A Timeline of Rihanna & Drake's Complicated Relationship

Kevin Mazur/WireImage
Rihanna and Drake pose onstage during the 2016 MTV Video Music Awards at Madison Square Garden on Aug. 28, 2016 in New York City. 

From steamy collaborations to public outings, Rihanna and Drake have toyed with fans’ emotions for many years, constantly sparking speculation as to what the status of the pair’s mysterious relationship or friendship is.

The term “just friends” has come up often when Rihanna and Drake have been coaxed into discussing their relationship. But in a new profile for Vogue, Rihanna shattered the hearts of those pining for the “Work” collaborators to be together because, according to the singer, they’re no longer friends.

Nearly two years ago, Drake stood up on the 2016 MTV Video Music Awards stage to present Rihanna with the Video Vanguard Award and professed his love for the Anti singer for all the world to hear. So where did it all go wrong? We may never know.

Below, Billboard takes a look back at Rihanna and Drake’s history.

Drake and Rihanna's First Encounter - 2005

When Drake stood before the crowd at the 2016 MTV Video Music Awards, he began his speech by speaking 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.

First Date - May 2009

​Shortly after Rihanna's very public and calamitous 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 Says She and Drake Are “Still Friends” - November 2009

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. 

Drake Realizes Rihanna May Not be That Into Him - June 2010

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 fuck 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.”

Drizzy Believes Rihanna Used Him - June 2010

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."

The Pair Reunite for "What's My Name" - October 2010

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. 

Rihanna Dances on Drake During Grammys Performance - February 2011

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.

 

AubRih is Real since day 1 ---- #AubRih #Drake #Drizzy #Rihanna #TBT

A post shared by Drake's #1 Fan (@aboodovo) on

 

Drake Admits He Was "Hurt" by Rihanna So He Made "Fireworks" - October 2011

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."

Drake & Rihanna Team Up Again for "Take Care" - November 2011 

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.

Drake & Chris Brown Reportedly Fight Over Rihanna in a Club - June 2012

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 Didn't Clap for Drake's MTV VMA Win - September 2012

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 Addresses Rumored Chris Brown Beef During a Radio Interview - April 2013

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 shit 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."

Drake Tells Ellen He & Rihanna "Had Their Moment" - September 2013

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." 

Drizzy Continues to Praise Rihanna - February 2014

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 shit. But we're just friends. That's my dog for life."

Rihanna & Drake Have a Date Night in London - March 2014

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

Rihanna Denies Ever Dating Drake - November 2015

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

Rihanna & Drake "Work" It Out - February 2016 

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 Billboard 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.

AubRih Join Forces for "Too Good" From Drake's Views Album - July 2016

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."

Drake Surprises Rihanna With a Billboard -- August 2016

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 ❤--!!!"

 

When he extra ❤--!!!

A post shared by badgalriri (@badgalriri) on

 

Drake Delivers a Heartfelt Speech About Rihanna at the MTV VMAs - August 2016

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... 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.

 

Work. Rihanna ft Drake. En vivo -- #rihanna #drake

A post shared by Miguel Angel Pylik Potarsky (@miguelangelpylik) on

 

Drake Gives Rihanna a Birthday Shout-Out During a Concert - February 2017 

It's somebody's birthday today -- somebody I have a lot of love for and a lot of respect for," he told the crowd. As the crowd 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..." and performed "Work."

Drake & Rih Have an Awkward Run-In at a Birthday Party - April 2017

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 months after Drake was rumored to be dating Jennifer Lopez. In the video, Drake is seated on a chair while Rih is seen playing with some of the kids.

 

Rihanna Reveals She & Drake Aren't Friends - May 2018 

In a new 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.”