All The Red Flags In ASAP Rocky & Rihanna's Relationship

Both fashion icons, both highly successful people, and both extremely good-looking, Rihanna and ASAP Rocky appear to be a match made in the stars. From their coordinated fashion moments to their undeniable chemistry, Rocky and Rihanna have built a partnership that many of their fans have come to adore. Unsurprisingly, the pair is never shy about showering praise on each other, with Rocky calling Rihanna his “perfect person” in an interview with Billboard. 

Similarly, the “Umbrella” hitmaker remains Rocky’s number one fan in life and art. “Being here tonight, it just feels great to see him achieve something that we always knew that he was a part of and influenced. I’m super proud,” the singer gushed to E! News at the 2024 Footwear News Achievement Awards where the “Fashion Killa” rapper was honored for his collaboration with Puma. But while these two might seem picture-perfect, several things about their relationship continue to raise eyebrows.

For instance, Rocky has not always been monogamous. In a 2015 interview with i-D, the rapper openly admitted he didn’t believe in the concept. “When the time comes to settle down, I might just have two girlfriends,” he said. He has however since walked back his statement, admitting to GQ in 2018 that monogamy is “so much better when you got the one.” But while Rocky and Rihanna’s love story seems to be going strong, some red flags in their relationship are too obvious to ignore.

Rihanna and ASAP Rocky first piqued the public’s attention in 2012 when they performed their song “Cockiness (Love It)” at the MTV Video Music Awards. The steamy performance, which saw Rocky grab Rihanna’s butt, foreshadowed the pair’s eventual romantic relationship. 

But while the performance remains a standout performance in the couple’s history, Rihanna later revealed that the unexpected butt grab was, in fact, not part of the plan.  “When he grabbed my a** that night, everybody thought I was about to … my team was worried that I wanted to have his head on a fuc**** mantle,” she explained in a cover feature for Interview. Instead of the expected reaction, Rihanna gave Rocky a pass, a move that hinted at her soft spot for the rapper. “I was like, ‘Ah, nah.’ “That’s why everybody was like, ‘Oh my god. She likes him,’ ” she added. 

But while the “Diamonds” singer had no problem brushing it off, there is no denying that Rocky grabbing Rihanna’s butt without her consent was a problematic move. Yet, a free pass was not all Rocky got as his connection with the singer only grew after the MTV VMA performance. In 2013, Rihanna invited Rocky to be the opening act on her Diamonds World Tour. Later that year, the singer also appeared in the music video for Rocky’s “Fashion Killa,” seemingly cementing their platonic bond.

Despite their long-standing history, Rihanna and ASAP Rocky approached their relationship cautiously. Speaking to Interview in April 2024, Rihanna reflected on the couple’s transition from friendship to a romantic relationship, revealing that there was a lot of hesitation in the beginning. “We knew what we were capable of, and the trouble that we could bring to each other’s lives. We could make or break each other’s hearts. And so, we started dating with a lot of caution,” she admitted.

Their years-long friendship however laid a strong foundation for their bond. The “Work” singer also spoke candidly about how her and Rocky’s shared interests and mutual support for each other’s work, brought them closer through the years. “We saw fashion the same. We saw creative the same. We ended up in the same circles a lot,” she explained. “And past that, when we grew up, we ended up supporting each other’s brands and products and creative all the time. I would wear his sh**, he would show up to my launches.” Still, when the time came for their friendship to evolve into something more, Rihanna let things unfold naturally, telling Interview that she “just let whatever was supposed to happen, happen.”

Evidently, their relationship has blossomed over the years, with the couple building their lives together, as they continue to expand their beautiful family.

In January 2022, Rihanna and ASAP Rocky revealed they were expecting their first child after debuting the singer’s baby bump in a street-style New York photoshoot. “Having a baby is something she was never focused on, but being with Rocky opened her up to the idea. She couldn’t be happier and is so excited to be a mom,” a source shared with People. Four months later, Rihanna and Rocky welcomed their first child, son RZA Athelston, with an insider confirming that the pair was “very excited to be parents.”

In a surprising twist, Rihanna debuted another baby bump during her iconic Superbowl halftime performance in February 2023, eight months after giving birth to RZA. A representative would later confirm to People that the singer was pregnant with her second child. By August 2023, the “Stay” singer became a mother of two with the arrival of her son, Riot Rose Mayer. “Rihanna feels her family is now complete. It’s something she’s always wanted,” an insider told People. 

But while Rihanna’s motherhood journey has sparked a lot of joy and excitement, it has also raised some concerns over the stress of raising two kids with such a close age gap. “Having two kids under 2 would be the most stressful sh** Rihanna would ever experience regardless of the maids she has,” one user wrote on X, formerly known as Twitter.

During a 2013 interview with Coveteur, ASAP Rocky shared his thoughts on beauty and makeup, noting his preference for “natural” women who don’t wear makeup in their daily lives. In the interview, the rapper suggested that makeup was harmful to the skin. “You girls don’t understand how much you mess up your skin. You can’t help it, but makeup is the worst thing you can do to your skin,” he explained. The “Am I Dreaming” rapper however noted that he would make an exception for special occasions or events where need to get “dazzled up.”

Rocky had more to say about red lipstick, which he labeled unsuitable for dark-skinned women. “You have to be fair-skinned to get away with that,” he added (via HuffPost). The famous rapper also criticized purple lipstick, noting that it “looks stupid on all girls.” Expectedly, Rocky’s comments were met with much scrutiny, with many finding them offensive and ignorant. In his response, the award-winning rapper described black women as sensitive and easily offended. “You can’t say nothing about they glasses, they nails, none of that because then you’re a womanizer or you’re a racist,” he said (via BET).

Today, however, Rocky’s comments come off as hypocritical. Not only Rihanna, his long-time partner, the founder of one of the world’s most popular makeup brands, but she has also been spotted wearing purple lipstick on countless occasions over the years. This contrast between Rocky’s opinions and Rihanna’s makeup choices suggests a double standard or perhaps even worse, a general lack of self-awareness.

In April 2022, ASAP Rocky was arrested during the investigation of the shooting and assault of his former friend, ASAP Relli. The Los Angeles Police Department confirmed the arrest in a statement, noting that the shooting had occurred in November 2021. “The suspect has been identified as 33-year-old Rakim Mayers, a Los Angeles resident, also known as music artist ASAP Rocky,” the department wrote in a statement shared via X. That same day, he was released on a $550,000 bail.

Four months later, the rapper was officially charged with two counts of assault with a semi-automatic firearm. George Gascón, the Los Angeles District Attorney at the time, released a public statement, condemning the discharge of a weapon in a public space and noting that it “could have ended with tragic consequences not only for the person targeted but also for innocent bystanders visiting Hollywood.”

In January 2025, the rapper’s 13-day-long trial case began, with Rihanna notably making regular appearances at the courthouse. While this appeared to be an act of loyalty, fans had mixed reactions, with some expressing frustration over the situation. “Being a black woman is something else. Even with a successful career and BILLIONAIRE STATUS, a man will still subject you to visiting courtrooms for his stupidity,” one person wrote on X. “This is proof that women will always make good decisions until they choose a man,” another person remarked. 

He is well known for his pretty face and signature braids now, but once upon a time, ASAP Rocky was popular for his controversial and misogynistic rhetoric. Back in 2015, Rocky stirred up drama after releasing “Better Things,” a track on which he made crude references to his fling with Rita Ora. “I swear that bit** Rita Ora got a big mouth/ Next time I see her might curse the bit** out/ Kicked the bit** out once cause she bit**** out/ Spit my kids out, jizzed up all in her mouth and made the bi*** bounce,” he rapped on the song. 

Unsurprisingly, the song was met with widespread backlash from social media users who accused him of degrading Ora. “Why do people think what A$AP Rocky said about Rita Ora was funny? It was plain misogyny. It’d be disrespectful to any woman,” one person wrote on X. “He already wasn’t likable. This is just disgusting,” another person commented. Though Ora was admittedly unbothered by the explicit lyrics, she had one major concern about Rocky and his song. “I think about it and I don’t want people to think it’s OK to speak about women like that. That’s it,” she explained during an interview with Hot 97.

But Rita Ora wasn’t the only woman Rocky has made questionable comments about. Over the years, the rapper has built a disturbing reputation for bragging about his sexual conquests in degrading ways. 

Speaking of conquests, ASAP Rocky has previously admitted to suffering from sex addiction dating back to his younger years. “I’ve been a sex addict for some time,” Rocky shared during a 2019 interview on Angie Martinez’ show (via TMZ). “These are things that people stay away from and they don’t like to admit.” The rapper explained that his addiction started in junior high school, leaving him unusually aroused long before hitting puberty. “Like, I was horny. I ain’t even have no sperm in my testicles yet, but literally just was horny,”  he explained. Rocky refuses to be embarrassed about it, instead accepting it as a part of who he was.

But not only was Rocky horny as a child, the rapper admittedly started having sex, and specifically, orgies as a teenager. “My first orgy was when I was in seventh grade. Thirteen years old. Yeah, I was at Booker T. Washington [Middle School] in New York City,” he shared in a 2018 interview with Esquire. To cater to his sexual needs, Rocky had his bed specially designed to accommodate the many orgies he had in his house. 

The “Peso” rapper also admitted to documenting his sexcapades, telling Esquire he usually caught it on camera. “The women that I’m around are into that free-spirited sh** like me,” he noted. Given his current relationship, one might wonder, has ASAP Rocky left all of this in his past, or is Rihanna in on all of these?