Rihanna And A$AP Rocky: An In-Depth Timeline Of Their Relationship And Dating History

Singer, actress, and business mogul Rihanna and her lover New York rapper A$AP Rocky are expecting their first child together! The couple—both 33 years old—were spotted together in New York City over the weekend as paparazzi snapped away at the hot pair while they took a stroll in Harlem!

View this post on Instagram

A post shared by The Hip Hop Agenda® (@thehiphopagenda)

So how did Rihanna and A$AP Rocky become one of the flyest couples in the game? Here’s what you need to know:

Early years…

Chris Brown and Rihanna met when they were two young, up-and-coming entertainers in the music industry in 2005. 

However, they did not start dating until 2007. In Feb. 2009, the couple had a scandalous split when it was revealed that Brown had physically assaulted Rihanna on their way home from a pre-Grammys party. But we don’t have to relive those moments.


In May 2009, Rihanna and Drake were rumored to be secretly dating. The two were seen together at Lucky Strike Lanes & Lounge in New York City. There were no photos, but this was the first time Rihanna and Drake have been linked together romantically.

“She was drinking whiskey and apple juice and making out with him all night,” a source told Page Six. The two would later be spotted here and there on the scene together, but nothing ever became official.  


After her first split from Chris Brown, Rihanna began dating professional baseball player Matt Kemp. The pair sparked dating rumors after being snapped together on New Year’s Eve in 2009 and then on a trip to Mexico in early 2010.

On Jan. 4, 2010, Rick Ross previewed Drake’s verse from “Made Men.” Drake dropped a bomb on the rumor mill with this line from the song.

“One of my baddest women ever, I call her Rihanna… / But that’s ’cause her name is Rihanna…”

On April 23, 2010, during a concert, Heartbreak Drake previewed verse 2 from “Fireworks,” where he raps about Rihanna. And telling The New York Times that she treated him like a pawn after he wrote a song for her and it never got released.

“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.'”

In May 2010, the former LA Dodgers outfielder raved to Us Weekly, “Yeah! That’s my girl! She’s just a fun person. I love to be around her.”

On Oct. 15, 2010, “What’s My Name” was leaked, just weeks after Drake told MTV about his new song with Riri. The pair released “What’s My Name?” and made a steamy video together.— Riri and Matt Kempt reportedly broke up by Dec. 2010 due to the “Bitch Better Have My Money” singer’s busy schedule.


The first big star that Rocky was ever romantically linked to was fellow rapper Iggy Azalea. The duo first started dating back in 2011 after being introduced via a mutual friend, and things went well between the couple for a while. At one point, Iggy even got Rocky’s album title Live.Love.A$AP tattooed on her finger. Nonetheless, they split about a year after that, and Iggy went on to get the “A$AP” part of the tattoo removed from her finger.


Rihanna and A$AP Rocky linked up to work together for the first time. The Bajan singer put out her “Cockiness” remix, which featured a hot verse from the Harlem rapper.

In September, the duo performed their rhythm thumping song at the 2012 MTV Video Music Awards. During the performance, Rocky grabbed a handful of Rihanna’s booty and planted a kiss on her cheek. This moment was so iconic in pop culture history because it initially sparked the idea of them being an item and quickly went viral across the internet.

When Rocky’s father died in late 2012, Riri sent him her “most sincere condolences” on Twitter, even throwing up the hashtag #BajanBlood.


The collaboration proved to be a great success as that led to Rocky becoming the opening act for Rihanna’s Diamond World Tour. 

A few months later, on Sept. 26, 2013, coming off the success of their tour, the New York native paid tribute to his friend with a shoutout in his song “Fashion Killa,” from his Jan. 2013 album, Long. Live. A$ AP. — It was clear the two had chemistry together as they both looked the part of a fashionably obsessed couple.

Still, by Feb., Rocky was linked to model Chanel Iman. Chris Brown and Rihanna briefly reunited in early 2013, with the “Love the Way You Lie” singer telling Rolling Stone at the time, “I decided it was more important for me to be happy… Even if it’s a mistake, it’s my mistake.” By that April, however, they had broken up for good.


Rocky and Chanel Iman got engaged in April 2014 but split for good in Oct. of that year.

Rihanna’s life changed in 2014 when she signed a six-album record deal with Def Jam Records. 


When she first released her album in 2015, it did not take long for Rihanna’s talent to be recognized. On May 27, 2015—after years of ongoing and continuous speculation—A$AP Rocky cleared up all the rumors in an interview with Hot 97.

“It never happened,” he said. “If it happened, then it would have happened! We didn’t do that!”

Rihanna was caught getting close to another famous face: Travis Scott. TMZ obtained footage of the “Work” singer and the “Sicko Mode” rapper making out at a New York Fashion Week party in September 2015.

They kept their fling under wraps, but when Scott was asked about the “Umbrella” singer for his Complex cover story later that year, he told the interviewer to not “do [me] like that, man.” 

Then, when asked to describe her in three words, he said “creative,” “inspiring,” and “muse.”


Well, remember those Drake rumors? In 2016 the pair collaborated twice with the sultry hit single “Work” and “Too Good,” which appeared on Drake’s album Views.

The two confirmed their connection when they subliminally got matching camouflage shark tattoos to symbolize their romance! The camo-shark body art represented a significant milestone for Rihanna and Drake—who dated on and off—from 2009 to 2016. 

The tattoo appeared to be inspired by the stuffed animal the rapper held in a photo he posted, congratulating his then-sweetheart on the night of the MTV Video Music Awards. 

View this post on Instagram

A post shared by champagnepapi (@champagnepapi)

While presenting Rihanna with MTV’s Video Vanguard Award in August 2016, Drake said of the pop star:

“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. She’s a living breathing legend in our industry.”

Just days after Rihanna first debuted her shark ink. In September of that year, the Canadian rapper appeared to have the same tattoo on his right forearm during the New Orleans show of his Summer Sixteen tour. 

View this post on Instagram

A post shared by Bang Bang Tattoo (@bangbangnyc)

After her split with rapper Drake, Rihanna shocked the social media world as she was photographed with a mystery man holding her hand! The mystery man turned out to be Hassan Jameel, a Saudi Arabian business mogul! 

Rumors of Rocky and Kendall Jenner being romantically linked to one another began in 2016. Although the two were friends for quite a while before the rumors, that year marked a significant number of public outings for the duo in various international settings. 


The pair were reportedly all over each other at Coachella 2017 as well as that year’s Met Gala. Despite these steamy moments, neither Kendall nor Rocky ever confirmed that they were an item.

In June 2017, Rihanna was spotted making out with Saudi businessman Hassan Jameel while on vacation in Spain.

Things appeared to be taking a serious turn when Jameel was seen out to dinner with Rihanna and her mom. Their relationship was kept primarily out of the spotlight.


On May 3, 2018, Rihanna revealed to Vogue that she and Drake no longer “have a friendship,” adding that they are not “enemies either.” Speaking on the situation, she said: “It is what it is.”

On Jun. 21, 2018, A$AP Rocky and Rihanna were spotted at Virgil Abloh’s 1st show as Louis Vuitton’s Artistic Director. Smiling sitting next to each other front-row speculation started to percolate again about what could be a possible romance. 


On Dec. 2, 2019, after attending Rihanna’s Diamond Ball for the 2nd consecutive year in NYC, A$AP Rocky walked the red carpet with RiRi for the British Fashion Awards! Dressed in an elegant mint dress, Rocky wore an all-black tux that Rihanna designed. 


In January 2020, Rihanna and her lover called it quits after nearly three years together. A source told People, “Their lives were too different, and it was hard to maintain a relationship.”

Rumors began to surface again after the breakup that Rihanna had gained more interest in longtime friend A$AP Rocky! The two had shared a hotel in New York City but still weren’t trying to put a label on it. 

In August 2020, Rihanna’s Fenty line expanded making her one of the wealthiest superstars ever. Her advertising campaign for Fenty Skin featured the pretty boy himself, A$AP Rocky, as a model.

After reports that their relationship was official, TMZ spotted the couple masked and bundled up out in New York City on Dec. 9, 2020— Which seems to be their favorite place to be! 

On Dec. 24, 2020, the couple was spotted together in Barbados. Spending time with friends and family as both have ties to the land. They seemed to be in great spirits as they were seen sharing each other company on a yacht. 


On Apr. 12, 2021, Rihanna and Rocky seemingly were no longer hiding their relationship as paparazzi spotted the pair in Los Angeles unmasked together.

On May 19, 2021, Rocky expressed himself to the world in an interview with GQ about how much he’s in love with Riri. Calling her the “love of his life” and addressing her as “my lady.” Revealing their romance had hit off the summer prior when they rented a tour bus and went on what he called “The Great American Road Trip.” Also stating, “She amounts to probably, like, a million of the other ones. I think when you know, you know! She’s the one!”

Bad Gal Riri and Pretty Flacko were photographed at Barricade in NYC. It was a definite rare PDA moment as the couple could be seen sharing a kiss. Paparazzi spotted them leaving the venue as Riri wore Rocky’s coat, and he held his arm around her as they made their exit on Jun. 23, 2021. 


Eagle-eyed fans noticed something missing when Ri hit the town with A$AP — her shark tattoo. The singer had gotten the ink on her ankle to the match former flame Drake’s in 2016. Instead of the aquatic predator, fans noticed that a crown appeared to have been inked in its place.

On Jul. 10, 2021, after being seen in the studio together, the couple was spotted in New York shooting a music video. People in the area snapped pictures of the two holding hands and looking as stylish as they always do. Of course, this is just one of several NYC-based dates the two were spotted on.

On Jul. 22, 2021, Rihanna and Rocky went out on a date in Miami spotted at the World Famous House of Mac. The two shared a moment and took photos with the restaurant owner Derrick Turton, the former manager of star Pitbull.

View this post on Instagram

A post shared by World Famous House Of Mac ™ (@worldfamoushouseofmac)

August 2021 Rihanna officially became a billionaire from her numerous endeavors like Fenty Beauty and Savage x Fenty. It seems that, perhaps as a way to celebrate, she and her boo, Rocky, went on a shopping spree around New York City.

September 2021, the two stars arrived at the infamous Met Gala as a couple– making this their first public outing and confirming their relationship wholly for the media. They coordinated with chic, baggy outfits and quickly stole the show.

November 2021, A$AP Rocky performed at ComplexCon in Long Beach, California. While he was on stage rapping and engaging with the crowd, Rihanna was in the audience hyping him up and being his biggest fan.


On Jan. 31, 2022, Rihanna and A$AP Rocky revealed that they were expecting their first child. The couple was seen making their way thru New York City. Riri looked happy as ever, showing off her belly to the paparazzi as they snapped away. 

View this post on Instagram

A post shared by badgalriri (@badgalriri)

A decade worth of friendship turns into love and a new life!