The Rihanna dating timeline spans 18 years of Hollywood romances, private relationships, and public heartbreaks. From a teenage love affair to motherhood, follow every chapter of her incredible journey.

Chris Brown dominated this era with a passionate romance turned tragic. The 2009 assault rocked the world. A brief 2012 reunion proved the chapter was truly over. Matt Kemp offered a quiet four-month rebound in between.

Seven years of musical collaborations and romantic speculation defined this period. Drake declared his love on live TV at the 2016 VMAs, but Rihanna called it uncomfortable. Their chemistry produced hits but never a lasting relationship.

Saudi businessman Hassan Jameel gave Rihanna three peaceful years completely off the radar. She launched Fenty Beauty during this time and proved she could separate her public persona from her private heart.

ASAP Rocky went from longtime friend to the love of her life. Their sons RZA and Riot Rose completed the family Rihanna always wanted. She revealed her second pregnancy at the 2023 Super Bowl halftime show.