Chris Brown and Rihanna's Relationship Timeline

Chris Brown and Rihanna's whirlwind romance came to a tragic end in 2009. Since then the two have talked about each other in the public eye and have rarely been seen together — until recently. See this timeline of their romance and friendship.
ESSENCE.COM Feb, 09, 2009

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On October 12, 2012 Chris Brown posted a video declaring he's in love with two people - presumably both Karreuche and Rihanna. "It's just ... when you share history with somebody, then you tend to fall in love with somebody else, it's kind of difficult," said Brown. "Is [there] such a thing as loving two people? I don't know. I don't know if that's possible. But for me, I just ... I feel like that."

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Brown released a statement on October 4, 2012 confirming he and Karreuche were no longer dating and that he wanted to focus on his career and more. "I love Karreuche very much but I don't want to see hurt over my friendship with Rihanna," he said.

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Chris Brown and Rihanna are seen sitting together at Jay-Z's Barclay Center concert on October 4, 2012. Brown's arm was resting comfortably around Rihanna's chair as they enjoyed the concert.

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Rihanna tweeted her support for Brown on September 24, 2012, the day he would return to court after failing a drug test. She said, "I'm praying for you and wishing u the best today!" Brown replied with "Thank u so much." The judge let Brown off with a warning.

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At the 2012 MTV Video Music Awards in early September, Rihanna was seen greeting Chris Brown along with a number of other guests. The two were spotted having a private moment and even shared a short cordial kiss.

6 of 26 Photo Courtesy of OWN

Rihanna and Oprah Winfrey

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In February 2012, Rihanna shocked the world and asked Chris Brown to appear on the remix of her song "Birthday Cake." The Bajan singer soon returned the favor and guest appeared on "Turn Up the Music," from his Fortune album.

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At the start of 2012, Chris Brown made a public announcement that would not be conducting interviews anymore. Perhaps it was an attempt to dodge further questions about his rocky past with Ri-Ri.

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In March 2011, Chris Brown lost his cool on Good Morning America. Brown launched into an angry tirade after Robin Roberts asked about the 2009 assault against Rihanna. Brown apparently stomped off to his dressing room screaming and allegedly smashed a window with a chair. While no one in the studio saw him break the glass, sources say he was in the dressing room when it occured. Brown left the building with his shirt off. He later tweeted, "I'm so over people bringing this past sh*t up! Yet we praise Charlie Sheen and other celebs for their bullsh*t." He later deleted the tweet.

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On February 10, 2011 Rihanna's restraining order against Chris Brown was eased as a judge allowed the two to have contact with each other. The judge imposed the condition that Brown must not "annoy, molest or harass" Rihanna.

11 of 26 Getty Images

Chris Brown began dating Karrueche Tran in late 2010. Their romance would last over a year.

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In December 2009, Rihanna began dating baseball star Matt Kemp. The pop star told Marie Claire, "I smile for real this time," when asked about her budding romance and love. Unfortunately, it didn't last too long. The couple would spend nearly a year together before breaking up in late 2010.

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Chris Brown appears for an arraignment at the Superior Court of Los Angeles County on March 5, 2009 in Los Angeles. Brown was charged with two felonies for assault. He was sentenced to five years probation and 1,400 of community service.

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In late February 2009, just weeks after Brown's assault, speculation began to mount that the couple was reuniting. The two reportedly spent several days together at Diddy's Star Island mansion in Miami, Florida where Brown is seen here enjoying a jetski.

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The twosome appeared to be comfy and in good spirits at a Clive Davis' pre-Grammys party in Los Angeles on February 8, 2009. The fight between Chris Brown and Rihanna was prompted when she read a three-page text message from another woman on Brown’s phone. Authorities said Brown reacted by hitting her head against the passenger window. He then continued to drive while punching her with his right hand, according to reports.

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Rihanna and Chris Brown performed "Umbrella" at 2008's Jingle Ball. Their romance seemed picture perfect. The couple even managed to align their work schedules – even embarking on a tour together.

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As stated previously, Rihanna and Brown were seldom seen without the other in tow. Here the “Run It” singer gets silly with cameras as he shops with Rihanna in Paris in December 2008.

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The pair toured together for the first time in October 2008.

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Rihanna and Chris Brown attend the 2008 MTV Video Music Awards together. At their friendship and relationship seemed to be growing and getting more serious.

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The fashion trendsetter and the new prince of pop sit together at the 2008 BET Awards in Los Angeles. Rihanna performed "Take a Bow" that evening.

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Rihanna and Chris Brown enjoy the 2008 MTV Movie Awards at the Gibson Amphitheatre in Universal City, California.

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Brown and Rihanna attend Entertainment Weekly’s Toast to Antonio LA Reid in West Hollywood, California in February 2008.

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The lovely couple were seen getting close the night before 2008 Grammy Awards at Clive Davis' pre-Grammy party and concert. Although the two denied dating, they would make a number of public appearances together in the coming months.

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Chris Brown and Rihanna gave a critically acclaimed performance at the 2007 MTV Video Music Awards. The couple performed Rihanna's hit single "Umbrella."

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Rihanna attends Chris Brown's 18th birthday party at New York's 40/40 club on May 6, 2007.

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Here are a young Rihanna and Chris Brown on the red carpet of the 2006 Kids Choice Awards.