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 couple confirmed RiRi’s pregnancy by showing off her baby bump while out for a walk in New York City in late January. Rihanna is a very famous name but many fans don’t know much 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 A$AP Rocky on the carpet at the 2021 Costume Institute Benefit | Sean Zanni/Patrick McMullan via Getty Images

Iggy Azalea

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

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

When they called out to him, Azalea had her name crossed out in ink.

Iggy Azalea performing at the Shoreline Amphitheater in California

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

Rita Ora

After Azalea, Rocky was linked to British singer 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 remarks.

“I just want to clarify, it’s not me saying, people don’t 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 when I was in a relationship and doing things with her that I wasn’t supposed to do, she was a big mouth.

Ora fired back in an interview with Glamor and claimed she had never dated the rapper. “Don’t discount what I did with my career because of someone 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 this. I wasn’t.”

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 was 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 the reason for their breakup was because “I knew she deserved better than me”.

A$AP Rocky and Chanel Iman Attend Charles James Beyond Fashion Costume Institute Gala

A$AP Rocky and Chanel Iman Attend 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 model Kendall Jenner in 2016.

They both 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 together at a flea market in 2017

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

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

However, Rocky and the makeup mogul never bothered to confirm or deny this information.

RELATED: A$AP Rocky Opens Up About Fatherhood: Knows He’ll ‘Have A Very Flying Child’

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