Chris Brown’s Romantic History: From Rihanna To Ammika Harris & To Diamond Brown

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Since catapulting into the spotlight at such a young age, Chris Brown‘s personal life has been front and center. The young R&B singer’s love life has really taken center stage. From scrutiny over his relationship with Rihanna to welcoming three children all from different relationships, Chris’s personal life has become a topic of conversation amongst his devoted fans. Now, we’re taking a look back at the women he dated.

Rihanna

Between 2007 and 2009, Chris was in a high-profile relationship with Rihanna. The two singer’s started out merely as friends in the mid-2000s before their platonic relationship blossomed into a romance. The couple’s romantic partnership was further scrutinized in February 2009, when Chris physically assaulted Rihanna following an argument that escalated into a physical altercation.

By June 2009, Chris pleaded guilty to a felony assault months after images of Rihanna’s beaten face surfaed. He was ordered to serve community labor, five years probation and submit to domestic violence counseling. Four years after the assault, Rihanna and Chris got back together in early 2013. By May 2013, however, the two went their separate ways.

Both Chris and Rihanna have spoken in detail about their relationship in the past, a romance that has become a pivotal point in Rihanna’s personal life and practically redefined Chris’s career trajectory. Rihanna, notably, opened up to Oprah Winfrey about their romance in 2012. “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,” she shared on the mogul’s Next Chapter series on OWN.

“I truly love him,” she concluded. “The main thing for me is that he is at peace. I’m not at peace if he’s a little unhappy or he’s still lonely. I care. It actually matters that he finds that peace.”

Karrueche Tran 

During his initial breakup with Rihanna, Chris began dating model Karrueche Tran in 2011. By October 2012, however, the two went their separate ways. After Chris’s rekindled relationship with Rihanna didn’t work out, he reunited with Karrueche. But the couple’s relationship became more and more troubled.

As the pair seemingly tried to rebuild their romance, circumstances became far more worrisome. Karrueche and Chris eventually split after news of Chris’s child with Nia Guzman became public in 2015. Even more startling, Karrueche alleged that Chris was threatening her with violence. She subsequently was granted a five-year restraining order from Chris in 2017.

Years after their split, Karrueche shared EXCLUSIVELY with HollywoodLife that her life was back on track. “It is amazing to think where I was four years ago to where I am now and it pushes me to want to do more and become better and the long term goal for me is acting and getting on the big screen,” she shared with HL in May 2019. “I feel like I am the rose that grew from concrete, it’s that little bud that starts and keeps growing and growing and you learn that the world is your oyster and you can continue to grow with staying focused and hard work!”

Nia Guzman

One of Chris’s least publicized relationships was with Nia Guzman. The two weren’t exactly together for very long, but during their time together they welcomed a daughter, seven-year-old Royalty Brown. Royalty was born in May 2014, but news of Chris’s firstborn didn’t become public until the singer learned that he was the father in 2015, when the singer had reunited with Karrueche.

Over the years, Chris and Nia’s co-parenting has been difficult. In 2018, the two had an intense legal squabble over child support for their little girl. But in the years since, the parents have seemingly reached an agreement. “Chris gets along great with Nia because they decided a long time ago to make things work for the sake of Royalty,” a source shared EXCLUSIVELY with HollywoodLife in March 2020. For the young father, Royalty is “the most important girl in his life and he is willing to do whatever it takes to show her how much her parents love her and that she sees how well they get along.”

Agnez Mo

Between 2017 and 2018, Chris was rumored to be linked to Agnez Mo. The two initially got cozy in September 2017. After they first met, flirty messages exchanged between the two piqued fans interest. By November 2017, Chris and Agnez really riled-up fans when photos of the pair snuggling in the recording studio went public. The last sighting of the two came in January 2018, when they were spotted on a cute date at Disneyland. The romance apparently didn’t last long, and the two singers subsequently went their separate ways.

Ammika Harris

Chris’s had a talked-about romance with Ammika Harris. Rumors about the two being an item swirled throughout 2019. But by late November of that year, fans knew that the one-time couple were definitely serious at one point during their romance. The two welcomed their son, Aeko, on November 20 of that year.

Since bringing their little boy into the world, Ammika and Chris’s lives have been completely upended by the COVID-19 pandemic, which hit just months after little Aeko’s birth. Ammika went back to Europe to continue her modeling work, bringing Aeko with her. Chris, however, remained in the United States. Fortunately he was able to reunite with Ammika and Aeko in London before the family went on a vacation to Tulum, Mexico, in November 2020.

As for where Chris and Ammika currently stand, a source shared EXCLUSIVELY with HL that the two are just figuring their status out. “Chris and Ammika haven’t put an official label on where things stand with them right now because they’re still trying to figure out what their next move is,” the source shared. “They know the love is there and they’ll always be in each other’s lives, obviously, but there are so many variables at this point and everything is still up in the air.”

Diamond Brown

Chris was first linked to Diamond Brown in June 2019, when he “liked” one of the young model’s IG posts while Ammika was pregnant with his son. Diamond had also attended the “Forever” singer’s 30th birthday party in May 2019. Diamond revealed she was pregnant in September 2021, and fans quickly surmised that Chris was the baby’s father. In the comments section of Diamond’s Nov. 24 Instagram post, one follower said, “baby breezy is almost here.” A different fan wrote, “Young CB coming soon,” while a third person tagged Chris and congratulated him in the comment section, sharing a baby bottle and teddy bear emoji.

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A post shared by Aeko💙 Royalty💗 and Lovely 🤍 (@aeko.royalty.lovely)

Diamond gave birth to a daughter, Lovely Brown, in January 2022. It wasn’t until April 2022, when Lovely was three months old, that Chris confirmed he was indeed the father of Diamond’s child. The superstar singer posted a photo of his baby girl to his Instagram Story and wrote several heart emojis. It marked the first time Chris publicly acknowledged the baby.