{"id":296076,"date":"2025-05-15T20:55:31","date_gmt":"2025-05-15T20:55:31","guid":{"rendered":"https:\/\/newhampshiredigitalnews.com\/index.php\/2025\/05\/15\/chris-brown-rihannas-relationship-timeline-hollywood-life\/"},"modified":"2025-05-15T20:55:31","modified_gmt":"2025-05-15T20:55:31","slug":"chris-brown-rihannas-relationship-timeline-hollywood-life","status":"publish","type":"post","link":"https:\/\/newhampshiredigitalnews.com\/index.php\/2025\/05\/15\/chris-brown-rihannas-relationship-timeline-hollywood-life\/","title":{"rendered":"Chris Brown & Rihanna\u2019s Relationship Timeline \u2013 Hollywood Life"},"content":{"rendered":"


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Rihanna <\/strong><\/a>and Chris Brown<\/strong><\/a>\u00a0were 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 \u201cPon de Replay\u201d (Rihanna) and \u201cRun It\u201d (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<\/a>, 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\u2019 career.<\/p>\n

The physical assault transformed the wholesome R&B star into a pop culture villain, and although he has returned to making music \u2014 such as the 2018 hit \u201cFreaky Friday<\/a>\u201d \u2014 his reputation has continued to be blemished with legal woes<\/a>. 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 acquaintanceship with her \u2014 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.<\/p>\n

When Did Chris Brown & Rihanna Meet?<\/h2>\n
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Chris Brown and Rihanna met in 2005 (Photo: Shutterstock)<\/figcaption><\/figure>\n

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.<\/p>\n

Shortly after the success of Rihanna\u2019s song \u201cUmbrella\u201d, which was the lead single on her album Good Girl Gone Bad<\/em> and earned her a Grammy Award, Chris collaborated with her on a remix. He recorded a response tune to the smash hit titled \u201cCinderella\u201d<\/a>, in which he replaced some of the lyrics. One line had him fantasizing about the Barbados native being his \u201cqueen\u201d (via Genius<\/em><\/a>). The song was never officially released, but the pair performed it together<\/a> a few times, showing that the chemistry between them was undeniable.<\/p>\n

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Rihanna and Chris Brown perform at the 2008 Z100 Jingle Ball in New York City (Photo: Splashnews)<\/figcaption><\/figure>\n

However, the pair vehemently denied any sparks between them. \u201cWe are best friends, honestly, like brother and sister,\u201d Rihanna told MTV News<\/em> (via BET<\/em><\/a>) of their relationship in 2008. She later denied their romantic relationship after Chris reportedly admitted they were into each other. \u201cHe\u2019s an amazing person, but we are not dating,\u201d she said in 2008, according to BET<\/em>. \u201cWe\u2019re very close friends though. Very, very close.\u201d<\/p>\n

Rihanna\u2019s attempts to smother any relationship rumors didn\u2019t help, especially after they were spotted \u201cgetting cozy\u201d <\/a>at a Grammy Awards afterparty in 2008. Chris also reportedly sang happy birthday to the \u201cShut Up And Drive\u201d singer at her 20th birthday celebration, according to PEOPLE<\/em><\/a>. The pair finally confirmed their relationship later that year and quickly became the power couple of Hollywood.<\/p>\n

Chris Brown Is Arrested For Physically Assaulting Rihanna<\/h2>\n
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Chris Brown was arrested in 2009 for physically assaulting Rihanna, leaving her with multiple bruises (Photo: Shutterstock)<\/figcaption><\/figure>\n

On the day of the 2009 Grammys<\/a>, fans were heartbroken to hear that Chris and Rihanna had abruptly canceled their highly anticipated performance. After much speculation, it was confirmed that the \u201cIffy\u201d 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.<\/p>\n

Chris spoke about the night he beat up Rihanna in his 2017 documentary, Chris Brown: Welcome To My Life<\/em>. \u201cMy trust totally was lost with her,\u201d he recalled, per PEOPLE<\/em><\/a>. \u201cShe hated me after that. I tried everything, she didn\u2019t care. She just didn\u2019t trust me after that. From there, it just went downhill because there were too many verbal fights, physical fights as well. Mutual sides.\u201d He later added that he felt like a \u201cmonster\u201d.<\/p>\n

Chris 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<\/em><\/a>. The story completely rocked the world of pop culture. But there were still more chapters in Chris and Rihanna\u2019s story together.<\/p>\n

Rekindling Their Romance & Their Final Breakup<\/h2>\n
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Chris Brown and Rihanna rekindled their romance in 2012 before finally ending their relationship (Photo: MEGA)<\/figcaption><\/figure>\n

Much to the surprise of fans, RiRi<\/a> forgave Chris several years later. The pair rekindled their romance in 2012, and the Fenty Beauty founder spoke to Oprah Winfrey<\/strong> in a<\/a> resurfaced 2012 interview<\/a> about the relationship. During the conversation, Rihanna confessed that Chris was her \u201ctrue love\u201d and said that she considers him the \u201clove of [her] life.\u201d She added, \u201cWe\u2019ve built a trust again, and that\u2019s it. We love each other and we probably always will. That\u2019s not anything that we\u2019re going to try to change. That\u2019s not something you can shut off<\/a> if you\u2019ve ever been in love.\u201d<\/p>\n

She also revealed that she dropped the restraining order in 2011, and that she had forgiven him. \u201cIt 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\u2019t like that feeling. It was heavy,\u201d 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.<\/p>\n

Where Rihanna And Chris Are Today<\/h2>\n
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Rihanna and Chris Brown are seemingly on good terms, but they have not been seen together in years (MEGA\/BACKGRID)<\/figcaption><\/figure>\n

Both Chris and Rihanna have moved on with other partners<\/a>. Chris went on to father three children<\/a> with three different girlfriends. Chris welcomed his first child, daughter\u00a0Royalty<\/strong><\/a>, with Nia Guzman<\/strong> on May 27, 2014.\u00a0Chris and\u00a0Ammika Harris<\/strong><\/a>\u00a0gave birth to their son Aeko<\/strong><\/a> on Nov. 20, 2019. Chris quietly welcomed his third child<\/a>, Lovely<\/strong>, with\u00a0Diamond Brown<\/strong><\/a> in Jan. 2022.<\/p>\n

Despite being broken up for years, Chris continued to drop flirty comments on his ex\u2019s Instagram<\/a> snaps. For instance, he didn\u2019t hold back in 2019 when Rihanna posted a picture of herself rocking white lingerie to promote her Savage x Fenty line. \u201cBOUGHT TO BREAK DA INTERNET. KEEP RISING QUEEN,\u201d he commented, per Entertainment Tonight<\/em><\/a>. He also requested that she drops new music.<\/p>\n

As for Rihanna\u2019s love life, the singer and fashion mogul dated Canadian-born rapper and singer Drake<\/strong> <\/a>for many years. She began dating<\/a> rapper A$AP Rocky<\/a><\/strong> in the weeks leading up to the 2020 holidays, and A$AP even joined Rihanna in Barbados to celebrate. \u201cIt\u2019s a huge sign of how happy she is with him,\u201d a source shared EXCLUSIVELY<\/a> with\u00a0HollywoodLife<\/strong> in Dec. 2020. \u201cRihanna is all about family so the fact that she invited him is very meaningful.\u201d<\/p>\n

The sweet couple surprised fans when they revealed they were expecting<\/a> their first child in Jan. 2022 with a bumpin\u2019 photoshoot. Their son was born<\/a> in May of that year. Just nine months later, Rihanna revealed she is pregnant again<\/a> 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<\/a> and Fenty Beauty<\/a>. She also confirmed she has continuously worked on music, despite not releasing an album sine 2016\u2019s ANTI<\/em>.<\/p>\n

Rihanna nearly confirmed that she has music coming<\/a> in 2023 during her cover shoot and interview with Vogue UK<\/em><\/a>, which also debuted her son\u2019s face for the first time<\/a> publicly. \u201cI want [to release music] this year,\u201d she told the publication. \u201cLike, honestly, it\u2019d be ridiculous if it\u2019s 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\u2019t just go shoot a video of me talking.\u201d<\/p>\n

Are Chris Brown & Rihanna On Good Terms?<\/h2>\n
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Chris is now a father of three and Rihanna is building her brand in fashion and beauty as a mother of one (Photo: Shutterstock)<\/figcaption><\/figure>\n

In the resurfaced 2012 interview that Rihanna did with Oprah, the singer alluded to a potential friendship between the pair. \u201cWe\u2019ve been working on our friendship again and now we\u2019re very, very close friends,\u201d she explained. \u201cI\u2019m single,\u201d Rihanna further clarified, shutting down any speculation that the two could have a romantic future. \u201cBut we have maintained a very close friendship ever since the restraining order\u2019s been dropped. We\u2019ve just worked on it little by little. It has not been easy.\u201d<\/p>\n

As for Chris, he showed he is always going to be cheering on the \u201cWork\u201d hitmaker from the sidelines following her Super Bowl Halftime Show performance on Sunday, Feb. 12, 2023 by shouting her out on social media. RiRi\u2019s Super Bowl LVII<\/a> 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<\/a>\u00a0on his Instagram<\/a> Story. \u201cGo girl,\u201d he wrote<\/a>, along with a heart and prayer hand emojis.<\/p>\n

Chris Brown\u2019s Reputation<\/h2>\n

As noted above, Chris has endured several legal issues over the years<\/a>, and his reputation precedes him. In Feb. 2023,\u00a0Chl\u00f6e Bailey<\/a><\/strong> announced she collaborated with the \u201cForever\u201d singer on her new song, called \u201cHow Does It Feel\u201d. Unfortunately, both Chris and Chl\u00f6e received harsh criticism<\/a> for their work, including from Cheetah Girls<\/em>\u00a0alum Kiely Williams<\/strong><\/a>. Directly responding to Chl\u00f6e\u2019s song announcement with a quote tweet, Kiely complained, \u201cLet him come out with his own record\u2014so genius, so captivating that it makes us all forget HE BEATS WOMEN. He can\u2019t so he wont.\u201d She continued, \u201cSo what does he do? He slowly creeps back into the mainstream by getting small nods for features on Black Women\u2019s merit. Black women who are more talented, more worthy, but give him the okay. I am swatting the f****** air rn. Garbage.\u201d<\/p>\n

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Chris responded by making fun of 36-year-old Kiely\u2019s lisp and star power. \u201cObviously 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\u2026 YOUR LIFE AND CAREER MUST SUCK RIGHT NOW,\u201d he wrote on his Instagram Story<\/a>. \u201cminding your business WOULDVE been best.. but I guess you don\u2019t have a business or a real job that makes u financially stable. I feel more embarrassed for your actual maturity.\u201d<\/p>\n

If you or someone you know is experiencing domestic violence, please call the\u00a0<\/i>National Domestic Violence\u00a0Hotline<\/i><\/a>\u00a0at 1-800-799-7233 for confidential support.<\/i><\/p>\n

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