Rihanna Dating Timeline, Relationship History, Past Boyfriends

With more than a decade spent under the spotlight, Rihanna Fenty’s love life has basically become almost more popular than her fabulous career. We have seen her fall in and out of love with men who are not just musicians like her but from other areas of life. From actors to athletes and multi-million dollar heirs, what we know of Rihanna dating timeline has been nothing but intriguing.

Even though a peek into Rihanna’s relationship history would definitely bring up the abusive union she got into with fellow singer Chris Brown, she has also had sweet moments in her love life. The affair with Chris made the headlines and dominated the internet a lot, all for the wrong reasons.

This was before Canadian singer Drake came along and recently, Badgalriri, as she fondly calls herself, has been romantically linked to handsome Toyota heir, Hassan Jameel. While it’s not been a bed of roses on Loveville for the Barbadian pop star, Rihanna dating timeline has been abuzz with handsome, talented and successful men.

Rihanna Dating Timeline: Past Boyfriends and Relationship History 

Negus Sealy (2001 – 2003)

Rihanna Dating Timeline
Rihanna and Negus

He is just known as the first guy Rihanna Fenty ever paraded as her boyfriend in public and that’s all. Apparently, they were an item when the Barbadian beauty was still working her way to mainstream prominence.

Chris Brown (2007 – 2013)

Rihanna Dating Timeline
Chris and Rihanna (image source)

This, by far, is the most publicized on Rihanna dating timeline. Their relationship was laden with bad media, no thanks to Chris Brown’s anger issues and abusive tendencies. The troubled relationship started on a low key in May 2007 and gathered steam in 2008 but after unleashing his anger on Rihanna’s body following a disagreement between the two lovers, the couple called time on their affair in March 2009.

Having left the singer with visible injuries, the electronic musician was handed five years of probation in addition to an order to maintain a good distance away from Rihanna. Somehow, the love they once shared saw them rekindle the flame in October 2012 but it wasn’t meant to be after all and in March 2013, it was all over again and this time, it seems there’s no flame left to lead them back to each other.

Josh Hartnett (2007)

Rihanna Dating Timeline
Josh and Rihanna (image source)

Obviously, this was the result of a flirty moment the singer had. She was spotted kissing the handsome American actor and even confessed to having fallen for him but the romance just couldn’t survive for long. Too bad, he looks really cool.

Matt Kemp (2010)

Rihanna Dating Timeline
Rihanna and Matt

Rihanna and the Dodgers baseball player had us speculating until they finally confirmed they were dating. 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 circle. Rihanna sounded excited when she talked about her new beau during interviews and they attended public events together, not leaving out the PDA.

Drake (2010 – 2016)

Rihanna Dating Timeline
Rihanna and Drake (image source)

Another headline hogger on Rihanna dating timeline is her supposed romance with Canadian rapper Drake who has never hidden the fact that he adores her. The duo has sparked a lot of speculations for as long as we can remember. Blame it on the numerous collaborations and the chemistry between them which is totally insane, these two surely look good together, however, they never acknowledged anything happened between them but never denied the attraction though. Now that Rihanna is hanging out with her new prince charming, Drake is kind of toast on Twitter with trolls taunting him.

Hassan Jameel (2016 – 2018)

Rihanna Dating Timeline
Rihanna and Hassan (image source)

Rihanna’s new beau is guaped! The Saudi hunk is the Toyota heir named Hassan Jameel whose family reserves the sole right to sell Toyota cars in Saudi Arabia. The family’s net worth is a hair-raising $1.5 billion. Jameel entered the much-publicized Rihanna dating timeline in December 2016. The singer confirmed they are dating in a 2018 issue of Vogue. For now, there’s no confirmation if they are still an item.

Read Also: Beyonce’s Relationship Through The Years – Who Has Beyonce Dated?

Rihanna’s Other Hookups

Just when her career was picking up steam, Rihanna and rap legend Jay Z became the subject of a notorious romantic entanglement. Rumors went viral in 2006, saying the rapper gave her a music deal in exchange for sex. In 2007, Rihanna went on a single date with actor Shia LaBeouf but there was no chemistry between them, thus, nothing came out of it.

In 2015, the singer and actor Leonardo DiCaprio messed around a bit and also in the same year, she and rapper Travi$ Scott were seen at New York Fashion Week, hugging things out. However, they might just be friends since they worked together in a Puma ad.

Other notable personalities who cannot be removed from the ever-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, all of who she has been romantically linked to.


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