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

Chris Brown and Rihanna have had a tumultuous relationship over the years, which came to a head when he physically assaulted her in 2009. Take a look back at their 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. They 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.” Take a look back at their relationship timeline.

Rihanna & Chris Meet In 2005

Long before they were romantically linked, the pair met as teenagers circa 2005 when they were starting out in the music industry. Here, a baby-faced RiRi and Breezy are snapped backstage at the Z-100 Jingle Ball held at Madison Square Garden in December 2005.

The Singers Drop Their First Collab In 2007

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 collab, and he even took the stage with her during her tour in Asia to perform the remixed version live.

The Pair Confirm They’re An Item in 2008

Chris and RiRi had plenty of on-stage chemistry together, and it was revealed in 2008 that the pair 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.

Chris Is Arrested After 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, leaving her with a busted lip, black eyes and multiple bruises. Disturbing photos showed the songstress in hospital with a bruised and bloody face, and Chris was 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.

They Rekindle Their Romance In 2012

Much to the surprise of fans, RiRi forgave Chris several years later. 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, she said 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

Chris Continually Drops Flirty Comments On Her IG

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 continues 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.