Chris Brown’s latest TikTok activity might have fans remembering one thing: he very clearly has a type.
Earlier this week, Brown popped up in the comments under a woman’s TikTok post where she said someone had complimented her by saying she looked like Karrueche Tran, Brown’s former longtime girlfriend. The singer responded with a simple “😏”, but the comment was enough to send us down a familiar rabbit hole: the women he has dated over the years and the ‘coincidental’ similarities between them.
Rihanna and the early relationship years
Chris Brown’s first widely known relationship began in 2007 when he started dating Rihanna. At the time both artists were rising stars and quickly became one of pop music’s most visible young couples.
The relationship ended in 2009 after Brown assaulted Rihanna the night before the Grammy Awards, a case that led to felony assault charges and probation. The two briefly reconciled in 2012 and even collaborated musically before splitting again the following year.
Karrueche Tran and the on-off era
By 2011, Brown had begun dating model and actress Karrueche Tran. Their relationship lasted several years on and off and became one of the most public chapters of Brown’s personal life.
The relationship ended in 2015 after Tran learned that Brown had fathered a child with another woman. Two years later, in 2017, Tran obtained a five-year restraining order against the singer following allegations of harassment and threats.
Brown’s children and their mothers
Brown is also a father to three children with three different women.
His first child, Royalty Brown, was born in 2014 to Nia Guzman, a model and former partner. News of Royalty’s birth became the reason his relationship with Karrueche Tran ended.
In 2019, Brown welcomed his second child, Aeko Catori Brown, with model Ammika Harris, who was romantically linked to the singer for several years.
Brown’s third child, Lovely Symphani Brown, was born in 2022 to model Diamond Brown.
Other women linked to Brown
Outside of those relationships, Brown has been linked to several other women over the years. Among them are Draya Michele, who was rumored to be involved with him briefly in the early 2010s.
Brown himself has also spoken about his relationship status in recent years. During an appearance on Kai Cenat’s Mafiathon 2 stream in November 2024, the singer was asked whether he was currently in a relationship. Brown responded candidly that he was seeing more than one person.
“Me? Am I in a relationship? I’m in multiple,” Brown said during the stream.
When Cenat followed up asking if that meant more than one girlfriend, Brown replied, “Something like that,” adding that honesty was the key to managing it.
“Just keep it 100. Just be honest.”
Internet sleuths, however, seemed to have tracked down who one of these potential partners are. The 25-year-old model Jade Wallace has been linked to Brown since December 2024, first spotted with him at an after-party in South Africa.
@samrakoba 👀😂 @chrisbrownofficial #chrisbrown #southafrica #breezybowl #johannesburg
By August 2025 she was posting with his daughter Royalty, and by Paris Fashion Week in January 2026 fans were convinced she was more than just a plus one — with many pointing to a visible bump and the fact that she turned down drinks at an afterparty as signs she could be expecting.
His ex Diamond Brown seemingly confirmed it weeks later, posting "worry about your new baby on the way" during a very public Instagram fallout between the two women. Neither Brown nor Wallace has confirmed the pregnancy.
Regardless, looking back at the timeline, it’s hard not to notice the physical similarities between many of the women Brown has dated — and judging by the internet’s reaction every time a new name pops up, we’re clearly not the only ones who see it.