A Timeline of Rihanna & Drake’s Complicated Relationship

When Drake stood before the crowd at the 2016 MTV Video Music Awards, he began his speech by talking about the first time he ever met Rihanna. Rihanna was shooting the music video for “Pon De Replay” at a restaurant in Toronto and was introduced to Drake, who “played background music at the restaurant as people ate their dinner.” History has a way of repeating itself because the same director, Director X, who worked on Rihanna’s “Pon De Replay” video, also directed Drake and Rihanna’s “Work” video years later.

Shortly after Rihanna’s very public split from Chris Brown in 2009 after Brown’s assault of the singer, Page Six reported that Drake and Rihanna were spotted at Lucky Strike in New York City. Sources told the outlet that Rihanna was “making out with him all night.” 

Rihanna stopped by Angie Martinez’s radio show to discuss her headline-grabbing breakup with Chris Brown and address the rumors that she was dating then-90210 star Tristan Wilds and Drake. Speaking to Martinez, Rih shut down the rumors and revealed that she likes “hot and older” men and insisted that she and Drake were “still friends.” Martinez continued to press Rihanna about a possible romantic relationship brewing between the two artists, but Rihanna continued to deny there ever being a romance.

While Rihanna believed her relationship with Drake was strictly platonic, Drake seemed to have believed otherwise. In his Thank Me Later cut “Fireworks,” Drake comes to the realization that his feelings for her were far stronger than her feelings for him. “I could tell it wasn’t love, I just thought you’d f— 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.”

At one point in the verse, Drake implies that their relationship started heading downhill because Rihanna believed he was using her for clout. “Now all of a sudden, these gossip blogs want to cover me,” he raps. “And you making it seem that it happened that way because of me.”

In an interview with The New York Times, Drake admitted that he felt used by Rihanna. “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.’” 

However, Drake addressed his NYT interview in another interview with MTV News because he didn’t want it to come off “negative.”

“I’m at one of the greatest places in my life — 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,” he said, adding that Rihanna is an “overwhelming and incredible person.”

Drake and Rihanna seemingly put any differences aside when they joined forces for Rih’s infectious “What’s My Name?,” which soared to No. 1 on the Billboard Hot 100. In the video for “What’s My Name?” Rihanna and Drake are seen flirting in a local grocery store then cozying up in an apartment, reigniting rumors of a romantic relationship.

As “What’s My Name?” started heating up the charts, the connection between the two seemingly grew stronger. Rihanna performed the Drake-assisted hit at the 2011 Grammy Awards and seductively danced on the rapper as she sang, “Not everybody knows how to work my body/ Knows how to make me want it/ But boy you stay up on it.” Shortly after the Grammys performance, Rihanna and Drake gave another steamy performance of “What’s My Name?” at the NBA All-Star Game halftime show.

With a star collaboration with Rihanna under his belt, Drake was constantly reminded of her in his interviews. Drizzy opened up to ELLE about the inspiration behind “Fireworks” and admitted that he was “hurt” because he didn’t expect his relationship with Rihanna to go down like that. “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.”

The tandem’s “Take Care” team-up wasn’t as steamy as “What’s My Name?,” but that didn’t stop the rumors from swirling. In April 2012, Drizzy released the visuals for “Take Care,” in which the duo are seen hugging and caressing each other throughout the video.

TMZ reported that Drake and Chris Brown were involved in a scuffle at an NYC nightclub. According to the initial report, the men began yelling at each other and, eventually, a bottle was thrown, but Drake later denied being involved in the fight.

Rihanna apparently wasn’t feeling Drake during the 2012 MTV VMAs. When Drake won an award for best hip-hop video, the crowd erupted with praise, but Rihanna remained unbothered and instead whispered something to her best friend Melissa that many believed was an insult to Drake.

Drake and Chris Brown’s rumored beef didn’t seem to be dying down and Drake added fuel to the fire when he sat down with Elliott Wilson for the Keep It Thoro podcast. “Don’t ask me sh– about that man when I come up there, and leave that man alone. Stop preying on his insecurities, man,” Drake told Wilson. “His insecurities are the fact that I make better music than him, that I’m more popping than him and that at one point in life, the woman that he loves fell into my lap. I did what a real n—a would do and treated her with respect.”

When Drake paid Ellen DeGeneres a visit, Ellen persuaded the rapper to play a game where he opened up about the women he’s dated. Rihanna was the first picture and Drizzy had nothing but good things to say about the songstress. “Yeah, great girl. We had our moment and [I’ll] always support and have love for her.”

Even though they weren’t together, Drake still considered Rihanna his dream girl. “She’s the ultimate fantasy,” he said to Rolling Stone. “I mean, I think about it. Like, ‘Man, that would be good.’ We have fun together, she’s cool and sh–. But we’re just friends. That’s my dog for life.”

Despite constantly denying a romantic relationship, paparazzi spotted Rih and Drizzy out in London holding hands and getting into a car together. 

Sorry, Drake: According to Rihanna’s Vanity Fair interview, the singer said her last “official” boyfriend was Chris Brown.

It took the world a long time to recover from the glorious video Rihanna and Drake unleashed for their PARTYNEXTDOOR-written “Work” collaboration, mainly because the song stayed atop the Hot 100 for nine weeks.

Following the steamy video for “Work,” Rihanna tells Ellen that she’s still single. But the pair’s sultry dancing while performing “Work” at the 2016 Brit Awards and Rih’s Anti tour stop in Toronto keep the rumors of their rumored relationship alive and well.

The lyrics of “Too Good” suggest the song could be about Rihanna even though she’s featured on the track. “I’m too good to you, I’m way too good to you/ You take my love for granted/ I just don’t understand it.”

Ahead of presenting Rihanna with the MTV Video Vanguard Award, Drake surprised Rih with a billboard congratulating her on her award. She posted the image of the billboard on Instagram, writing, “When he extra ?–!!!”

Once again, Drake professed his love for Rihanna and reminisced about meeting the singer back when she was shooting the video for “Pon De Replay.”

“We love the videos, which change their artistic vision from year to year,” he said. “But most of all, we love the woman who hasn’t changed since day one. … 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.”

Sparks apparently started to fly after Drake’s speech, as AubRih were spotted out after the VMAs. And then they kissed onstage during Drake’s Miami concert.

“It’s somebody’s birthday today — somebody I have a lot of love for and a lot of respect for,” Drake told the crowd. As fans clapped and screamed, Drake continued, saying, “So, instead of singing ‘Happy birthday,’ though, we just going to do this in Dublin. Instead of singing ‘Happy Birthday,’ we’re gonna set it off just like this…” Drake then performed “Work.”

Drake and Rih’s romance seemingly died down to the point where it was awkward for them to be in a room together. The pair ended up at a kid’s birthday party together months after Drake was rumored to be dating Jennifer Lopez. In a video, Drake is seated on a chair while Rih is seen playing with some of the kids.

In an interview with Vogue, Rihanna briefly spoke about her relationship with Drake. Vogue writer Chioma Nnadi said Rih “winced” when Drake’s name was brought up. “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,” Rih said. Rihanna was asked about the current status of her friendship with the 6 God, to which she responded, “We don’t have a friendship now, but we’re not enemies either. It is what it is.”

When Drake released For All the Dogs on Oct. 6, fans started dissecting the lyrics and found possible references to Rihanna and her relationship with A$AP Rocky. In the “Fear of Heights” intro, Drake repeatedly says the word “Anti,” aka the title of Rih’s Billboard 200 No. 1 2016 album. Then, after lamenting how people “make it sound like [he’s] still hung up on” his ex, Drake goes on to seemingly diss Rocky with “That man, he still with you, he can’t leave you/ Y’all go on vacation, I bet it’s Antilles.” (Barbados — Rihanna’s home country and frequent vacation spot — is located in Lesser Antilles in the Caribbean.)

On “Virginia Beach,” Drake spits, “Drawin’ conclusions like you got a Parsons degree or somethin’/ I coulda treated you better, that’s crazy.” Rihanna has an honorary degree from the Parsons School of Design.

On “Another Late Night,” Drake seems to take aim again at A$AP Rocky. “I ain’t Pretty Flacko,” he raps, nodding to Rocky’s nickname, “Bi— this sh– get really Rocky.”