From Models to Singers! See Chris Brown’s Star-Studded Dating History: His Exes and Girlfriends

Rihanna

Rihanna was Chris’ first serious relationship in the music industry. Their romance first sparked in 2008. The pair dated until 2009, splitting up following his arrest for assaulting the “Unfaithful” singer on their way home from a pre-Grammys party.

Chris and Rihanna briefly rekindled their romance in 2012 but broke up eight months later.

Draya Michelle

Chris dated the Basketball Wives alum in 2009. The model explained on the Wendy Williams Show that they dated for nine months. “I kind of got him at a weak and vulnerable point I guess you could say,” she told Wendy Williams at the time, noting she never experienced any abusive behavior from her then-boyfriend. 

Karrueche Tran

Chris and Karrueche met in 2011, while she worked as a styling assistant on one of his projects. Karrueche found herself in a highly publicized love triangle with Chris Brown and his famous ex, Rihanna, after the “Say Goodbye” singer admitted he was “in love with two people.”

Chris and Karrueche called it quits for good in 2015 when she learned he was expecting a child with Nia Guzman. The stylist said Chris kept pursuing her after their split and she was later granted a 5-year restraining order against the singer in 2017, according to People.

Nia Guzman

Chris and Nia conceived their daughter Royalty in a one-night stand in 2014. The pair seemingly have a cordial coparenting relationship, with Chris being granted joint custody of Royalty in 2016. 

Agnez Mo

Angez and Chris collaborated on the 2018 single “Overdose”; around the same time, the “Sweet Love” singer posted cuddled-up photos with Agnez on his social media. It’s unclear if they actually dated, with sparks fizzling out after Agnez’s single was released. 

Vanessa Vargas

Vanessa and Chris sparked dating rumors in February 2017 after he posted her on his Instagram page. She commented “daddy” under the photo and was often spotted at L.A. hotspots. 

Ammika Harris

Ammika reportedly met the “No Guidance” singer in 2015, according to Hot New Hip Hop. The pair welcomed their son, Aeko Catori, in 2019 and split sometime that year.

It’s unclear where their relationship stands today as they were spotted spending Valentine’s Day in Paris together in 2023.

Diamond Brown

Diamond was first linked to the Virginia rapper after attending his 30th birthday party in L.A. in 2019. She was often spotted on tour with the singer and later gave birth to Chris’ third child, daughter Lovely Symphani in January 2022.