By all accounts, they met as teenagers in 2005 and by 2006 were hanging out at events like the Nickelodeon Kids' Choice Awards. But even though they were seemingly attached at the hip, they kept insisting on their respective free agency, with Rihanna telling MTV News in 2008, "We are best friends, honestly, like brother and sister."
Just a few months later, Brown said in a radio interview, "Our relationship is growing. We started off as friends and we're getting a little bit closer now." It wasn't long before they assumed the throne as the prince and princess of pop-R&B, a power couple in the making.
The events of Feb. 8, 2009, are well-documented (as well as still speculated about), but they resulted in leaked police photos of Rihanna's bruised face shocking the world and Brown pleading guilty on June 23, 2009, to felony assault. He was sentenced to five years of probation and six months of community labor—a sentence that would set off a years-long legal odyssey for Brown that saw him being alternately praised for good behavior and punished for various other infractions.
"He was definitely my first big love," Rihanna told Diane Sawyer in November 2009, her first time speaking publicly about what happened. "The more in love we became, the more dangerous we became for each other."
That was hardly the end for them, as a 50-yard restraining order (Rihanna wanted it quashed entirely, but the judge insisted on at least 50 yards, 10 at industry events) didn't keep the two apart for the long haul. They would reunite off and on, including in 2012 when Brown guested on a remix Rihanna's racy track "Birthday Cake" and she joined him for "Turn Up the Music."
Confirming that they were dating once again, Rihanna told Rolling Stone at the beginning of 2013, "I decided it was more important for me to be happy and I wasn't going to let anybody's opinion get in the way of that. After being tormented for so many years, being angry and dark, I'd rather just live my truth and take the backlash. I can handle it."
Acknowledging their history, she added, "He doesn't have the luxury of f--king up again. That's just not an option. I can't say that nothing else will ever go wrong. But I'm pretty solid in the knowing that he's disgusted by that. And I wouldn't have gone this far if I ever thought that was a possibility. He made a mistake, and he's paid his dues. He's paid so much. And I know that's not a place he would ever want to go back to. And sometimes people need support and encouragement, instead of ridicule and criticism and bashing."
Though they would continue to hang out together amid breakup rumors, they seemingly split up for good in April 2013.