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Here’s a Rundown of Rob Kardashian’s High-Profile Dating History

Celebrities
Jordan Williams
Author: Jordan Williams
8 min.read
Rob Kardashian's Dating History Over the Years From Adrienne Bailon toBlac Chyna

Like any other famous Kardashian family member, Rob Kardashian’s love life and dating history didn’t escape the cameras. For those who haven’t been religiously keeping up with them, you will definitely find the names of celebrities he’d been with very surprising. In fact, you’d probably say, “They dated?!”

We wouldn’t want to keep the suspense for so long, so let’s roll it. 

Adrienne Bailon (2007 – 2009)

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Cheetah Girls alum Adrienne Bailon was Rob’s first girlfriend in the E! series. The two started dating in 2007, and for the most part, it did look like they would be each other’s endgame. Unfortunately, they weren’t. They called it quits two years into dating, and it was because of Rob’s cheating scandal. 

In an episode of The Real aired in July 2013, she shared that it was a mutual agreement between her and Rob to not talk about what had happened. “It was private. … And I think people would think that because I was cheated on, I would want to go out there and say, ‘He cheated on me!’ But I was embarrassed,” she confessed. 

After they broke up, Rob attempted to reconcile with Bailon multiple times, so she created a fake boyfriend to “write” an email just to get him to stop. They eventually both moved on, and years later, Bailon said that she was no longer angry at Rob and that they had come a long way. 

“What’s in the past is in the past.” She even remained close with the Kardashian sisters and attended Khloe’s wedding to Lamar Odom as a bridesmaid.

She is now a wife to husband and Christian music artist Israel Houghton and a mom to their son Ever. 

Angela Simmons (2010)

A year after his emotional breakup with Bailon, Rob started dating Run House’s Angela Simmons. 

The two were often spotted together attending Lakers games and getting pedicures. While it was a short-lived relationship, as the two only dated for a few months, their romance definitely caught headlines. However, Rob never directly admitted to dating Simmons.

In an interview with HipHollywood, he called her his best friend, saying that it was good to have someone positive and who had the same upbringing as him (which was someone who believed in the bible and everything like that). 

Simmons announced last January 1, 2023, through an Instagram post, that she and rapper Yo Gotti are together.

Rita Ora (2012)

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Following Simmons, the reality TV star dated singer-songwriter and actress Rita Ora. It was his shortest relationship (lasting only two months) and also the messiest. 

In a now-deleted tweet posted by Rob, he said they broke up because Ora cheated on him with not just one or two but “nearly 20 dudes.” The singer didn’t engage her former flame any further and only talked about the drama two years after the fact.

While speaking with Power 105.1’s The Breakfast Club, she said she didn’t want to discuss their split. It was a phase and moment in her life; she was all about moving onwards and upwards. And despite their bitter end, she confessed that it was a very fun time in her life. 

Ora is now married to famed director Taika Waititi.  

Rihanna (2012)

After Ora, Rob went to briefly date another big name: singer and Fenty founder Rihanna.

The two spent their first date in Burbank, California, enjoying an action-packed go-karting adventure at Racer’s Edge Indoor Karting. Later that night, they partied at LA’s Playhouse nightclub. Sadly, that romance quickly fizzled out, and according to Us, they were already over by the fall of that year. 

Rihanna is currently dating A$AP Rocky. They welcomed their son Noah Mayers in 2022, and another one is on the way!

Naza Jafarian (2013)

After things with Ora didn’t work out, Rob moved on to another British beauty, Naza Jafarian. 

According to an insider, Jafarian, a model born in Iran and raised in London, was introduced to Rob by his best friend. They started dating and were sighted in Los Angeles and London. The two dated for quite some time, but just like all the others (after Bailon), it ended before it even started. 

Jafarian is married to Nigerian entrepreneur Folarin Alakija, sharing two kids together.

Blac Chyna (2016 – 2017)

It took quite a few years before Rob started dating again. And when he did, he wasted no time taking it to the next level. 

Rob and model and actress Blac Chyna revealed their relationship on social media back in 2016. Weirdly enough, the two started dating while Kylie Jenner was also dating Chyna’s ex, Tyga. 

However, that “awkwardness” didn’t prevent Rob from asking Chyna to marry him. She said yes, and a month later, they announced that they were expecting a baby girl. 

Their happiness as newly-engaged and soon-to-be parents soon died out. They also had a series of fights that were intense and very public. Then just a month after they welcomed their daughter, Dream, they called off their wedding engagement and concluded everything a few months later. 

Then came the revelation of more drama (specifically, dirty laundry). In an interview in 2022, Rob said he was at the worst place in his entire life during their relationship, which opposed his initial claim that Chyna helped with his depression. Moreover, he highlighted that she brought him to his lowest point. 

“So I ignored her bad behavior toward my family.” Then he continued, “I wasn’t thinking about that stuff. My mind was just in a completely different place. It wasn’t real love.” Despite many obstacles between them, including a contentious child support battle, the two are now good and have been co-parenting. 

Blac Chyna is definitely more at peace and happy now, especially with her new boyfriend, rapper Twin Hector. 

Mehgan James (2017)

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This relationship between Rob and Bad Girls Club alum Mehgan James may or may not have happened at all. According to a source by Us, the Kardashian moved on from Chyna with James shortly after their engagement was called off. However, Rob denied dating whom he called in a tweet “Megan something,” and James retweeted the post saying that she was just as confused with the news. 

Alexis Skyy (2019)

Rob’s romance with Love & HipHop star Alexis Skyy looked like it was five years in the making.

In a Snapchat video of him and Skyy sharing a lovely dinner, he wrote that he had wanted her for so long. They’ve known each other for five years at that point. That said, their relationship wasn’t really going to grab any headlines until Blac Chyna entered the scene. 

Apparently, the two had a physical altercation at a private event in LA. Skyy claimed that the fight broke out after Rob’s ex allegedly threw a drink at her and demanded that she remove herself from the VIP section. So, she charged at her but was held back by guests. 

After that, there wasn’t any news about her and Rob. By the looks of it, she doesn’t have anything going on with her love life at the moment. 

Natti Natasha (2019)

We’ll probably never know if Rob and Latina pop singer Natti Natasha ever made it out of their social media flirting. What we do know is that if they did, they were long past an item.

Natasha is engaged to her manager Raphy Pina (currently in prison), and they share a daughter named Viva Isabelle.

Aileen Gisselle (2020)

As the years go by, Rob’s dating life has become increasingly more private. Thanks to Giselle’s social media activity, fans caught a whiff that he and Instagram model Aileen Gisselle probably dated. 

First, Gisselle shared a clip of Rob with hearts all around his face. Second, she posted a photo of her wearing Rob’s Arthur George socks with the print reading “My boyfriend.”

There had been no public confirmation or denial of the news, and their “thing” was eventually forgotten. Gisselle also switched her Instagram to private.

Liana Levi (2022)

Rob Kardashian and Forma Pilates founder Liana Levi haven’t confirmed whether they’re dating or not. We’ll just have to tune in to see if they really are and if she’s indeed the last to be listed in his dating history. 

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