With more than a decade spent under Rihanna Fenty’s love life has become almost more popular than her fabulous career. We’ve seen her fall in love with men who aren’t just musicians like her, but from other walks of life. From actors to athletes to multimillion-dollar heirs, what we know about Rihanna’s dating timeline has been nothing but intriguing.
Although a peek into Rihanna’s relationship history would no doubt bring to mind the abusive union in which she entered into with fellow actor Chris Brown. She also had some good times in her love life. The affair with Chris made headlines and dominated the internet a lot, all for the wrong reasons.
That was before Canadian singer Drake came along, and recently Badgalriri, as she is affectionately known, was romantically linked to handsome Toyota heir Hassan Jameel. Even though the Barbados pop star didn’t get giddy in Loveville, the timeline of Rihanna’s encounters with her handsome, talented, and successful men.
Rihanna’s Dating Timeline: Past Boyfriends and Relationship History
Negus Sealy (2001 – 2003)
He’s just known as the first Rihanna Fenty guy ever to parade as her boyfriend in public and that’s it. Apparently, they were an item when the Barbadian beauty was still working to gain fame.
Chris Brown (2007 – 2013)
This, by far, is the most hyped on Rihanna’s dating calendar. Their relationship was fraught with bad media, not thanks to Chris Brown’s anger issues and abusive tendencies. The troubled relationship began quietly in May 2007 and escalated in 2008, but after unleashing their anger on Rihanna’s body following a disagreement between the two lovers, the couple announced the end of their affair in March 2009.
After leaving the singer with visible injuries, the electronic musician was sentenced to five years probation in addition to a restraining order 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. In March 2013, everything had to be redone and this time, it seems that there is no longer any flame left to bring them back to One and the other.
Josh Hartnett (2007)
Obviously, this was the result of a flirty moment the singer had. She was spotted kissing the handsome American actor and even confessed to falling in love with him, but the romance couldn’t last long. Too bad, he looks really cool.
Matt Kemp (2010)
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 something to do with Matt not exactly being in the showbiz circle. Rihanna seemed enthusiastic when she talked about her new boyfriend during interviews and when they attended public events together, without leaving aside the PDA.
Drake (2010 – 2016)
Another big headline on Rihanna’s dating timeline is her supposed romance with Canadian rapper Drake who has never made a secret of the fact that he adores her. The duo has sparked a lot of speculation ever since. Blame it on the many collaborations and the chemistry between them which is totally insane, these two surely go well together, however, they never admitted that nothing happened between them but they never denied the attraction. 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’s new beauty is ruined! The Saudi is Toyota heir Hassan Jameel, whose family reserves the exclusive right to sell Toyota cars in Saudi Arabia. The family’s net worth is $1.5 billion. Jameel entered Rihanna’s high-profile dating timeline in December 2016. The singer confirmed they were dating in a 2018 issue of Vogue. At the moment there is no confirmation if this is still an item.
Rihanna’s Other Hookups
Just as her career was picking up speed, Rihanna and rap legend Jay Z became the subject of a notorious romantic entanglement. Rumors went viral in 2006 claiming the rapper gave him a music deal in exchange for sex. In 2007, Rihanna went on a single date with actor Shia LaBeouf but there was no chemistry between them so nothing came of it.
In 2015, singer and actor Leonardo DiCaprio, the same year she and rapper Travi$ Scott were seen at New York Fashion Week, taking risks. However, they might just be friends since they worked together in a Puma commercial.
Other notable personalities who cannot be taken away from Rihanna’s ever-high-profile columns include Lewis Hamilton, Karim Benzema, ASAP Rocky, JR Smith, Ryan Phillippe, Dudley O’Shaughnessy, Josh Henderson, Soulja Boy, Rashard Lewis, Wilmer Valderrama and Omarion Grandberry, everyone she’s been romantically linked to.