Rihanna & A$AP Rocky’s Complete Relationship Timeline: From Friends To Dating

Rihanna and A$AP Rocky. The pairing we’d quirked a brow at through the many years the influential artists have orbited each other. Their relationship has spanned decades and moved through the professional and personal, and now, come 2021, it seems that romance has well and truly blossomed.

From their earliest beginnings supporting each other in their respective music careers, to A$AP Rocky’s confession that Rihanna is the love of his life, here, their entire relationship history.

Settle in, this one spans friendship to ‘hanging out’ to casual dating to becoming one of the biggest celebrity couples on the planet.

The pair apparently spent the night partying into the early morning, with the video apparently taken around 6 am.

The couple also made headlines for this sweetly coordinating purple moment, once again from a date night in New York City.

Noting that he has quite a reputation as a ladies man, Rocky confirmed that he was enjoying the shift to a steady relationship. “So much better when you got the One. She amounts to probably, like, a million of the other ones. I think when you know, you know. She’s the One.”

Though they’ve thus far kept their relationship largely off social media, Rihanna and A$AP Rocky allowed a glimpse into their romance when the couple had a dinner date at Delilah in Los Angeles.

“New year’s resolution: apply the pressure,” was Rihanna’s caption for a low-fi Instagram showcasing her metallic ensemble.

A closer look at her shoes reveals that the strappy heels were ones actually designed by Rocky. The rapper collaborated with footwear designer Amina Muaddi on the Amina Muaddi x AWGE LSD Gladi Thigh Heel. You know, as worn by Rihanna.

A$AP Rocky spent Christmas of 2020 with Rihanna in Barbados, a moment he described as a “homecoming thing.” The couple were snapped multiple times throughout December riding jet skis, engaging in some PDA on a chartered catamaran ride and generally enjoying themselves in the water.

“Spending Christmas together was an obvious step for Rihanna and A$AP,” the source said. “They’ve known each other for so long as friends and in a work setting, which makes it so easy for them to get along, travel together and be involved in each other’s lives to the full extent. They always have such a good time together and definitely seem in love.”

Earlier in December, the outlet shared that one of the reasons for their connection was their shared heritage.

Rocky’s father is, like Rihanna, from Barbados, which he reflected on during his GQ interview. “It was crazy. I always imagined what it would be like for my dad, before he came to America. And I got to visit those places, and believe it or not, there was something nostalgic about it. It was foreign but familiar.”

Similarly, trust built through years of friendship also provided foundations for the relationship.

“A$AP has always had a crush on Rihanna and there’s a lot of love there on both sides,” added the source.

Earlier in the month—which yes, was heavy with reports from ‘sources’—it was reported to People that Rihanna is very happy with A$AP Rocky.

“They’ve been inseparable the past few weeks,” the source shared. “It’s a new relationship, but they both seem very into it.”

“They’ve always seemed to have a great time together,” said the source. “They have a lot in common. … They both are very much about helping out in the communities where they grew up.”

Some may recall that Rihanna’s relationship with the Saudi billionaire Hassan Jameel apparently ended due to lifestyle differences. It appears however, Rihanna and Rocky are better matched. “A$AP is generous, and so is Rihanna. A$AP is known for being a great guy.”

The beauty contained in the image of Rihanna and A$AP Rocky’s promotional photo for Rihanna’s Fenty Skin skincare line is rather breathtaking, but many also wondered if the pictures contained shades of romance too.

Now, in 2021, we know that the U.S. 2020 summer period was incredibly formative for Rihanna and Rocky’s relationship.

In his May 2021 GQ interview, Rocky revealed that the pair rented a tour bus over the summer and embarked on a “Great American Road Trip.”

Speaking about the summer Rocky explained, “I met myself.”

“Being able to drive and do a tour without feeling like it was an occupation or an obligated job agreement, I feel like that experience is like none other,” Rocky shared. “I never experienced nothing like it.”

Around the time that Rihanna split from her boyfriend Hassan Jameel, rumours began to circle that she and Rocky were romantically linked.

The source added, “It’s really casual between them and she’s not thinking about whether there’s a future with Rocky. She’s a newly single girl having fun.”

Is this an excuse to once again marvel at Rihanna’s look from the British Fashion Awards in London? Perhaps. While they attended the event as friends, the pair looked like the picture-perfect couple in their Fenty ensembles.

The fashionable friends sat front row together at the Louis Vuitton show during Paris Fashion Week.

Rocky joined Rihanna for the North American portion of her Diamonds world tour.

A true deep cut, Rihanna’s 2012 remix of her song ‘Cockiness (Love It)’ featured A$AP Rocky. The song’s themes? Her dominance over a lover.

Some foreshadowing perhaps?

The pair also performed together at the MTV Video Music Awards.