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

• Rihanna and Chris Brown were one of the hottest couples in Hollywood in the early aughts
• They dated for about two years before breaking up after Chris assaulted Rihanna
• Rihanna and Chris seemingly have a civil relationship now, and Chris has supported her on social media several times

Rihanna, 34, and Chris Brown, 33, were one of the most talked about couples of the late aughts. The pair of hitmakers, who burst onto the scene in the 2000s with chart-toppers like “Pon de Replay” (Rihanna) and “Run It” (Chris Brown), were just teenagers when they made it big. The duo had their ups and downs over the course of their highly publicized relationship, and unfortunately, this included the 2009 incident during which Chris physically assaulted Rihanna. The assault, which earned Chris five years of probation plus community service, now greatly defines how people view their once seemingly perfect relationship and Chris’ career.

The physical assault transformed the wholesome R&B star into a pop culture villain, and although he has returned to making music — such as the 2018 hit “Freaky Friday” — his reputation has continued to be blemished with legal woes. Despite his continued run-ins with the law, it seems as though Chris has been able to make up with Rihanna and even strike up a respectful friendship with her — even after they tested another go at their relationship in 2013. Read on to learn about how Rihanna and Chris got together, where their relationship stands today, and what they are up to in their respective careers and lives.

When Did Chris Brown & Rihanna Meet?

Long before they were romantically linked, the pair met as teenagers in 2004, when Rihanna was 16 and Chris was 15. The duo was actually photographed backstage at the Z100 Jingle Ball concert held at Madison Square Garden in Dec. 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 a response tune to the smash hit titled “Cinderella”, in which he replaced some of the lyrics. One line had him fantasizing about the Barbados native being his “queen” (via Genius). The song was never officially released, but the pair performed it together a few times, showing that the chemistry between them was undeniable.

However, the pair vehemently denied any sparks between them. “We are best friends, honestly, like brother and sister,” Rihanna told MTV News (via BET) of their relationship in 2008. She later denied their romantic relationship after Chris reportedly admitted they were into each other. “He’s an amazing person, but we are not dating,” she said in 2008, according to BET. “We’re very close friends though. Very, very close.”

Rihanna’s attempts to smother any relationship rumors didn’t help, especially after they were spotted “getting cozy” at a Grammy Awards afterparty in 2008. Chris also reportedly sang happy birthday to the “Shut Up And Drive” singer at her 20th birthday celebration, according to PEOPLE. The pair finally confirmed their relationship later that year and quickly became the power couple of Hollywood

Chris Brown Is Arrested For Physically Assaulting Rihanna

On the day of the 2009 Grammys, fans were heartbroken to hear that Chris and Rihanna had abruptly canceled their highly anticipated performance. After much speculation, it was confirmed that the “Iffy” singer brutally beat Rihanna the night before, leaving her bruised and swollen. Disturbing photos showed the songstress in a hospital with a bruised face and black eyes.

Chris Spoke about the night he beat up Rihanna in his 2017 documentary, Chris Brown: Welcome To My Life. “My trust totally was lost with her,” he recalled, per PEOPLE. “She hated me after that. I tried everything, she didn’t care. She just didn’t trust me after that. From there, it just went downhill because there were too many verbal fights, physical fights as well. Mutual sides.” He later added that he felt like a “monster”.

Chris Brown was arrested and eventually charged with felony assault. 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. In 2011, a Los Angeles judge altered the order, allowing Chris to contact Rihanna without harassing her, per Reuters. 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. The pair rekindled their romance in 2012, and the Fenty Beauty founder spoke to Oprah Winfrey in a resurfaced 2012 interview about the relationship. 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 had 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 explained. During the brief period they were back together, the pair were spotted sitting courtside 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 Rihanna And Chris Are Today

Both Chris and Rihanna have moved on with other partners. Chris went on to father three children with three different girlfriends. Chris welcomed his first child, daughter Royalty, with Nia Guzman on May 27, 2014. Chris and Ammika Harris gave birth to their son Aeko on Nov. 20, 2019. Chris quietly welcomed his third child, Lovely, with his girlfriend Diamond Brown in Jan. 2022.

Despite being broken up for years, Chris continued to drop flirty comments on his ex’s Instagram snaps. For instance, he didn’t hold back in 2019 when Rihanna posted a picture in white lingerie to promote her Savage x Fenty line. “BOUGHT TO BREAK DA INTERNET. KEEP RISING QUEEN,” he commented, per Entertainment Tonight. He also requested that she drops new music.

As for Rihanna’s love life, the singer and fashion mogul dated Canadian-born rapper and singer Drake for many years. She began dating rapper A$AP Rocky in the weeks leading up to the 2020 holidays, and A$AP even joined Rihanna in Barbados to celebrate. “It’s a huge sign of how happy she is with him,” a source shared EXCLUSIVELY with HollywoodLife in Dec. 2020. “Rihanna is all about family so the fact that she invited him is very meaningful.”

The sweet couple surprised fans when they revealed they were expecting their first child in Jan. 2022 with a bumpin’ photoshoot. Their son was born in May of that year. Just nine months later, Rihanna revealed she is pregnant again during her Super Bowl halftime performance in Feb. 2023. On top of becoming a mother, Rihanna has stayed super busy building her fashion and makeup empires with Savage x Fenty and Fenty Beauty. She also confirmed she has continuously worked on music, despite not releasing an album sine 2016’s ANTI.

Rihanna nearly confirmed that she has music coming in 2023 during her cover shoot and interview with Vogue UK, which also debuted her son’s face for the first time publicly. “I want [to release music] this year,” she told the publication. “Like, honestly, it’d be ridiculous if it’s not this year. But I just want to have fun. I just want to make music and make videos. And I need the right background music with the visuals. I can’t just go shoot a video of me talking.”

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, he showed he is always going to be cheering on the “Work” hitmaker from the sidelines following her Super Bowl Halftime Show performance on Sunday, Feb. 12, 2023 by shouting her out on social media. RiRi’s Super Bowl LVII performance at the State Farm Stadium in Glendale, Ariz. marked her first live show in about seven years, and Chris made sure to shout her out with a sweet message of support on his Instagram Story. “Go girl,” he wrote, along with a heart and prayer hand emojis.

Chris Brown’s Reputation

As noted above, Chris has had several legal issues over the years, and his reputation precedes him. In Feb. 2023, Chlöe Bailey announced she collaborated with the “Forever” singer on her new song, called “How Does It Feel”. Unfortunately, both Chris and Chlöe, 22, received harsh criticism for their work, including from  Cheetah Girls alum Kiely Williams. Directly responding to Chlöe’s song announcement with a quote tweet, she complained, “Let him come out with his own record—so genius, so captivating that it makes us all forget HE BEATS WOMEN. He can’t so he wont.” She continued, “So what does he do? He slowly creeps back into the mainstream by getting small nods for features on Black Women’s merit. Black women who are more talented, more worthy, but give him the okay. I am swatting the f****** air rn. Garbage.”

Chris responded by making fun of 36-year-old Kiely’s lisp and star power. “Obviously you are at a point in your life where either you are very broke or broken. THE FACT you think you have to speak negatively about me makes u look so lame… YOUR LIFE AND CAREER MUST SUCK RIGHT NOW,” he wrote on his Instagram Story. “minding your business WOULDVE been best.. but I guess you don’t have a business or a real job that makes u financially stable. I feel more embarrassed for your actual maturity.”

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