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No matter how many times she insisted they were just friends, Drake still carried a torch for Rihanna until 2010, when his lyrics started to reflect his doubts that she cared for him in the same way he cared for her.On his June 2010 I could tell it wasn't love, I just thought you'd f*ck with me/ Who could of predicted Lucky Strike would have you stuck with me/ Damn, I kept my wits about me luckily/ What happened between us that night?Long before there were Drake and Ri Ri dating rumors, Rihanna dated Chris Brown.Rihanna and Brown went public with their relationship in 2008, but Brown physically assaulted Rihanna in February 2009, leading to their breakup.Drake and Rihanna's relationship timeline is a long one, spanning from the early days when the two collabed on songs with steamy, emotional music videos, to now, when their friendship — according to Rihanna herself — is nonexistent.So how did these two — who had a close friendship for over 10 years and maybe dated at two different points during that friendship — end up not speaking to each other anymore?

I don’t like too many compliments; I don’t like to be put on blast," she said of his speech where he professed his love.Celebrity relationships and friendships are a rare breed.These famous faces have their lives played out in front of the masses, whether it’s the good, the bad, or the straight-up shady.Around this time, anonymous sources close to the two started telling outlets that Drake and Rihanna were finally dating, saying it was their music that brought them together."He still loves her and never stopped," a source told E! "Rihanna is the one that's been not wanting to settle down in the past. Their music together got them close again."The rumors seemed to be legit, considering Drake's shoutout to Rihanna after performing "Work" with her live at her concert in Manchester on June 29."Shoutout to the most beautiful, talented woman I've ever seen," he said. I'm gettin' my heart broken."Rihanna was then announced as the 2016 MTV Video Vanguard Award recipient and when the news was announced, Drake surprised her with a massive billboard that read, "Congratulations to Rihanna from Drake and Everyone at Ovo."The dating rumors seemed all the more legit when Rihanna posted a photo of the billboard and wrote "When he extra ❤!!! Then, Drake gave that speech about Ri Ri as part of her Video Vanguard Award moment that I mentioned earlier."She's someone...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," he said in the August 2016 speech. An anonymous source told the outlet they were seeing other people, saying, "They still love each other, but their schedules have gotten in the way.""They are still in each other's lives," the source noted.

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