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Who Has Rob Kardashian Dated? Here's A Timeline Of All His Relationships

When Rob Kardashian was making frequent appearances on Keeping Up With The Kardashians, his love life was splashed across national television. Subsequently, his relationship with Blac Chyna took center stage on his own show, Rob & Chyna, but there's been plenty of relationships he's held down behind the scenes too. While some of his past romances may surprise you, the list of celebs who dated Rob Kardashian is the ultimate walk down memory lane.

Kardashian's relationship with Chyna was arguably his most highly-publicized, and not just because of their show. It was one of his longest, and, at one time, most promising. He and Chyna planned on tying the knot, though their wedding plans fell apart in Feb. 2017. By that time, they already welcomed their daughter Dream into the world and were bound for life as co-parents. Many of Kardashian's relationships are closed chapters, but he and Chyna are still very much part of each other's lives.

Currently, Kardashian is a single man, and has made a point to stay out of the limelight (though, that may change soon). But these former relationships all had fans incredibly invested in the reality star's love life.

2007: Adrienne Bailon

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Kardashian and Bailon dated for two years from 2007 to 2009, but wound up having a dramatic fallout. After the pair called it quits, Kardashian admitted to cheating on the Cheetah Girls member, which contributed to their breakup. Even years later, Bailon says the relationship took a toll on her.

“I will say this, I think anyone who has been in a relationship where they’ve been cheated on or hurt, it affects you," she said during a September 2016 segment of her talk show The Real. “It affected me so much that I made it a conscious decision not to do that to the next person because when you experience the kind of hurt that being cheated on will make you question yourself."

While the pair aren't close in 2020, they are still on good terms despite their rocky past.

2010: Angela Simmons

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Although short-lived, Kardashian and Simmons made headlines with their 2010 relationship. Reports of their romance began surfacing in early March, and they appeared to enjoy each other's company for several months.

While they never directly admitted to dating, Kardashian had the sweetest things to say about Simmons in a May 2010 interview with HipHollywood. "It's good to surround yourself around positive people who have the same upbringing as me and believe in the bible and everything like that," he said.

2012: Rita Ora

Kardashian's relationship with Ora was also short-lived, but wound up being one of his messiest breakups. The pair dated from October to December 2012 before Kardashian unleashed a series of scathing tweets about his former flame. "She cheated on me with nearly 20 dudes while we were together... But I mean 20?!!!!" he tweeted on Dec. 3 but later deleted.

It was two years later when Ora finally addressed the drama herself, telling Power 105.1, “I don't want to talk about this too much because people move onward and upwards. But it was a phase and a moment in my life and now, you know, onward and upwards."

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Rihanna

In August 2012, Kardashian was spotted out on a date with Rihanna where he treated the singer to an adventure-packed night of go-karting in Los Angeles. Sadly, the date didn't lead to more adventures for the pair, but Kardashian did say they had a blast. "It was fun. It was a good night," he said during an appearance on Ryan Seacrest's radio show.

2013: Naza Jafarian

Kardashian and Jafarian enjoyed several global adventures together (they were spotted out in both London and Los Angeles), but the relationship seemingly fizzled out. The two quietly split without any drama or headline-making statements. Jafarian married businessman Folarin Alakija in 2017.

2016: Blac Chyna

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Chyna and Kardashian started dating in January 2016, and their romance quickly caught fire. The fact that Chyna had a rocky history with the Kardashian sisters didn't stop them from pursuing the relationship.

By May 2016, Chyna announced she was pregnant with their first child, and the lovebirds soon announced their plans to get married. Unfortunately, those plans quickly crumbled in Feb. 2017, and the pair had to navigate a messy breakup while raising their new daughter, Dream. Thankfully, they've since found their footing, and are now amicable co-parents.

"I just feel like having a good relationship with the other parent and co-parenting is a healthy type of thing," Chyna told Entertainment Tonight in a May 2019 interview. "It's something that a lot of people need to practice."

2019: Natti Natasha

Kardashian and Latin pop star Natasha enjoyed a very public flirtationship throughout much of 2019, though, neither star explicitly said they were together. They did nothing to hide their flirty comments. One of the sweetest came from Natasha in June.

When Rob posted a pic of Dream on Father’s Day, the singer had the sweetest message, writing, “Happy Father’s Day! You are an excellent father, I know. God bless you. See you soon!” Rob replied, “Thank uuu. See u soon.”

Rob also shamelessly showed his admiration for the singer. "Oh hi," he tweeted on June 3, RTing a steamy photo of Natasha.

In time, their social media interactions slowed, and while these two never had a public fallout, it became apparent they were no longer crushing on each other by the time fall rolled around.