A$AP Rocky, Drake, Hassan Jameel feature in Rihanna’s dating timeline

Rihanna stepping out with A$AP Rocky has been the talk of the town recently, especially when they both showed up at Drake’s spot early this week. News hinted at the Canadian singer, ‘not vibing’ to the “We Found Love” singer’s new guy. Could this be because he too is one of her exes?

When it comes to exes, bad girl Riri has an impressive catalogue of them. Below, we have created a timeline of Rihanna’s dating history up until 2021.

Chris Brown – 2007 to 2009

A$AP Rocky, Drake, Hassan Jameel feature in Rihanna's dating timeline

In 2007, at the start of her career, Rihanna was linked with Chris Brown, a multi-talented American singer and dancer. With Brown being 18 at the time and Rihanna just turning 19, their relationship was the centre of media attention. They were both just gaining a strong footing in their careers.

However, in February 2009, they ended the relationship after months of media speculations about domestic violence. Brown was later charged with assault and making criminal threats.

Drake – 2009 to 2016

A$AP Rocky, Drake, Hassan Jameel feature in Rihanna's dating timeline

As already mentioned in the beginning, Drake appears to be one of the regular features in Rihanna’s dating profile starting from 2009 up until 2016 and once again rearing his head in 2021.

The Canadian hitmaker has never been ‘officially’ confirmed to be dating the Fenty Beauty boss, but the rumours have been persistent over the years. They have done songs together that went on to be massive hits such as “What’s My Name”, “Take Care”, and “Work”. Their professional relationship was strong until Rihanna revealed to Vogue in a 2018 interview that she was no longer friends with Drake.

Yet, she turned up at his birthday in 2019 and she took her new lover to his spot in 2021. Their on and off relationship has spanned 21 years.

Matt Kemp – 2010

A$AP Rocky, Drake, Hassan Jameel feature in Rihanna's dating timeline

American professional baseball outfielder Matt Kemp dated Rihanna in 2010 but their relationship faced schedule constrictions. According to sources close to Kemp, to keep the relationship going, the athlete had to fly around the world with the singer who at the time was at the peak of her career.

They broke off things within 11 months of dating and they have both gone their separate ways since.

Chris Brown – 2012 to 2013

Why are Rihanna's comments about Chris Brown trending today?

The two singers appeared to fixed their initial relationship problems about two years after their messy breakup. However, it took until the start of 2013 for Rihanna to admit rekindling her relationship with Chris Brown in an interview with Rolling Stone.

By May 2013, the lovers went their way again, with Chris Brown confirming the break up publicly. There was no scandal this time around.

A$AP Rocky – 2013

In 2013, the “Diamonds” crooner was rumoured to be in a romantic relationship with Rakim Athelaston Mayers, popularly called A$AP Rocky. Although, at the time, they had only collaborated to make the hit song “Fashion Killa”, the rumours about a romantic relationship kept flying around.

For the 2012 MTV Video Music Awards, they performed a medley of their hits, “Cockiness” and “We Found Love” at the Staples Centre in Los Angeles ending with this cute photo:

Both artists denied the dating rumours at the time and conceded that they were friends. We will see where their friendship leads to years later.

Travis Scott – 2015

Rihanna in Dsquared2 Shearling Jacket-Haus of Rihanna | Rihanna boyfriend, Travis scott fashion, Rihanna style

Travis Scott dated Rihanna for some months in 2015, according to E! Online. The entertainment magazine even claimed that the relationship was already very strong with the rapper being very much into Rihanna.

They were also spotted in public together many times including their first hangout at New York Fashion Week in 2015. Not quite long after, they called it quits.

Hassan Jameel – 2017 to 2020

A$AP Rocky, Drake, Hassan Jameel feature in Rihanna's dating timeline

In 2017, the singer entered a relationship with Saudi businessman Hassan Jameel. Not much was known of him until their relationship went public, thanks to relentless news outlets. Turns out that he was Deputy President and Vice Chairman of Saudi Arabia operations of the family-owned international conglomerate business Abdul Latif Jameel.

Interests in their relationship soared with both lovers doing their best to stay out of the public eye. They seemed very serious with one another but then, they split up in 2020. It proved to be Rihanna’s longest relationship stretch.

A$AP Rocky – 2021

New Details Emerge About Rihanna and ASAP Rocky's Relationship | Complex

The two appear to have now entered a romantic relationship after years of claiming to be friends. The rapper previously dated Kendall Jenner before he started an official relationship with Rihanna.

While they seemed to be more public about their affair in 2021, the media reported sighting them together in 2020. They even spent some time in Rihanna’s home country, Barbados with her friends and family in December 2020.

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About The Author


Obinna is a fiction writer from Lagos, Nigeria, and grew up loving comic book characters and superheroes. He watches lots of action films and writes entertainment and technology articles. He is also interested in science and how things work.

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