Drake and Rihanna's Long and Complicated Romance: A Timeline

When Drake confessed his longtime love for Rihanna on stage at the VMAs in August, it was a gratifying moment for many fans. The two were always close, but rumors of their on-again, off-again romance followed both of their careers for years. From getting spotted kissing in 2009 to collaborating together on tracks like "What's My Name?," "Take Care," and "Work," to getting scandalous onstage during Drake's "Summer Sixteen" tour, the two have always had something special. The more recent news that the couple may—once again—be going their separate ways had pretty much the opposite effect, with fans lamenting the rumored end to their storybook romance. Amid the swirling, Complex decided to put together a definitive timeline charting their relationship. 

After laughing about rumors that she was engaged to Drake, Rihanna says “No, me and Drake are friends… We’ve hung out a few times.”

On his Thank Me Later track "Fireworks," Drake addresses his brief romance with Rihanna. "I'm just such a gentleman, you should give it up for me/Look at how I'm placing all my napkins and my cutlery/I can 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/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," he raps. 

Although it sounds like there's some hard feelings between the two, they still get close in the video for Rihanna's Loud single, "What's My Name?"

After things quiet down between them for a minute, Drake pops back up with a sly reference to her on Rick Ross' "Made Men." "One of my baddest women ever, I call her Rihanna/But that's because her name is Rihanna," he raps.

When pressed about their relationship during an interview with British radio personality Max, Drake opens up. “I think we have a connection that’s established for life, and that is that I’ll love her and support her unconditionally, and I like to think that she thinks the same way." When Max asks Drake if he "fancies her," he says yes. “Do I fancy her? Of course, I mean who wouldn’t? Look at her, she’s stunning... It’s one of those things, that it’s a maybe one day, maybe not.”

Another collaboration, another steamy video.

Major drama breaks out in Manhattan after Drake and Chris Brown get into a brawl at W.i.P nightclub. Although it's not immediately clear what caused it—the two had been shading each other for a while—Drake later says that the fight is about Rihanna. "At one point in life, the woman he loves fell into my lap. I did what a real nigga would do and treated her with respect so she's not up there talking down on me." 

This one needs no explanation.

Ellen DeGeneres forces Drake to play a very awkward game in which he has to describe his relationship with a series of women. First up: Rihanna, who he talks about in the past tense. "Great girl, we had our moment and I'll always support and have love for her." He went on to say "I'm not into do-overs in any regard, which is an ironic thing to say."

Not only does "Days in the East" contain a sample of Rihanna's "Stay," but his lyrics seem to allude to him confessing his feelings towards her to Erykah Badu. "Remember one night I went to Erykah Badu house, she made tea for me/We talked about love and what life could really be for me/She said, 'When that shit is real, you just know'/And I was thinkin’ ’bout you, you already know."

After a long break from public appearances together, the two are spotted together at Coachella after Drake's set. Rumors kick back up that the two are seeing each other again.

In their first musical reunion since "Take Care," the pair make more magic. The song proves to be immensely popular, topping the Billboard Hot 100 chart for nine weeks. The "Work" video finds the two getting, in typical fashion, close.

Drake shows up at the Miami stop of Rihanna's ANTI world tour. The two run through "Work," grinding on each other, before Drake takes center stage for a rendition of "Jumpman." This is the first of several concert appearances together in 2016, including the Toronto, Canada and Manchester, England ANTI stops, as well as OVO Fest in Toronto. "Shout out to the most beautiful, talented woman I've ever seen," Drake says at the Manchester appearance. "She goes by the name of Rihanna...I'm gettin' my heart broken."

It's not exactly the most conventional way to say congratulations, but Drake buys Rihanna a billboard to celebrate her receiving the Video Vanguard Award at the 2016 VMAs. Rihanna puts a picture up on her Instagram. The caption? A heart.

In a sharp tux, Drake introduces Rihanna and presents her with her Video Vanguard Award at the 2016 VMAs. He gives a heartfelt speech before dropping this bomb: "She's someone I've been in love with since I was 22 years old," he says. Although some people think she curves him after not kissing him on stage, it turns out they actually did kiss. The two are later seen leaving the award show together and hitting up VMA after-parties.

If the VMA kiss wasn't enough, Rihanna shows up at the Miami stop of Drake's "Summer Sixteen" tour to perform "Bitch Better Have My Money." After she finishes, Drake kisses her. If Aubrih is ever going to happen, it seems like now is the time.

Despite "reports" of seemingly amazing romance between Drake and Rihanna, things may not be all that they seem. In an interview with TMZ, Drake's father, Dennis Graham, casts doubts. "There's no relationship, they're friends," he says to a TMZ cameraman. "They've been friends for years." Could the just be Dad playing coy, or is the media really reading too much into this?