Drake & Rihanna's Relationship Timeline Is An Emotional Rollercoaster

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. In Elite Daily’s new series, It’s Complicated, we’re highlighting the biggest celebrity “feuds” that took over Hollywood and dominated our Sunday brunches for weeks on end. We’ll take a deep dive into the lives and social media feeds of our favorite stars and dissect what happened in front of the camera, what went down behind the scenes, and everything you might have missed in between.

Rihanna and Drake have a long history together. Rihanna came up in music before the rapper, but once they started collaborating, their work together (and basically every interaction) had pretty much everyone convinced they were a thing. 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?

It's a long, complicated history that all started back in...

2005: Drake and Rihanna meet.

Drake shared the story of how he and Rihanna met during his infamous speech at the 2016 MTV Video Music Awards where he presented Rihanna with the Video Vanguard Award. He said Rihanna was filming her "Pon de Replay" music video in the restaurant he "played background music at ... as people ate their dinner." It's not clear if Drake meant he was a DJ at that restaurant when he first met Rihanna or if he was there at the same time by chance, but suffice it to say, Drake hadn't made his come-up when the two met.

Drake said in that same VMAs speech that he'd been in love with Rihanna since he was 22. He was 19 and she was 17 in 2005, so it looks like things didn't heat up between these two for a couple more years.

2009: They have their first "date" after Rihanna and Chris Brown break up.

Long before there were Drake and RiRi 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.

In May 2009, a now-single RiRi was reportedly seen partying at Lucky Strike in New York City with Drake. Page Six reported that the two were seen "making out all night."

Despite speculation the pair were dating, Rihanna clarified that she and Drake were "still friends" in an interview with Angie Martinez in November 2009.

2010: Drake makes his first mention of Rihanna in his lyrics, and they collaborate on their first single.

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 Thank Me Later track, "Fireworks," featuring Alicia Keys, Drake seemingly rapped about Rihanna and their night at Lucky Strike.

In the song's second verse, Drake raps,

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? / It always seems to trouble me / Now all of a sudden, these gossip blogs want to cover me / And you making it seem that it happened that way because of me

It's hard to imagine that Lucky Strike line being about anything other than their rumored night together at the NYC club in 2009.

Drake clearly wasn't entirely happy about how their almost-thing fizzled out. The same month "Fireworks" came out, Drake gave the world no room to doubt how he felt about it all. He told the New York Times he felt like Rihanna's "pawn," and that she beat him at his own game.

"I was a pawn,” Drake said. “You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, 'Wow, this feels terrible.'”

He later backtracked a bit on that comment in an interview with MTV News, saying he was bitter about how things worked out with her because, as a result of his musical success, he wasn't used to feeling small.

"'I'm at one of the greatest places in my life," he said. "I'm on top of the world. I'm extremely confident, so it's very rare that anybody, let alone a woman that I like, makes me feel nervous or makes me feel small." Been there.

If it seems like Rihanna hasn't had much say in this narrative, it's because while Drake was public about their almost-thing, Rihanna was largely tight-lipped in comparison. She still made music with him though, as we all know.

So, things were seemingly platonic from that point on, until "What's My Name" came out in October 2010.

The song was... sexual. Their performance of it at the Grammys in February 2011 was... sexual.

Queue the dating rumors again.

2011: Drake admits "Fireworks" was about Rihanna, they release "Take Care" later that year.

Although their almost-thing was long over (despite what their sexy collabs would have you think), Drake confirmed to Elle in 2011 that "Fireworks" is about Rihanna.

"At the time it hurt, but she didn't mean to. I'll never put that on her," he said. "I was hurt because I started to slowly realize what it was. I guess I thought it was more. That was the first girl with any fame that paid me any mind."

They released "Take Care" the same year — a track where Drake talks about taking care of a woman who was mistreated by a man in the past. It's not hard to imagine how this song could be inspired by Rihanna and Chris Brown's tumultuous relationship.

2012: Rihanna seemingly shades Drake at the VMAs.

Tensions between RiRi and Drake seemed to be high in August 2012 at the MTV VMAs. Drake won Best Hip-Hop Video that year and Rihanna won Video of the Year. A friend would be excited about his win, but viewers were convinced that Rihanna called him an asshole as he walked past her to the stage. Maybe she called him an asshole because he wouldn't stop talking about her in interviews? I'm just sayin'!

2013: Drake brings up Rihanna while talking about his public beef with Brown.

Drake and Brown were both public about their rivalry for years. In an April 2013 interview with Elliott Wilson on the Keep It Thoro internet radio show, Drake claimed that the rivalry began because "the woman that [Brown] loves fell into [his] lap." That woman would be Rihanna, who, again, didn't talk about Drake publicly. Like, at all. (Flash-forward to 2019, and Drake and Brown have just released a single and music video called "No Guidance" together. My my, how the times have changed.)

2014: Their friendship is back on.

Drake told Rolling Stone in a February interview that he and Rihanna were good friends, but he also said she was still his dream woman.

"She's the ultimate fantasy," he said. "I mean, I think about it. Like, 'Man, that would be good.' We have fun together, she's cool and sh*t. But we're just friends. That's my dog for life."

Maybe calling her his dream girl worked this time around, seeing as in March 2014, the two were seen holding hands in London.

2015: Rihanna clarifies that her last official boyfriend was Brown.

In what must have been a brutal blow for Drizzy's ego, Rihanna told Vanity Fair in a 2015 interview the last person she was in a relationship with was Chris Brown. Yikes. Guess that "date" in London didn't go well. Or maybe she was meeting up with him to tell him to stop talking about her in interviews *insert upside-down smiley emoji here*.

2016: "Work" comes out, and the impossible seems to have happened: Drake and Rihanna seemingly start dating.

Things between Rihanna and Drake seemed quiet for a while, and then they dropped "Work" in February. The steamy music video for that song was then followed by more steamy live performances.

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! News. "Rihanna is the one that's been not wanting to settle down in the past. They are having fun spending time with each other. 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. "She goes by the name of Rihanna...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 ❤!!!" as the caption. Um, yeah. That billboard looks like something you do for your girlfriend (when you're rich as hell), and that caption is something you say about your man.

Then, Drake gave that speech about RiRi 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.

In September 2016, the two seemingly got matching tattoos of a camouflage shark.

2016: Rihanna and Drake break up.

In October 2016, E! News reported that Rihanna and Drake broke up. 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.

2018: Drake and Rihanna's friendship is no more.

Rihanna talked about Drake (and that Video Vanguard moment) in an interview with Vogue in May of 2018, marking one of the few times she ever spoke about him in interviews.

"Waiting through that speech was probably the most uncomfortable part. 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.

When she was asked what their current dynamic was, she said, “We don’t have a friendship now, but we’re not enemies either. It is what it is.” They had unfollowed each other on Instagram at this point, so that tracks.

Even Drake (who was still talking about her in interviews... this train will never stop) admitted that he and Rihanna were done. When speaking with LeBron James on The Shop in October 2018, he said his "fairy tale life" used to be settling down and having kids with Rihanna.

Clearly, that's not how things panned out. Take care, Drake and RiRi.