Drake and Rihanna's Relationship: A Look Back

For nearly a decade, Rihanna and Drake tried to make it "work, work, work, work, work."

The Fenty Beauty founder and "Falling Back" rapper first sparked romance rumors in 2009, their undeniable chemistry on full display in live performances and music videos. Drake even professed his love for the "Diamonds" singer at the 2016 MTV Video Music Awards.

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 boyfriend A$AP Rocky in 2022.

From their first-ever collaboration — "What's My Name?" — to keeping fans guessing about their relationship status, here's a complete timeline of Rihanna and Drake's connection over the years.

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.

While presenting Rihanna with the MTV Video Vanguard Award at the 2016 VMAs, Drake confirmed his cameo. "The first time I met Robyn Fenty was in 2005," he recalled. "I was introduced to her as the kid who played background music at the restaurant as people ate their dinner."

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

The New York Post's Page Six reported 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 rapper were just friends.

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

In an interview with the New 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."

October 26, 2010: Rihanna releases "What's My Name?" featuring Drake

The supposed bad blood between Rihanna and Drake quickly dissipated, and the pair eventually collaborated on Rihanna's song "What's My Name?" a few months later.

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

They may not have made things official, but Rihanna and Drake certainly sparked relationship rumors after their performance of "What's My Name?" at the 2011 Grammys.

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 spotted showing PDA at a Canadian nightclub a 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

After several delays, Drake premiered a music video for "Take Care" on April 6, 2012, on MTV. The video featured Drake and Rihanna embracing, including imagery reflecting the song's introspective lyrics.

September 20, 2013: Drake calls Rihanna a "great girl" on Ellen

Ellen DeGeneres surprised Drake by asking about his on-again, off-again relationship with Rihanna during an appearance on her talk show. Drake responded, "Yeah, great girl. We had our moment. Always support and have love for her and yeah …"

February 13, 2014: Drake calls Rihanna his "ultimate fantasy"

Drake is not one to hold back, and a February interview with Rolling Stone proved 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 tells Vanity Fair that she is not dating anyone, including Drake

The "Kiss It Better" crooner told Vanity Fair in 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's sexy 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 album Views, 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 PEOPLE that 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."

August 1, 2016: Drake says that Rihanna "might have to go half on a baby" with him

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

During the second night, Drake joked on stage, "You showed up two nights in a row for my city. You might have to go half on a baby." He then introduced Rihanna as "the greatest entertainer in the world, flying all the way in from God knows where … and looking good doing it too."

August 2016: Drake surprises Rihanna with a billboard

Days before the VMAs, Drake gifted the Barbadian beauty a larger-than-life sentiment in the form of a billboard, congratulating her on winning MTV's Michael Jackson Video Vanguard Award. RiRi posted a pic of the gesture on her Instagram with an emoji-filled caption.

August 28, 2016: Drake presents Rihanna with the MTV Video Vanguard Award

The pair's relationship had quite an impact on the "Hotline Bling" rapper, as he was quick to reveal when presenting Rihanna with the Video Vanguard Award at the MTV Music Video Awards. "She's someone I've been in love with since I was 22 years old," he said before embracing Rihanna and going in for a kiss. "She's one of my best friends in the world. She's a living breathing legend in our industry." After the show, the two grabbed dinner with friends and family, then headed to N.Y.C. hot spot Up & Down, where Drake "was literally shadowing her every movement and was just so affectionate and adoring the entire night," a source told PEOPLE.

August 29, 2016: Drake congratulates Rihanna on Instagram

After honoring Rihanna at the VMAs, Drake captioned a photo of 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

Things continued to heat up for the pair: A few days after the rapper professed his love for the singer at the MTV Video Music Awards, Rihanna made a surprise appearance at Drake's sold-out concert in Miami. And following a performance of her song "Bitch Better Have My Money," the pair came together and kissed before embracing.

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

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 for Vogue's June issue published 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 of LeBron James' talk show The 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 with The New York Times' T Style magazine about 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

On March 24, musician DJ Spade hosted a livestream on his Instagram, and both Rihanna and Drake joked with each other in the comments.

"Rihanna drop R12 right now," Drake wrote, according to screen grabs captured by the Pop Crave Twitter account. Rihanna, referring to Drake as "Champs," replied, "Give drake some water," to which he responded, "Hahahahhahahaha you have a bad attitude @badgalriri."

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 Rihanna changed the ankle tattoo into a crown when 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.