ASAP Rocky Dating History: Rihanna, Kendall Jenner and More

Rapper A$AP Rocky is in the throes of a blossoming romance with Rihanna at the moment, but his dating history certainly proves that the New York City native doesn’t have a type.

Prior to his romance with the “We Found Love” singer, the A$AP Mob crew member dated Kendall Jenner for more than a year, from July 2016 to August 2017. The pair were pals long before things turned romantic, and they sparked dating rumors after being spotted together on several occasions in 2016. They famously attended the 2017 Met Gala together alongside Kenny’s younger sister, Kylie Jenner, and her off-again, on-again boyfriend, Travis Scott.

RiRi and A$AP sparked romance rumors in January 2020, following her split from boyfriend of three years Hassan Jameel. The couple made their red carpet debut at the Fashion Awards at London’s Royal Albert Hall one month prior, but fans were unsure if the pair were just friends at the time.

In December 2020, an insider exclusively told Life & Style that the artists, who were in the early stages of dating at the time, “have a ton in common,” which was making their newfound romance thrive. “They’re creative, very family-oriented, and they make each other laugh,” the source added. “The best part is that they were friends first, which helps. It’s the basis for a great romantic relationship.”

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In May 2021, the All Smiles artist opened up about his relationship with the Barbadian native, calling her “the love of my life” and “my lady.” He also noted that he enjoys being in a committed relationship — and that it’s “so much better” than playing the field. “So much better when you got The One,” A$AP gushed to GQ. “She amounts to probably, like, a million of the other ones. I think when you know, you know. She’s The One.”

The A-list performer even revealed that his girlfriend — who hasn’t released music since her record Anti in 2016 — “absolutely” influenced his new music. He said, “I think it’s important to have somebody that you can bounce those creative juices and ideas off of.”

Scroll through the gallery below to see all of A$AP Rocky’s girlfriends, past and present, including Kendall and Rihanna.

Rita Ora

In 2015, the performer rapped about the singer’s “big mouth” on his track “Better Things,” which also included graphic descriptions of their intimate encounters. The pair allegedly hooked up while he was in a relationship.

He later addressed the lyrics. “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 explained during an interview, according to Capitol Xtra. “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.”

The “Body on Me” singer clapped back and called the comments “tasteless” in an interview with Glamour. “It’s not about me. It’s about women,” she said. “Disrespecting women. It’s not cool. There’s more to a person than who you’re dating … 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. Let’s be very clear on that. I was not. And nor will I ever.”

Iggy Azalea

A$AP and the Australian rapper were romantically linked in 2011. They got tattooed for each other while they were together. “I love him and that’s all there is to it. We have our own thing going on and I’m not the only one that [got the tattoos],” the “Fancy” singer previously revealed about their ink. “I’ll tell you that. I’m just the only one with it on my fingers!”

The pair split in 2012, and the “Work” rapper had her tattoo removed in 2015.