When Did Chris Brown & Rihanna Meet? Chris Brown and Rihanna met in 2005 [Shutterstock]. Long before they were romantically linked, the pair met as teenagers circa 2005 when they were starting out in the music industry.

When was Chris Brown and Rihanna together?

The “Umbrella” singers first serious relationship began in 2008, three years after she launched her music career with her debut album, Music of the Sun. She and Chris Brown dated until February 2009, when he was arrested for physically assaulting her ahead of the Grammy Awards.