In 2007, Rihanna had a single date with actor Shia LaBeouf, but there was no chemistry between the two, so nothing came of it.

In 2015, singer and actor Leonardo DiCaprio made out a little, and that same year she and rapper Travi$ Scott were seen hugging at New York Fashion Week. Or maybe they’re just friends since they worked together in a cougar commercial.

Other notable personalities who cannot be removed from the busy Rihanna dating timeline include – Lewis Hamilton, Karim Benzema, ASAP Rocky, J.R. Smith, Ryan Phillippe, Dudley O’Shaughnessy, Josh Henderson, Soulja Boy, Rashard Lewis, Wilmer Valderrama, and Omarion Grandberry, with whom they were all romantically involved.