A Timeline of Rihanna and Drake’s Complicated Relationship

Love at first sight … well, for Drake at least. It all began back in 2005, when the Toronto rapper encountered Rihanna. “The first time I met Robyn Fenty was 2005,” Drake revealed at the 2016 MTV VMAs. “She was shooting a music video at a restaurant called Avocado in Toronto. The song was ‘Pon de Replay.’ ? I was introduced to her as a kid who played background music at the restaurant as people ate their dinner. It’s hard to believe that was 11 years ? they know me as Drake and not the kid singing while you order pasta. But 11 years later, we still all know Rihanna as the one and only Rihanna.” Luckily for Drake, he got to know his crush a little better. (Photos: Vevo/WireImage)

Flash forward four years, when Drake finally landed his first kiss. At least, the first kiss we all knew about. Page Six ran an item about the Canadian crooner and Barbadian beauty locking lips at Lucky Strike in NYC. “She was drinking whiskey and apple juice and making out with him all night,” said a spy. “They were really cute together.” (Photos: Getty Images/FilmMagic)

A few months later, Rihanna firmly put Drake in the friend zone. During an interview with radio station Hot 97, the singer said she and Drake were just friends. “We weren’t really sure what it was,” she said. “We just went out ? my friends, his friends.” She (brutally) added, “I don’t even have his number ? I need somebody that’s hot … and older.” Ouch. (Photos: WireImage/FilmMagic)

After Rihanna brushed off their makeout session, the rapper was more eager than ever to talk about their relationship in his song “Fireworks.” Some choice lyrics include: “I could tell it wasn’t love, I just thought you’d f*** with me/Who could’ve predicted Lucky Strikes would have you stuck with me?/What happened between us that night it always seems to trouble me/Now all of a sudden these gossip sites wanna cover me/And you making it seem like it happened that way because of me/But I was curious and I never forget it, baby, what an experience/You could’ve been the one, but it wasn’t that serious.” (Photo: Corbis via Getty Images)

Drake talked to the New York Times and clarified his feelings about his one-night whatever with Rihanna. "I was a pawn,” he 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 told MTV that he didn’t mean that comment to be negative. “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 confessed. “She’s just such an overwhelming and incredible person ? she made me feel nervous. It just put me back to the Acura in Toronto, feeling like Aubrey Graham, not Drake.” (Photos: FilmMagic/Getty Images)

Rihanna was spotted at Drake’s post-concert party at Greenhouse in New York City. But what did it mean?! (Photo: WireImage)

Rihanna and Drake teamed up for their first of many collaborations and megahits. They released “What’s My Name?” and went on to deliver some steamy performances, including one at the 2011 Grammy Awards. (Photo: Vevo)

One year later, the two friends appeared to be keeping things strictly professional. Drake opened up about some of the prior comments he made about Ri: “At the time it hurt, but she didn’t mean to. I’ll never put that on her,” he told Elle. “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.” Several months later, the duo joined forces again for Drake’s song “Take Care.”(Photo: Vevo)

Rihanna’s ex-boyfriend Chris Brown and Drake got into physical altercation at a club in NYC, reportedly over the singer, who wanted no part of that quarrel. “There’s no proof of that being for my love,” she told GQ. “That’s my answer to that question.” Fortunately, Drake loves to talk about his feelings, and confirmed the brawl was over Rihanna. “It’s embarrassing, the amount of media coverage,” he later told GQ. “Two rappers fighting over the woman.” (Photos: Getty Images/WireImage/FilmMagic)

Poor Drake. Nearly three years after Brown assaulted Rihanna, the exes got back together. But it didn’t last long. They split nine months later. (Photo: Getty Images)

Would the second time be the charm? Rihanna was spotted partying with Drake after one of her concerts in Los Angeles. Of course, rumors began to fly that the duo was on again. (Photos: FilmMagic)

A few months later, Drake and Rihanna spent the most romantic day of the year partying together at Hooray Henry’s in West Hollywood. Around the same time, Drake told Rolling Stone that Rihanna was his “ultimate fantasy.” He added, "I mean, I think about it. Like, ‘Man, that would be good.’” Shortly after, it looked as if his fantasy was about to become a reality when Rihanna popped up at his concert in Paris. (Photo: Splash News)

Well, what do we have here? For the first time, Rihanna and Drake seemed to confirm their romance when they were caught holding hands in London. (Photo: AKM-GSI)

The lovebirds were still going strong when they took their love back to the States and were photographed hugging at a Clippers game in L.A. (Photo: Splash News)

Maybe we spoke too soon. As Rihanna and Drake’s romance seemed to fizzle out again, the Canadian rapper and Chris Brown squashed their beef when they appeared in an ESPYs skit together. “They were actually really friendly with each other,” a source told Us Weekly, adding that it “didn’t seem like there was any tension at all.” (Photo: ESPY Awards)

It became clear that Drake and RiRi were dunzo when a photo of Rihanna flashed across the stage backdrop with the number “666” during Drake’s performance at OVO Fest. (Photo: TMZ)

One year later, we spied Drake sporting what appeared to be a tattoo of Rihanna. Twitter confirmed the ink was definitely of his new/old love when a fan posted a photo from Fring’s (a Toronto restaurant whose name was inspired by Drake), where there’s a photo of Rihanna that looks a lot like that picture on his arm. (Photo: Instagram)

Drake and Rihanna got together (musically) again for her song “Work.” However, Rihanna clarified her relationship status when talking with Ellen DeGeneres. “I’m single right now and it’s not that I’m like, ‘Oh, pro-single, yes, I hate men!’ I just think I have so much on my plate that I can’t even find the time to entertain a steady relationship or anything serious,” she said. “Or even a text.” (Photo: Vevo)

Drake popped up in Miami for Rihanna’s 2016 “Anti World Tour,” where they demonstrated that they clearly had chemistry during a performance of “Work.” This marked the first of many surprise appearances he would make for his main squeeze along the way. (Photo: Youtube)

Drake followed Rihanna across the pond to London, but they weren’t only hanging out on the stage. The duo hit the town together and reports surfaced they were definitely dating again. “He still loves her and never stopped. Rihanna is the one that’s been not wanting to settle down in the past,” a source told E! News. “They are having fun spending time with each other. Their music together got them close again.” (Photo: Splash News)

Drake deserved some serious boyfriend props when he rented a billboard congratulating Rihanna ahead of accepting the Vanguard Award at the VMAs. “When he extra [heart] !!!” Rihanna captioned a photo of the sign. (Photo: Instagram)

The rapper introduced his lady love on stage at the 2016 VMAs and didn’t hold back his feelings. “She’s someone I’ve been in love with since I was 22 years old,” he gushed. “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.” Rihanna sneakily let him give her a kiss before she accepted the award (even though we all thought he got burned at first). (Photo: FilmMagic)

Drake and Rihanna followed up the nondiss kiss with a dinner date in NYC ? where RiRi wore Drake’s tuxedo shirt from the night before! The couple then jetted off to Miami. At an afterparty for his concert, witnesses told Us Weekly the duo “were making out and full-on kissing.” A source also told People they “danced, kissed, and acted really coupley.” (Photo: INFphoto)

While rumors swirled this week that Drake was hooking up with model India Love, and that he and Rihanna had parted ways, a source told People that Drake and Rihanna aren’t exclusive: “It’s an open thing.“ Stay tuned… (Photos: Splash News)