Chris Brown and Rihanna

This relationship might be one of the most controversial in Hollywood. Chris and Rihanna reportedly met in 2005, but only started dating in 2008. You know what happened next, the Umbrella singer worked with her lawyer to file a restraining order against her former beau, following the assault she experienced. However, despite the messy event that happened between the two, they eventually found love and also forgiveness, resulting in them continuing their love story in 2012. Sadly, it didn’t last that long as they split the following year. Rihanna opened up to Oprah that “true love” was what she found with Chris, and that she probably will love him always.

After the couple parted ways, Riri was romantically linked with rapper Drake. As of 2021, she has been in a relationship with A$AP Rocky. Meanwhile, Brown officially became a father after he impregnated his girlfriends, Ammika Harris and Nia Guzman.