Drake & Rihanna's Relationship Timeline Shows Just How Much They Keep Everyone Guessing

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When Rihanna released her new album ANTI, she included a track with Drake called "Work." Suddenly, it felt like pop culture jumped back a few years and it was 2010 all over again. After all, that was when Drake and RiRi first collaborated on "What's My Name?" In the music video, things got pretty heated in the milk aisle at the grocery store. Then, they made music again in 2012 and created another flirtatious video for Drizzy's song "Take Care." I'm sensing a pattern here: Record a song together, make a video, and restart the cycle of speculation about their love life.

For years, these singers have been the subject of on-again, off-again dating rumors. I can't be the only one wondering, did these two actually ever date? The answer is yes — well, kind of. (More on that later.) Plus, Chris Brown came back into the picture at one point, so things were bound to get messy. Their love triangle definitely reached its breaking point in 2012, but luckily, things are all good now.

To help you keep track of their history, here's an entire timeline of Drake and Rihanna's rumored relationship — including all of the ups and downs over the years.

May 2009

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The rumors began back in 2009 at Lucky Strikes Lanes & Lounge, a bowling alley in New York City. Page Six reported that Rihanna and Drake were spotted making out. There was whiskey and apple juice involved.

Despite this bowling date, a few months later she said in a radio interview they were just friends.

June 2010

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Apparently Drake was affected by their connection, writing a verse about RiRi on his song "Fireworks." In the track, he says,

He later told The New York Times that Rihanna treated him like a "pawn" — ouch! He elaborated, telling NYT,

October/November 2010

RihannaVEVO on YouTube

I suppose Drake didn't feel too "terrible," because later that year, the pair released "What's My Name?" together. In the song's video, the two cuddle up and get flirty at the grocery store. They're too distracted to cry over the spilled milk.

February 2011

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Despite a chemistry-filled performance of "What's My Name?" at the 2011 Grammys, these two still never made things official.

July 2011

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Then a few months later in July, TMZ reported that they showed some PDA at a Canadian night club — Drizzy's homeland.

February 2012

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Just when it seemed like things were finally going Drake's way, Rihanna's ex Chris Brown came back in the picture the following February. They collaborated on the Barbados native's track "Birthday Cake."

April 2012

DrakeVEVO on YouTube

Brown isn't the only one who made music with Rihanna. She collaborated with Drake again on "Take Care." The black-and-white video is rather intimate, don't you think?

At this point, things get complicated and confusing. It's almost like these two men were competing for Ri's attention. Actually, that's exactly what happened.

June 2012

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In June, a bar fight broke out between Brown and Drake's entourage. Brown even wound up with a gash on his chin, while Drake's rep claimed he was not involved at all. Still, rumors swirled that the alleged altercation could have been about Rihanna.

Law enforcement later told TMZ that neither Brown nor Drake would face criminal charges for alleged involvement in the incident. Phew!

September 2012

ROBYN BECK/AFP/Getty Images

Brown and Rihanna officially got back together and were spotted kissing at the MTV VMAs during a commercial break. Their reunion lasted from September 2012 through May 2013. Reportedly, Brown had to focus on himself instead.

In case you're starting to pity Drake, don't worry, he's not out of the picture just yet...

Fall 2013

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In August, Drake and Rihanna were spotted having dinner together in New York City. According to Vibe, they were both in town for the MTV VMAs at the Barclays Center.

Meanwhile in September, the Degrassi alum talked to Ellen DeGeneres about his romantic past. Speaking of RiRi, Drake said, "We had our moment." Keyword: "had." He definitely used the past tense there.

February 2014

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This is when things really get interesting. When talking to Rolling Stone in Feb. 2014, Drake said that Rihanna is his "ultimate fantasy." The two actually traveled to Europe together soon after and TMZ claimed they were officially a couple.

Meanwhile, Chris Brown's rep told  Page Six that Brown was "happy [Rihanna] found someone." This totally implies that the "Take Care" singers were indeed together. Unfortunately, their short-lived romance ended in May.

July 2014

HD Gyal on YouTube

Soon after, Brown and Drake buried their hatchet. They even performed in a skit together at the ESPYs.

Spring 2015

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In April, Drake and Rihanna hung out at Coachella for the second year in a row. Onlookers said they looked "couple-y."

Then in May, the pair was spotted in a recording studio together for three hours. Reports said that things got steamy in the studio, aka they allegedly spent most of the time making out — not making music.

November 2015

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Just when you thought the whole story makes sense and wraps up nicely, Rihanna told Vanity Fair in November 2015 that her last "real, official boyfriend" was Brown. In other words, the fling with Drake didn't even count as something substantial in her mind. Poor, Drizzy!

January 2016

RihannaVEVO on YouTube

Despite Ri's comments in Vanity Fair, it wasn't enough to deter the "Started From The Bottom" singer. The two collaborated on "Work" for Rihanna's latest album.

Fans will just have to wait and see what happens next. Maybe the timing will finally be right and Drake will get his "ultimate fantasy" once and for all.