Chris Brown & Rihanna’s Relationship Timeline: From First Kiss To Infamous Grammys Assault

Look back at Chris Brown and Rihanna’s relationship timeline.

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?

Long before they were romantically linked, the pair met as teenagers circa 2005 when they were starting out in the music industry. The duo was actually photographed at an event in 2005, where they looked bright-eyed and ready to take on their newfound stardom. A baby-faced RiRi and Breezy were snapped backstage at the Z-100 Jingle Ball held at Madison Square Garden in December 2005. From there, their paths continued to cross.

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

On the day of the 2009 Grammys, it was announced that the pair, who were slated to perform together, would not take the stage. As rumors began to swirl about why their number had been pulled, it was revealed that Chris brutally beat Rihanna the night before. Chris had busted her busted lip, and left Rihanna with black eyes and multiple bruises. Disturbing photos showed the songstress in a hospital with a bruised and bloody face following the verbal fights and physical fights that took place, and Chris Brown was arrested and eventually charged with felony battery. When the pair went to court in mid 2009, Chris pleaded guilty to the charges and was sentenced to five years of probation, as well as community service and domestic violence counseling. Rihanna also filed for a restraining order, and Chris was not allowed within 50 yards of her. The story completely rocked the world of pop culture. But there were still more chapters in Chris and Rihanna’s story together.

Rekindling Their Romance & Their Final Breakup

Much to the surprise of fans, RiRi forgave Chris several years later, following the events of the abusive relationship. The pair rekindled their romance in 2012, and she spoke to Oprah Winfrey about the relationship during an episode of Oprah’s SuperSoul Conversations. During the conversation, Rihanna confessed that Chris was her “true love,” and said that she considers him the “love of [her] life.” She added, “We’ve built a trust again, and that’s it. We love each other and we probably always will. That’s not anything that we’re going to try to change. That’s not something you can shut off if you’ve ever been in love.”

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

Both Chris and Rihanna have moved on with other partners. RiRi dated singer Drake for many years, while Chris went on to father two children with girlfriends Nia Guzman and Ammika Harris. Despite being broken up for years, Chris continued to drop flirty comments on his ex’s Instagram snaps. He didn’t hold back in 2019 when Rihanna posted a picture in white lingerie, as part of her Savage x Fenty line. “BOUGHT TO BREAK DA INTERNET. KEEP RISING QUEEN,” the commented, adding. “MUSIC SOON PLEASE.” Despite his attempts to get back in her good books, it seems these two have split for good.

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?

In the resurfaced 2012 interview that Rihanna did with Oprah, the singer alluded to a potential friendship between the pair. “We’ve been working on our friendship again and now we’re very, very close friends,” she explained. “I’m single,” Rihanna further clarified, shutting down any speculation that the two could have a romantic future. “But we have maintained a very close friendship ever since the restraining order’s been dropped. We’ve just worked on it little by little. It has not been easy.”

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.