Drake and Rihanna's Relationship: A Look Back

Photo: Kevin Mazur/WireImage

For nearly a decade,RihannaandDraketried to make it “work, work, work, work, work.”

After years of being in an on-and-off relationship, Rihanna revealed in 2018 that she and Drake were no longer close. Minus a few interactions since their breakup, both moved on, with Rihanna welcoming her first child with longtime boyfriendA$AP Rockyin 2022.

2005: Drake and Rihanna meet on the set of Rihanna’s “Pon de Replay” music video

It all started in 2005 at a diner in Drake’s native Toronto, where Rihanna shot the music video for her debut single “Pon de Replay.” Drake appears in the video as an extra.

May 18, 2009: Drake and Rihanna go bowling in N.Y.C. and are spotted kissing

TheNew York Post’sPage Sixreported that Rihanna and Drake were spotted making out at an N.Y.C. bowling alley following the end of Rihanna’s relationship with Chris Brown.

Drake went so far as to mention the memorable night in his song “Fireworks.” The lyrics for the 2010 track read: “Who could’ve predicted Lucky Strikes would have you stuck with me/What happened between us that night it always seems to trouble me.”

Rihanna quickly squashed rumors of a relationship, telling radio personality Angie Martinez in an interview that she and the up-and-coming rapperwere just friends.

June 13, 2010: Drake says in an interview that Rihanna treated him like a “pawn”

In an interview with theNew York Times, Drake opened up about his brief encounter 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.”

February 13, 2011: Drake and Rihanna perform together at the Grammys

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June 12, 2011: Drake and Rihanna are spotted cuddling in a Montreal nightclub

It seems as if the onstage chemistry between Rihanna and Drake carried into real life, as TMZ reported that they were spottedshowing PDA at a Canadian nightcluba few months later in June.

January 17, 2012: Drake releases “Take Care” featuring Rihanna

Rihanna collaborated with Drake on his 2012 single"Take Care."

The song’s lyrics are quite revealing: “Can’t deny that I want you, but I’ll lie if I have to / Cause you don’t say you love me to your friends when they ask you / Even though we both know that you do … you do.”

April 6, 2012: Rihanna is featured in Drake’s “Take Care” video

September 20, 2013: Drake calls Rihanna a “great girl” onEllen

February 13, 2014: Drake calls Rihanna his “ultimate fantasy”

Drake is not one to hold back, and a February interview withRolling Stoneproved no different. When speaking about Rihanna, the rapper described her as his"ultimate fantasy."

March 2014: Rihanna joins Drake on his European tour

While Drake toured Europe in March,Rihanna was spotted with him throughout the tour, fueling years-long relationship rumors.

November 2015: Rihanna tellsVanity Fairthat she is not dating anyone, including Drake

The “Kiss It Better” crooner toldVanity Fairin a cover story that her “last real, official boyfriend was Chris Brown,” despite months of rumors that she and Drake had been dating.

January 27, 2016: Rihanna releases “Work” featuring Drake

Rihanna released the duo’s latest collaboration, “Work,” in January 2016. The following month, Rihanna and Drake appeared in the song’ssexy music video.

May 4, 2016: Rihanna and Drake are “very affectionate” at her concert afterparty in L.A.

Drake appeared alongside Rihanna on her tour later in the year, recreating their sultry moves for concertgoers. Their chemistry became even more apparent at the afterparty following Rihanna’s concert in L.A. A source told PEOPLE that the two were “dancing all night together,” and Rihanna and Drake “were being very affectionate.”

Another source told PEOPLE the pair were purposely keeping their relationship secret. “They have been keeping it a secret because this time around, they want to do it right and keep their relationship private,” the source said.

June 2016: Rihanna gets in the studio with Drake on “Too Good”

Rihanna also appeared on Drake’s highly-anticipated albumViews, contributing vocals for"Too Good." The heart-wrenching single provided some insight into the pair’s complicated relationship.

The lyrics read: “And last night I think I lost my patience / Last night I got high as the expectations / Last night, I came to a realization / And I hope you can take it.” Rihanna seemingly insinuated that she placed the rapper in the friend zone.

July 2016: Drake and Rihanna are “back together”

After the rapper was seen briefly hanging out with budding model Hailey Baldwin,sources confirmed to PEOPLEthat Baldwin “was a fling.” The insider revealed, “Drake has always wanted to make things work with Rihanna.”

“They are still dating,” the source added, regarding Rihanna and Drake. “Things get more serious when they’re in the same place.”

Drake headlined his 2016 OVO Fest concert two nights in a row in his hometown of Toronto, and Rihanna appeared with him both nights.

August 2016: Drake surprises Rihanna with a billboard

Michael Loccisano/Getty

August 29, 2016: Drake congratulates Rihanna on Instagram

After honoring Rihanna at the VMAs, Drakecaptioned a photoof the pair looking cozy, “This is a night for us all to be thankful for what you have done for us!” He continued, “You have affected so many of our lives in the best way possible. Tonight we celebrate you!”

August 29, 2016: Drake and Rihanna share a kiss onstage in Miami

David M. Benett/Dave Benett/Getty

Later that night, Drake and Rihanna were spotted kissing at the Miami nightclub E11EVEN, which hosted the concert afterparty. Rihanna and Drake “danced, kissed, and acted really coupley,” a source said.

September 2, 2016: Rihanna thanks Drake on Instagram

In a lengthy Instagram post, the “Work” singer spoke about the night she received the Video Vanguard Award at the 2016 VMAs. “#VMA2016 night was one that I would never forget!! I have the most incredible people in my life!” she wrote, accompanying a clip of her acceptance speech. Rihanna also took a moment to mention the rapper: “[Drake] your speech was so touching and I love you for that!” she wrote.

September 2016: Drake and Rihanna get matching tattoos

Source: BangBangNYC/Instagram;Kevin Mazur/Getty

Just days after Rihanna showed off her fresh ink of a camouflage-print shark (reminiscent of a plush shark Drake once gifted her) on her ankle, the Canadian rapper appeared to have the same tattoo on his right forearm during the New Orleans stop on his Summer Sixteen tour.

October 2016: Drake and Rihanna reportedly have an “open” relationship

A few months after the couple became official, Drake and Rihanna were still going strong. The musical pair had not parted ways,a source close to the couple confirms to PEOPLE, with one source adding, “it’s an open thing.” However, the stars' reps had not yet commented.

February 20, 2017: Drake gives Rihanna a birthday shout-out during his concert in Dublin

The rapper gave a special shout-out to his former flame during his Dublin concert on Feb. 20, a.k.a. Rihanna’s 29th birthday.

“It’s somebody’s birthday today — somebody I have a lot of love for and a lot of respect for,” Drake said in fan-recorded videos.

“So, instead of singing ‘Happy Birthday,’ though, we just going to do this in Dublin. Instead of singing ‘Happy Birthday,’ we’re going to set it off just like this…” he said before shifting into a performance of “Work,” his collaboration with the singer.

May 3, 2018: Rihanna says she and Drake are no longer speaking

In an interview forVogue’s June issuepublished online on May 3, Rihanna admitted that she and the Canadian rapper are no longer close after more than a year since they were last seen together. “We don’t have a friendship now, but we’re not enemies either,” Rihanna said. “It is what it is.” The hitmaker also shared that she is happily taken, though she remained coy about her beau’s identity.

October 12, 2018: Drake says he wanted to start the “perfect” family with Rihanna

While appearing on the second episode ofLeBron James' talk showThe Shop,Drake confessed that he once thought his “perfect life"would be starting a family with Rihanna.

“As life takes shape and teaches you your own lessons, I end up in this situation where I don’t have the fairy tale, like, ‘Oh, Drake started a family with Rihanna and this is like so perfect,'” Drake said. “It looks so good on paper. By the way, I wanted that too at one time.”

May 20, 2019: Rihanna says she doesn’t plan on collaborating with Drake “anytime soon”

In an interview withThe New York Times’ T Stylemagazineabout her clothing brand and makeup line, Rihanna also discussed the music she was working on. When asked if her next album would include any collaborations with Drake,Rihanna responded, “Not on this album, that’s for sure.” She added, “Not anytime soon, I don’t see it happening.”

March 24, 2020: Drake encourages Rihanna to release new music on Instagram Live

June 23, 2021: Rihanna covers up her matching tattoo she got with Drake

Five years after Rihanna and Drake got matching shark tattoos, it appeared that Rihannachanged the ankle tattoo into a crownwhen a photographer captured a close-up photograph of her ankle while the beauty mogul was out in in N.Y.C. with current boyfriend A$AP Rocky.

source: people.com