Rihanna and Chris Brown were one of the most infamous couples of the late noughties. The pair of hitmakers, who burst onto the scene in the 2000s with chart-toppers like “Pon de Replay” and “Run It” respectively, were just teenagers when they made it big. The duo had their ups and downs over the course of their tumultuous relationship, however the 2009 incident in which Chris physically assaulted Rihanna has come to define not only their relationship but also Chris’ career.
The once wholesome R&B up-and-comer transformed into somewhat of a pop culture villain, and has continued making poor choices even after his eventual split from Rihanna. In a resurfaced 2012 interview with Oprah Winfrey, which was released on September 2, Rihanna referred to Chris as her “true love.” So much has changed for the two stars, who have taken very different paths. Since the former couple’s final breakup in 2013, Rihanna has entered the world of fashion and beauty, and used her platform to influence incredibly change in areas of philanthropy. Chris has continued to work on his music, and has become a father to daughter Royalty and son Aeko. But let’s go back to the beginning. Take a look back at their relationship timeline.
When Did Chris Brown & Rihanna Meet?

Shortly after the success of Rihanna’s song “Umbrella”, which was the lead single on her album Good Girl Gone Bad and earned her a Grammy Award, Chris collaborated with her on a remix. He recorded an ‘answer song’ titled “Cinderella” in which he replaced some of the lyrics, set to the same beat. It marked the pair’s first musical collaboration, and he even took the stage with her during her tour in Asia to perform the remixed version live. The chemistry between the two was undeniable.
Chris and RiRi had plenty of on-stage chemistry together, and it was revealed in 2008 that the two were, in fact, dating. They arrived at the 2008 Grammys separately, but were reportedly getting cozy when they went inside the event. Just two days later, Chris sang for Rihanna at her 21st birthday and reportedly ended the song with a kiss. It wasn’t long before the duo were spotted by paparazzi jetting off to Rihanna’s native Barbados, and looking super loved-up wherever they went. All told, this seemed like one of the happiest times in their young lives, but circumstances would take a horrifying turn in 2009.
Chris Brown Is Arrested For Physically Assaulting Rihanna

Rekindling Their Romance & Their Final Breakup

She also revealed that she dropped the restraining order in 2011, and that she hd forgiven him. “It took me a long time. I was angry for a long time. I was resentful, I held a grudge. I was dark. I was angry. It was coming out in my music and my clothes and my attitude. I didn’t like that feeling. It was heavy,” she added. During the brief period they were back together, the pair were spotted sitting court side at basketball games and getting cozy on vacations together, however they split for good in 2013, with Chris confirming the news in May of that year.
Where The Two Are Today

As for Rihanna’s love life, the singer and fashion mogul has seemingly struck up a new romance with one of her longtime friends. Rihanna was spotted with rapper A$AP Rocky in the weeks leading up to the 2020 holidays. Although the two have maintained a low profile, Rocky spent the holidays with Rihanna in Barbados. It’s a huge sign of how happy she is with him,” a source shared EXCLUSIVELY with HollywoodLife in December 2020. “Rihanna is all about family so the fact that she invited him is very meaningful.”
Are Chris Brown & Rihanna On Good Terms?

As for Chris, it’s not entirely clear if the R&B recording artist has spoken about his former partner in the same way. Years have passed since Rihanna’s interview with Oprah in 2012, and both Chris and Rihanna are focused on their own work moving forward. Chris is seemingly recording more music, while Rihanna is taking over the world of fashion and beauty, as fans await her forthcoming studio album. Fans will have to wait and see if Rihanna and Chris Brown’s paths ever cross again.