Rihanna and Drake: A Timeline of Their Maybe-Relationship (PHOTOS)
Rihanna and Drake: A Timeline of Their Maybe-Relationship (PHOTOS)
Credit: Kevin Winter/Getty Images    


Rihanna and Drake: A Timeline of Their Maybe-Relationship (PHOTOS)


We can hardly contain our excitement with the latest from the celebrity relationship rumor mill: Rihanna and Drake are maybe-probably back together, again!

As usual, neither singer's camp has confirmed or denied a relationship — seriously, these two could grow old together and we'd still only have the rumor mill to go on — but at the very least they appear to be happily hanging out again. Isn't that all any of us can hope for, anyway?

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Read on for a timeline of their relationship, from their first dates in 2009 to their frequent collaborations to their longtime friendship… and more.

2009-2010: Relationship Beginnings

May 18, 2009: The date where it all began! Drake, still relatively unknown, is spotted out with RiRi at Lucky Strike Lanes & Lounge in New York. A source tells Page Six, “She was drinking whiskey and apple juice and making out with him all night… They were really cute together.”

Drake is her first rumored beau after an especially terrible, violent breakup with Chris Brown earlier that year.

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June 15, 2009: RiRi and Drake are spotted together again, this time at an after-party for the film Year One. Once again, Page Six has a source with the scoop: “She and Drake were attached at the hip… They are definitely together, but really trying to be discreet.”

May 26, 2010: The Drake single "Fireworks," featuring Alicia Keys, is released. Remember how he and RiRi went to Lucky Strike Lanes? Check out these lyrics: "Who coulda predicted Lucky Strike would have you stuck with me? What happened between us that night, it always seems to trouble me." Yikes.

When asked about the song in the New York Times a couple of weeks later, Drake says he "was a pawn."

“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,” he admits. “I was like, wow, this feels terrible.”


2010-2012: What's My Name and Take Care

October 26, 2010: Drake is featured on Rihanna's super-sexy single "What's My Name," released in advance of her 2010 album Loud. "The only thing we have on is the radio," he croons. "Say my name, say my name, wear it out/It's getting hot, crack a window, air it out"? Ummph.

Rihanna, for the record, is dating baseball player Matt Kemp at the time.

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November 12, 2010: Rihanna and Drake cuddle up in the sexy-cute video for "What's My Name."

November 18, 2010: Rihanna denies breaking Drake's heart on Power 105.1's morning show. “I would definitely say, that was wrong, he doesn’t know what he’s talking about,” RiRi says.

She goes on to say that Drake's an ideal partner… in music. “We just became friends and we left it at that. We get along really well. Drake has a youthful thing about him and he is very melodic with the way he writes and I felt I needed someone like that for ‘What's My Name.'”

Rihanna and Drake: A Timeline of Their Maybe-Relationship (PHOTOS)
Credit: Jeff Gross/Getty Images    

February 13, 2011: With Rihanna no longer dating Matt Kemp, Drake and Rihanna's steamy performance of "What's My Name" at the 2011 Grammy awards raises tons of eyebrows — the pair's chemistry is still going strong. They'd reprise the performance for the 2011 NBA All-Star Game a week later.

October 2011: Although they're active collaborators at this point, Drizzy finally opens up about his and Rihanna's previous relationship in a 2011 interview with Elle. When asked if RiRi hurt him, he responds, "At the time it hurt, but she didn't mean to. I'll never put that on her. I was hurt because I started to slowly realize what it was. I guess I thought it was more."

He continues, "That was the first girl with any fame that paid me any mind. You spend days reading about this person in the magazines. All of a sudden you have this number-one song and you're at some birthday party and there she is. And you're just some naive kid from Toronto staying in some s—y-ass hotel who got invited to this party on a whim. That's just how it happened."

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November 15, 2011: Drake's second studio album, Take Care, is released — with a title track featuring RiRi about two damaged people beginning a relationship together. Everyone gets all shippy! The song breaks out as a single on February 21, 2012, and reaches number 7 on theBillboard Hot 100.

April 6, 2012: The intimate video for "Take Care" is released, featuring a shoulder-baring Rihanna cuddling up to Drake in a stark black and white. Their chemistry is intense, and we all wonder why this pair ever called it quits in the first place.

2012-2013: Chris Brown Love Triangle and the Infamous Nightclub Brawl

June 13-14, 2012: Things come to a head between Rihanna's two main dudes when Drake and Chris are both seated at the same nightclub… and chaos ensues. Reports are fuzzy, but witnesses tell TMZ both men and their entourages were sitting in the VIP section when they started yelling at each other. Eventually, reports say, the yelling escalates to shoving, and then a fight erupts after a bottle is thrown.

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Chris receives a nasty gash on the chin during an incident, and tweets a photo of the injury (which he later deletes), including the caption, "How u party wit rich n—s that hate? Lol... Throwing bottles like girls? #shameonya!"

Also among the injured are an Australian woman named Hollie, who says she had sixteen stitches and a tetanus shot after the incident, and basketball player Tony Parker, who says he suffered a scratched retina.

Rihanna and Drake: A Timeline of Their Maybe-Relationship (PHOTOS)
Credit: via Twitter    

Rapper Meek Mill, also present at the nightclub, tells XXL a few days afterwards that neither Chris nor Drake were to blame. “Things just happen in the club," he says. "I seen girls in there throwing bottles ... All types of people. I never seen Chris Brown or Drake throw a bottle and I was there.”

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A lawsuit filed by Breezy's bodyguard would later allege that the fight started over "a heated, acrimonious, and ongoing rivalry for the affections of Rihanna," and that things came to blows that night when “Drake requested that a person employed by [the bar] as a server, who was providing… excessive amounts of intoxicating beverages, deliver a note to Chris Brown. The note stated, 'I am f—king the love of your life.'”

February 10, 2013: Having reconciled in September 2012, Chris and Rihanna have just broken up — again — and a source tells The Sun it's because of Drake.

"Chris and Rihanna had a big bust-up at the Grammys over Drake. She was messaging him and Chris saw and it didn't go down well," dishes the source. "Since that night they have barely spoken and have been doing their own things."

March 9, 2013: Chris celebrates International Women's Day by addressing all the men in a club full of people: "You gotta say one thing to her… 'Don't make me have to tell you again that that's my p—y, baby." After his rant, Chris flips a double-bird at a DJ who is spinning his rival’s music and says, "The DJ can play this s—, but I want you all to know, f—k Drake!"

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April 12, 2013: In an interview with Elliott Wilson on the Keep It Thoro radio show, Drake lets loose on his feud with Chris… and how it relates to their mutual ladyfriend Rihanna.

"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," Drake says. "I did what a real n—a would do and treated her with respect."

June 2013: Drake, while discussing his feud with the rapper in GQ, says, "I get a feeling it could end really badly." It's unclear whether he's talking about his and Chris's feud, or Rihanna's safety.

2013: Are They or Aren't They?

July 3, 2013: Rihanna's buddy Melissa Ford posts a video to Instagram of RiRi dancing to Drake's verse in A$AP Rocky's "F—in' Problems." It may or may not have been a dig at Chris, with whom Rihanna had called it quits again that May, but obviously she's diggin' what he's doing.

July 10, 2013: Rumors once again resurface of another try for Rihanna and Drake. “When she was dating Chris, he [asked her not to talk] to Drake," a source tells Hollywood Life. “She really missed him in that time — yes, they went out years before but he was also a good friend to her — so calling him was one of the first things she did when she realized she was over Chris.”

“[Drake's been] waiting patiently on the sidelines," the source adds. "Just over a month ago, Drake gave Rihanna an ultimatum. He told her he needed to move on if she wasn’t going to commit. His love life was paused when Chris and Rihanna reunited, and Drake claims it caused him stress headaches, writer’s block and anxiety. He was obviously sick of it, but Rihanna wasn’t ready for him."

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August 23, 2013: RiRi and Drake are spotted together at the Sons of Essex restaurant in New York City, according to the chef, as well as a fellow diner, on Twitter. An eyewitness told Life & Style the pai "even shared a kiss."

September 20, 2013: Drake crushes shippers' dreams on Ellen, when asked by host Ellen DeGeneres about him and RiRi.

"Yeah, great girl…” Drake starts, uncomfortably. “We had our moment. Always support and have love for her and yeah …"

Drake cuts himself off. "I heard myself saying something else and I know I'm going to watch it back and be like, 'That wasn't what I thought I said...'"

When offered a do-over, he comes out with, "I'm not into do-overs. In any way." Yikes. Ouch. Sad faces.

October 25, 2013: Rihanna makes a Drake reference when posting her Medusa-inspired British GQ cover to Instagram. "Medusa head on me like I'm 'luminati," she says, which is from Drake's verse in the Migos song, "Versace."

November 19, 2013: The rumor mill places the two at dinner and a hotel together, after they coincidentally both have tour dates in Dallas the same weekend.

Early 2014: European Whirlwind Romance, Do-Over

February 2014: Amid renewed romance rumors, Drake denies dating Rihanna in an interview with Rolling Stone, which is published online February 13. "She's the ultimate fantasy. I mean, I think about it. Like, 'Man, that would be good.' We have fun together, she's cool and s—. But we're just friends. That's my dog for life."

"Ultimate fantasy," huh, dude?

February 13, 2014: Drake reportedly sends champagne and white roses to Rihanna's mom for Valentine's Day, who we all know RiRi is totally besties with. Awwww!

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February 24-25, 2014: Drake and Rihanna are spotted canoodling in Paris, where Drake is performing. Not just once, either — reports of RiRi and Drake last all weekend long! The pair are spotted at a restaurant one night, then the next evening at a nightclub… and the Hyatt Hotel. Oooooh! Maybe she's charmed by that "ultimate fantasy" comment?

February 26, 2014: This time, Drake and RiRi's public appearance is on purpose! Right after the pair are spotted galavanting about the City of Light, video footage surfaces of Rihanna grinding on Drake at his concert the night before. It's really, really hot.

March 7, 2014: Next stop: Amsterdam! Drake and RiRi throw on their warmest coats and grab sushi together in the Netherlands capitol.

March 8, 2014: No word from Drake or RiRi's reps on the rumored rekindling of their romance yet, but Rihanna's ex Chris Brown's rep says, "[Chris] is focused about his recovery. He only wants the best for her and is happy that she found someone."

March 9-10, 2014: Drake and Rihanna continue their European rumored-romance tour with a stop in London! The singers are spotted getting dinner in the UK on Sunday, March 9, and once again, the pair leave the restaurant separately sneaky, but not sneaky enough! The next night, the duo hit the Cirque le Soir nightclub in Soho together.

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March 11, 2014: The pair appear to be traveling together! After being seen canoodling in Paris, Amsterdam, and London, Rihanna and Drake are spotted leaving a club in Manchester in the wee hours of the morning — holding hands.

March 16, 2014: Aww! In one of the more concrete relationship rumors in this ever-expanding saga, multiple sources claiming to be "extremely close to the couple" tell TMZ they're totally boyfriend-girlfriend. One source even adds Drake is "in the best mood he's been in a long time."

March 25, 2014: Despite rumors that going steady hadn't exactly worked for them, the pair are photographed hitting the clubs in London together. Breakup, schmeakup!

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April 3, 2014: Our hearts, they're breaking! After seeing RiRi and Drake out together less and less frequently, Drake releases a track full of all his trademark super-feels with some apparent references to Rihanna built in.

"Waking up in Amsterdam with the boy / Long flight home, another xan for your boy," he sings on "Days In the East." "You would probably fly out to Japan for the boy / You would probably kill another man for the boy."

That does sound a whole lot like that globetrotting the pair did in this phase of their relationship epic. But this: "Why you keep askin' me about her? She's not here right now." What does it mean?

April 9, 2014: Well, this one's hard to ignore: Finally, after a couple of months of shying away from cameras and leaving clubs tens of minutes apart, Drake and Rihanna let all their PDA out in front of photographers at a Los Angeles Clippers game. Finally.

April 15, 2014: Rihanna flies with Drake to Palm Springs, California, and waits in the wings while her reported man kills it at the Coachella music festival.

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April 18, 2014: Rumors start flying about things getting a little extra serious between Drake and RiRi, with some semi-questionable sources telling The Daily Star that Drake bought her a serious rock with a reported estimated worth of $42k.

Rihanna is delighted with the gift, the source says of her bright-shining new diamond. She has accepted it as a token of Drake's love.

May 11, 2014: No, no, no, no. Hollywood Life sources lend some really distressing gossip to the mix: Drake and Rihanna's romance has cooled off after Drake called her "needy." Um, who was the one that bought a $42,000 ring just for funsies?

While we don't want to believe it, just a few days after the "needy" rumors hit the scene, sources tell Us Weekly the pair has broken things off. Reports keep rolling in after that this is the time they really broke up, or that RiRi is avoiding her beau's calls to avoid the real breakup, but nothing positive, but the vague consensus among all these reports is that things are basically over.

Meanwhile, the pair's reps have not commented on the relationship or its reported end at all.

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But the show goes on. RiRi keeps shining bright like a diamond, although sources tell Hollywood Life that she'll be "more guarded and reserved" in the future. Drake keeps holdin' on and, if some sketchy reports hold any veracity, gets kinda freaky with groupies (NSFW text!).

​​​​​Summer 2014: Wait, Another Do-Over?

August 5, 2014: As Summer 2014 drags on, things appear to have totally fizzled between Drake and RiRi. While they hit some of the same parties, sources say they do not interact at all. Drake even kind of becomes friends with Breezy, because we're living in bizarro-world.

However, their relationship is about to once again get a moment in the spotlight, all thanks to some creative fan interpretations of Drake's visuals at his August 3 show in Toronto which appears to show a devilish RiRi along with the most sinister numerical sequence, "666," during "Days of the East."

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So, did Drake let out some baggage in a very, very public place? Not so fast.

"My album title is VIEWS FROM THE 6. The 6 is Toronto," Drake clarified in an August 6 tweet. "Rih is a great girl who I know is about to kill this tour with Eminem. Its all love!!"

While some might think that would be the end of it, the incident appears to have given the two a chance to get talkin' again and if sources are to be believed, Drake did it on purpose to get his on-and-off flame's attention. And so begins Drake and RiRi, Phase Three! (Or is it four? Who knows.)

August 18, 2014: Drake and RiRi once again start hitting up some clubs together and are caught on camera at Griffin in NYC on August 18. Sources tell Hollywood Life this isn't just a chance meeting, but a chance for Drake to apologize about that whole 666 mix-up.

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Right off the bat, he apologizes to her, says the source, for being a dick and for disrespecting her in front of the whole world with that devil reference.

August 19, 2014: RiRi continues to not leave Drake's side, popping up at his concert in Queens the next night and hitting up some parties with him afterwards.

What's going on here? We're waiting with bated breath!

PS: Want more celebrity relationships? Check out Nina Dobrev and Ian Somerhalder's relationship timeline right HERE!