Traveling all the way back in time to the year 2005, Rihanna was just a teenager, and her debut song “Pon De Replay” (meaning “play it again” in Bajan Creole) was topping the charts. According to Drake, this was also the year that the stars aligned and the two soon-to-be megastars met for the first time.

In 2016, Drake gave a speech about the “Umbrella” singer at the MTV Video Music Awards (via YouTube). He said, “The first time I met Robyn Fenty was 2005. 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.” Little did they know that this brief encounter at a restaurant, shooting a music video, would lead to a romantic relationship just a few years later.

Rihanna dated “With You” singer Chris Brown for a couple of years beginning in 2007, but the relationship infamously took a dark turn after Brown assaulted her in February 2009. The images of Rihanna’s swollen and bruised face went viral, and the pop star couple was no more. Just three months later, in May of 2009, it was reported that Rihanna and Drake had officially gone on their first date.

The pair were spotted with some friends at a bowling alley called Lucky Strike Lanes & Lounge in New York City, and according to a source for Page Six, they were locking lips the whole time. “She was drinking whiskey and apple juice and making out with him all night. They were really cute together,” said the source. The outlet reported that Rihanna and Drake left at around midnight and what went on afterwards was a total mystery to the public. That is, until Drake released his 2010 song “Fireworks,” in which he referenced that night. Although the lyrics remain vague, they allude to a potential hookup as he rapped, “Who coulda predicted Lucky Strike would have you stuck with me? / What happened between us that night, it always seems to trouble me.”

Even after being caught making out with the “One Dance” rapper, Rihanna maintained that they were just friends for years. In November 2009, she spoke about her relationship with Drake in an interview with Angie Martinez on Hot 97 (via YouTube). When asked if there was any truth to the rumors that she and Drake were together, the “S&M” singer responded, “No, me and Drake, we’re friends, we’re still friends actually.”

Martinez continued to press, asking whether the singer had been checking Drake out, but Rihanna replied that she prefers “hot, older men.” She did, however, admit to hanging out with the rapper a few times, but insisted that nothing more was going on. “I’m actually not dating,” she said. “I just flirt.”

If you didn’t take Rihanna’s word for it in 2009, Drake’s dad Dennis Graham told TMZ a similar story in 2016, echoing that the relationship between the duo is nothing but platonic. “They’re just friends,” the rapper’s dad insisted.

In June 2010, after his brief rendezvous with Rihanna, Drake sat down with the New York Times a few days before his debut album “Thank Me Later” was due to drop. He was asked about a number of the songs on his album, including “Fireworks,” which was already widely known to be about the Bajan songstress. “I 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 said.

Less than a week later, Drake spoke to MTV to clarify the comments he made about Rihanna, saying, “I feel like when people write about it or try to take an excerpt from me describing it, it’s gonna sound negative. And in no way was it negative.” He went on to describe himself as extremely confident and that he was caught off guard because Rihanna is an “overwhelming and incredible person,” and she made him feel “small” and “nervous.” Drake spoke highly of her until the point he was asked about their kiss at the bowling alley. He remained tight-lipped, and through a smile said, “I don’t know what you’re talking about.”

Drake and Rihanna have been jointly working on hit songs since 2010, with their first collaboration released during Rihanna’s red hair period. “What’s My Name?” was a fun and suggestive pop tune that landed itself at the top of the charts, giving Rihanna her third number one hit that year. The music video was the first glimpse fans had at the pair’s undeniable chemistry, as they got steamy in a convenience store of all places.

A year later, Drake released “Take Care” featuring Rihanna, which became another fan favorite. Then came 2016, which saw what are arguably Drake and Rihanna’s best projects together, “Too Good” and “Work.” All of the music videos the duo have shot together have depicted Drake and Rihanna embracing, getting close, and in “Work,” grinding up on each other.

You could argue that this is all Hollywood-centric direction to hike sales, but their onstage presence together tells another story. Many of their live duets have been hot and heavy, and Rihanna and Drake’s 2011 Grammy performance was even dubbed “sexually charged” by PopCrush, as they danced together suggestively. During a 2016 Manchester concert (via YouTube), Rihanna and Drake broke down into laughter and embraced shortly before Rihanna danced up on the rapper. There’s acting, and then there’s authentic connection; Rihanna and Drake fans have often contended that the two singers broadcast their genuine attraction for one another, both on stage and in their music.

We all know how things went down between Chris Brown and Rihanna in 2009, and the “Forever” singer got a lot of heat for the way he treated her. Years later, in April of 2013, Drake took shots at Brown that fueled even more rumors around the supposed romance between him and Rihanna. On the “Keep It Thoro” radio show, Drake referred to Brown saying, “Don’t ask me s*** about that man when I come up here … 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.”

After the harsh criticism, it’s no wonder that in June of the same year, Drake and Brown were involved in a fight at a nightclub in New York City. Speaking with GQ, Drake addressed the brawl, saying, “It’s embarrassing, the amount of media coverage. Two rappers fighting over the woman. He’s not even a rapper, but still, it’s the last way you want your name out there.” He refused to address Rihanna by name, but everyone knew who he was referring to and fans knew that the beef indeed was over the “Rude Boy” singer. Drake and Brown have since squashed their beef, but it took them a long time to get there.

Nearly every time Drake has been asked about Rihanna or been in the presence of her, he can’t seem to hold back his praise. Some might argue that his outspoken admiration for the “Disturbia” songstress sometimes takes on a note of being hopelessly romantic. Drake has also hinted many times at their past relationship without making clear what happened and when. In a 2014 interview with Rolling Stone, he said, “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.”

While on “The Ellen Degeneres Show” in 2013, Drake was asked to confirm whether or not he’d dated Rihanna. “We had our moment,” he replied. He added that he will “always support and have love for her,” but left it at that. Degeneres remarked that he seemed “a little nervous,” which Drake played off with a laugh. Whatever did transpire between Drake and Rihanna, it’s clear that it didn’t impact the respect and appreciation Drake felt for her after the fact.

Drake, Rihanna, and even Drake’s dad can deny the apparent relationship as much as they want, but the photographic evidence has been pretty damning. In 2014, the twosome were spotted in London enjoying a day of shopping, followed by a fancy dinner in Mayfair and an all-nighter at the nightclub. As they were leaving the club at 4:30 am, Drake and Rihanna were seen holding hands in the back of the van they were leaving in. A source told Mirror, “[Drake]’s in the best mood he’s been in a long time.”

Some years passed before Drake and Rihanna were again spotted showing PDA, this time in Miami. The two were seen at a nightclub and a source told E! News, “Rihanna and Drake were happy, not hiding and totally affectionate in front of everyone. At one point they were kissing and holding each other.” A couple of days later at Drake’s concert in Miami, fans went wild when he invited Rihanna on stage. The two shared a kiss and then embraced as concertgoers screamed their approval.

Their on-again-off-again relationship seemed to take a toll, and Drake seemed to keep his distance from Rihanna for a little while in 2016. He was at one point spotted “getting cozy” with Hailey Bieber (back when she was Hailey Baldwin) on Memorial Day 2016, according to a source for People. This unlikely pairing didn’t last, of course, as she went on to marry Justin Bieber in 2018.

Later in the year, Drake made an appearance at Rihanna’s Manchester concert and they continued their, as Vogue hilariously put it, “long history grinding on stage together.” They danced together on stage in their classic fashion to their hit “Work,” and again sent the AubRih rumor mill into overdrive. A source told People, “Hailey [Bieber] was a fling, but Drake has always wanted to make things work with Rihanna.” The insider added, referring to the singer and rapper, that, “They are still dating. Things get more serious when they’re in the same place.”

Sometimes, Rihanna and Drake’s PDA was adorable, and fans were filled with hope that they were together at long last. However, there was one incident in particular that went viral and left many cringing. In 2016, when Drake presented Rihanna with the MTV Vanguard Award, his speech (via YouTube) was honest and heartfelt as he commended the “We Found Love” singer for the success she’s achieved in her career thus far. He then said, “She’s someone I’ve been in love with since I was 22 years old. 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.”

As Drake handed the award to Rihanna, he leaned in for a smooch and she maneuvered so his peck landed on her cheek, and he could be seen mouthing the words, “That wasn’t funny,” afterwards. The “Wait For U” rapper caught a bit of heat from onlookers, as Grazia Daily reported that his romantic gesture was unfair on Rihanna and overshadowed her big moment. This made for what might have been the most awkward celebrity PDA moment of the year.

After years of rumors, Drake and Rihanna gave their fans another reason to ship them together in 2016: matching tattoos. In August 2016, just a couple of days after the MTV Video Music Awards, a stuffed camouflage-printed shark made a few appearances in photos with Drake and Rihanna. Fans announced that Drake had bought the stuffed toy as a gift for the singer at a museum and, not even a couple of days later, Rihanna was sporting some new ink on her left ankle.

The tattoo of a camouflage shark was shared by Bang Bang Tattoo on Instagram, with Rihanna tagged on the post. Fans were quick to spot Drake’s tattoo of a familiar camouflage-print shark on his arm at his New Orleans show in September 2016, a few days after Rihanna’s ink was shared.

Jump ahead to June of 2021, and Rihanna’s shark is no more. AubRih shippers were devastated to learn that the “Love the Way You Lie” songstress had her ankle tattoo covered, opting for a crown instead. This was one of the many signs there was a rift in Rihanna and Drake’s relationship.

Those who were dying for Drake and Rihanna to finally fess up and announce that they were an item heard some unfortunate news in 2018. In an interview with Vogue, Rihanna reportedly winced when Drake’s name was brought up. She first addressed the MTV Music Video fiasco, saying, “Waiting through that speech was probably the most uncomfortable part. I don’t like too many compliments; I don’t like to be put on blast.”

Rihanna then uttered the words that would devastate countless fans. In reference to Drake, she remarked, “We don’t have a friendship now, but we’re not enemies either. It is what it is.” While this could very well have been yet another time she downplayed her relationship with the rapper, her 2021 tattoo coverup seemed to seal the deal. And just like that, Rihanna and Drake were no more.

By the time Rihanna announced that she and Drake didn’t have a relationship anymore, Drake had already become a father. His son, Adonis Graham, was born to the rapper and French artist Sophie Brussaux on October 11th, 2017. Drake and Brussaux reportedly had only a brief fling, but the pregnancy could have been one of the reasons he and Rihanna ended their years-long relationship.

Rihanna and A$AP Rocky were spotted together for the first time in January of 2020 and became an official item by December. After about two years of dating, it was announced that Rihanna and her beau were expecting — and according to a source for Hollywood Life, Drake might have taken the news a little hard. “He had mixed emotions. Of course, he was ecstatic for her because he knew she had always wanted children. But at one point in time, Drake saw himself having a future with Rihanna so it was just further confirmation that there was no future for them,” they said. The source added that he did text to congratulate Rihanna and A$AP Rocky, but it was also reported that the rapper unfollowed her on social media the same day.

During the 2023 Super Bowl halftime show, Rihanna revealed that she was pregnant with her second child with A$AP Rocky. It would seem that the “Umbrella” singer has finally found her match — and that AubRih is over for good.