The Work hitmaker and the Hotline Bling musician called time on their romance just months after they went public, and Chris - who dated the 28-year-old singer from 2007-2009, and briefly in 2013 - thinks their split is because Drake, 29, is a "boring mama's boy".
A source close to the 27-year-old singer told HollywoodLife.com: "[Chris Brown] knew it wouldn't last. No diss to Drake but he ain't man enough for Rihanna.
"He's not edgy and when you peel back all his sweet BS lines and charm you see the real Drake: a boring mama's boy."
And even though the Needed Me singer might have moved on from the Royalty musician, Chris hasn't given up on rekindling their relationship.
The spokesperson added: "[Chris] sent [Rihanna] a joking text telling her telling her she could lay on his chest if she needed a rock for support. She hit him back with 'lol.'
"That made Chris smile. [Rihanna]'s always giving him attitude and making him work it and he loves that about her."
Chris isn't the only former flame to get involved in the split either, as Drake's ex-fling Crystal Westbrooks took to Twitter to express her feelings on the news after it was reported that the One Dance hitmaker had already moved on from Rihanna and struck up a relationship with India Love - Crystal's sister.
She tweeted: "That awkward moment when she hops on your exs..... Nvm nvm nvm #iFeelLikeRayJ Well this is getting really awkward (sic)"
If that wasn't confusing enough, insiders admit there might be more to the new romance than meets the eye as India's ex-boyfriend, Cliff Dixon, was rumoured to have cheated on her with Rihanna.
A source said: "Drake could be hooking up with India Love now to p**s off Rihanna, which has clearly worked."
At the MTV Video Music Awards (VMAs) at Madison Square Garden in New York in August, Drake admitted he had been "in love" with Rihanna for years.
Presenting the 'S&M' hitmaker with the Michael Jackson Video Vanguard Award, he said of the brunette beauty: "She's someone I've been in love with since I was 22 years old. She's one of my best friends in the world. All my adult life, I've looked up to her, even though she's younger than me.
"She's a living, breathing legend in our industry, ladies and gentleman, the recipient of the Michael Jackson Vanguard Award for 2016, Rihanna."
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