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Friends since 2005, Chris Brown and Rihanna went public with their romantic relationship in 2008.The couple went their separate ways after Brown pleaded guilty in June 2009 to assaulting the Barbadian singer on the eve of the 51st Grammy Awards.

THEY weren't quite Posh and Becks but Real Madrid's Karim Benzema used to date pop star Rihanna.Not that that's stopped the guys from veritably lining up to take their chances with the perennially unattainable artist."While we're on the topic of Instagram, I just wanna say it's a bit of an awkward vibe tonight.I gotta say, I've never been in the same room as so many guys who have DM'd my ex girl," Drake, who has publicly pledged allegiance to Ri Ri over the years, joked during his monologue while hosting the 2017 NBA Awards this week."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 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.

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