A look back at Chris Brown's dating history, from Rihanna to Karrueche Tran

Business Mayor

16-05-2025

Chris Brown has had quite the dating history. With three children from three different mothers and one particularly famous ex, the singer's past and current relationships have often come under scrutiny.
According to the Metropolitan Police, the singer has been charged with grievous bodily harm and remains in custody.
He is currently on tour and is scheduled to play several shows across the UK in June and July.
In the meantime, we take a look back at the some of the singer's notable romantic relationships.
Chris Brown and Rihanna
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Chris Brown dated Barbadian R&B legend Robyn 'Rihanna' Fenty back when both of them were still in the relative infancy of their careers. They met as teenagers in 2004, during their come-up. They were first photographed backstage at the Jingle Bell Ball in 2005, and their career paths repeatedly crossed, until they eventually ended up in a relationship in 2008.
They broke up for a period in 2009, though they later rekindled their relationship in 2012. 'We've built a trust again, and that's it,' Rihanna told Oprah at the time. 'We love each other and we probably always will. That's not anything that we're going to try to change. That's not something you can shut off if you've ever been in love.' The pair broke up for good in 2013. Despite their past, Chris congratulated Rihanna in 2022 on the birth of her child with A$AP Rocky.
Draya Michele
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Draya Michele, known for her appearance on Basketball Wives LA, dated Chris for about nine months in 2010, between his stints dating Rihanna. Discussing their breakup on a radio show, she said: 'We just went our separate ways and it was just too much fighting and too many differences. Arguing, sorry. I'm very jealous and I'm a very psycho crazy girlfriend. I act like everybody's baby momma.' After their breakup, they remained friends, and Chris introduced Draya to his future longterm girlfriend, Karrueche Tran. Karrueche Tran (2011–2015)
Karrueche Tran and Chris Brown
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Karrueche Tran, a socialite and actress, met Chris in 2011 while working as a styling assistant on one of his projects. At this time, she was relatively unknown in the public eye and had a job at Nordstrom in Los Angeles. Their relationship became complicated due to Chris's ongoing connection with Rihanna, something which was hinted at by his ex, Draya Michele. In that same radio interview where she explained their breakup, Michele explained: 'Me and [Chris] always remained friends, and then he was like I want you to meet my girlfriend [Karrueche Tran], she's so cool, meet her. I was like cool,' Michele recalled. 'I don't think I was the ex that she needed to be concerned about. So it was all good for me and her to be cool.'
In 2012, Brown allegedly ended his relationship with Karrueche to avoid hurting her because of his friendship with Rihanna. However, they reunited after Chris's relationship with Rihanna ended. In 2014, Chris Brown fathered a daughter, Royalty, with another woman, Nia Guzman, though he says he didn't know about his daughter until she was eight months old (Nia Guzman and Chris never reportedly dated and have always been cited as 'good friends'). In 2015, Karrueche publicly announced their breakup, citing Chris's infidelity as the reason. Then, ten years later, E News reported that they had been seen together at Coachella, chatting and laughing, alluding to a possible reconciliation. Ammika Harris (2015–2023)
Ammika Harris
Ammika Harris/Facebook
Model Ammika Harris began dating Chris in 2015, following his breakup from Tran. Their relationship remained relatively private, with few public appearances together, making it unclear exactly whether they were still together or not throughout their pairing. Then, in November 2019, they welcomed their son, Aeko Catori Brown, Chris Brown's second child. As of early 2024, reports suggest that while they maintain a close co-parenting relationship, but they are not romantically involved. Read More Tanmay Bhat On Creativity In Advertising
Diamond Brown/X
Chris Brown's third baby mama, Diamond Brown, was first linked to the singer in 2019, right around the time he welcomed his son with Ammika Harris. Diamond revealed she was pregnant in 2021, sharing a picture of her bump on Instagram with the caption: 'Just when you think you know love, something little comes along to remind you just how big it really is.'
She welcomed her daughter with Chris Brown, Lovely, in January 2022. In another Instagram post, she wrote: 'The princess is here! Lovely Symphani Brown🤎. My sweet babygirl, it's been a whole day you've been in the world and have already shown me the true meaning of life. I promise to love and protect you always. Forever yours, mommy.'
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