He is constantly breaking up and making up with his girlfriend, Karrueche Tran.
But it seems like the couple are off once again after the pair shared a series of telling tweets and photographs.
According to Complex magazine, Chris Brown confirmed his new single status at the Cali Christmas concert on Friday night.
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Can't make up thier minds: It seems like Chris Brown and Karrueche Tran have called it quits once again
Twitter user Blogxilla tweeted that the singer reportedly addressed the crowd asking: ‘how many single ladies out there tonight? I'm single too! F*** that b****!’
And Karrueche appears to hint that she chose to end the relationship as she tweeted: ‘N****s be in they feelings when you break up with them Chris added more stoke to the fire as he shared a picture of himself partying with Khloe Kardashian and her half-sisters Kendall and Kylie Jenner.
Kendall and the rapper – who have been pictured together at over parties – once again seemed close as the model is seen perched on his lap for the shot.
Friendly position: Chris added more stoke to the fire as he shared a picture of himself partying with Khloe Kardashian and her half-sisters Kendall and Kylie Jenner
MailOnline has contacted representatives of Chris Brown for comment.
Not doubt set to make Karrueche's blood boil more was that the Keeping Up With The Kardashians stars were dressed to impress.
Kendall stepped out in a pair of leather pants, a low cut T-shirt and lace bunny ears complete with veil.
Oh dear: According to Complex magazine, Chris Brown confirmed his new single status at the Cali Christmas concert on Friday night
Break up: Karrueche appears to hint that she chose to end the relationship as she tweeted, 'N****s be in they feelings when you break up with them lol'
Khloe meanwhile donned a pair of tight black jeans with thigh high boots and a flannelette bomber jacket and Kylie wore skinny jeans with a cropped leather jacket.
Chris and his girlfriend had just knocked down split rumours last month after Karrueche tweeted: ‘Looks like I'm a single lady again’.
As fans reacted she then added: ‘I was talking about the show Single Ladies.. I just came back from shooting an episode lol gee wiz’.
Not helping: Not doubt set to make Karrueche's blood boil more was that the Keeping Up With The Kardashians stars were dressed to impress
Dress ups: Kendall stepped out in a pair of lace bunny ears complete with veil for the concert
Both Chris and Karrueche have been on and off for four years and in that time Chris managed rekindle romance with Rihanna before returning to Karrueche.
During a recent interview on Hot 97's Ebro In The Morning radio show, the American artist spoke about his relationship with the Karrueche.
‘It's been almost five years. She's straight. I dig her man. She's dope...,’ he explained. ‘I feel like, especially being in this industry, you just need somebody that understands you; who understands who you are personally except for your name.
‘Me and her have a real connection, like best friends on top of our intimacy. At the end of the day, me and her have a great relationship. We're best friends.’
Just kidding: The pair just knocked down split rumours last month after Karrueche shared a misleading tweet
Happier times: Both Chris and Karrueche have been on and off for four years and in that time Chris managed rekindle romance with Rihanna before returning to Karrueche
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