Before Rihanna A$AP Rocky Dated Models, Another Rapper, and Two Sisters

After months of speculation that Rihanna was expecting her first child with rapper A$AP Rocky, the pair confirmed RiRi’s pregnancy by showing off her baby bump during a stroll through New York City in late January. Rihanna is a very famous name but many fans don’t know a ton about her boyfriend.

Here’s a little more about A$AP Rocky including the other high-profile women he dated before the Fenty founder.

Photo of Rihanna and ASAP Rocky on the carpet at 2021 Costume Institute Benefit
Photo of Rihanna and A$AP Rocky on the carpet at 2021 Costume Institute Benefit | Sean Zanni/Patrick McMullan via Getty Images

Iggy Azalea

A$AP Rocky was born Rakim Athelaston Mayers and is known for songs like “Praise the Lord (Da Shine),” “Sundress,” and “F***** Problems.” His first single to receive airplay was “Peso” in 2011. That same year the hip-hop artist began dating another rapper. Iggy Azalea and Rocky were together for about a year and during that time the “Fancy” hitmaker got a tattoo on her fingers that read: “Love.Live.A$AP.”

In 2012 she told Vibe: “I love him … We have our own thing going on and I’m not the only one that [got the tattoos]. I’ll tell you that. I’m just the only one with it on my fingers!”

When they called it quits, Azalea had the ink of his name crossed out.

Iggy Azalea performing at Shoreline Amphitheatre in California
Iggy Azalea performing at Shoreline Amphitheatre in California | Steve Jennings/WireImage

Rita Ora

After Azalea, Rocky was linked to British songbird Rita Ora. But things between them were complicated and not exactly clear to the public. Rocky was criticized for some vulgar lyrics about Ora in his track “Better Things.” He then offered an explanation for his comments.

“I just want to clarify, this isn’t me saying, people don’t go listen to Rita Ora or she’s an ugly person or nothing,” he said (per Rolling Out). “I’m not saying she’s a terrible person. I’m just saying that when I was in a relationship and I did things with her that I wasn’t supposed to do, she had a big mouth.”

Ora fired back in an interview with Glamour and claimed that she never dated the rapper. “Don’t disregard what I’ve done with my career because of someone that I was dating — if I was even dating that person, which I wasn’t,” she said via the Evening Standard, before adding: “Let’s be very clear on that. I was not.”

Rapper A$AP Rocky and singer Rita Ora arrive at the 2012 MTV Video Music Awards
Rapper A$AP Rocky and singer Rita Ora arrive at the 2012 MTV Video Music Awards | Steve Granitz/WireImage

Chanel Iman

In 2013, Rocky and Victoria’s Secret model Chanel Iman were an item.

The couple appeared arm in arm at a few events together and reportedly got engaged. But before they walked down the aisle together, they decided to call off their engagement citing their busy schedules.

Rocky later said that the reason for their breakup was because “I knew that she deserves better than me.”

A$AP Rocky and Chanel Iman entering the Charles James Beyond Fashion Costume Institute Gala
A$AP Rocky and Chanel Iman entering the Charles James Beyond Fashion Costume Institute Gala | Ray Tamarra/GC Images

Kendall and Kylie Jenner

The “Out of This World” artist was linked to reality TV star and supermodel Kendall Jenner in 2016.

They two tried to keep things under wraps for a while but were eventually spotted getting cozy on multiple occasions in Paris, New York, Miami, and Los Angeles.

Kendall Jenner and A$AP Rocky at a flea market together in 2017
Kendall Jenner and A$AP Rocky at a flea market together in 2017 | Pierre Suu/GC Images

In November 2015, months before romance rumors about Kendall and Rocky swirled, the rapper was thought to be involved with the model’s younger sister Kylie Jenner.

However, Rocky and the makeup mogul never bothered to confirm or deny those reports.

RELATED: A$AP Rocky Talks Fatherhood: Knows He’s Going to ‘Have a Very Fly Child’