Looking for love. While he might be the most camera-shy member of his famous family, Rob Kardashian has had several high-profile romances over the years — some of which were chronicled on reality TV.
When fans first met the Arthur George founder on Keeping Up With the Kardashians in 2007, he was dating Cheetah Girls alum Adrienne Bailon. Though early episodes of the E! series showed the couple spending time with Kardashian’s family and even moving in together, they called it quits in 2009 after two years together. Bailon later claimed that they split because the California native had been unfaithful during their romance, although she didn’t hold a grudge against him.
“We’ve come such a long way. I think Rob is a great guy. … What’s in the past is in the past, he’s about to be a father. Congratulations to him [and Chyna],” she explained during a September 2016 episode of The Real. “Guys, you have to remember that he was 21 years old at the time. We were super young at the time. This is such old news.”
Following his split from Bailon, Kardashian quietly dated Angela Simmons in 2010 and was in a relationship with Rita Ora for two months in 2012. Though his romance with the singer was short-lived, their split raised eyebrows when the reality TV personality accused Ora of cheating on him with “20 dudes” in a Twitter rant.
“I think people react to things differently and like to express their feelings in certain ways,” she said during an appearance on The Breakfast Club in 2014 when asked about Kardashian’s posts. “I don’t tend to use social media, so when that whole situation happened, silence for me is the biggest form of flattery, and I love to just keep it moving unless I need to say something.”
Kardashian’s most high-profile romance came in January 2016 when Us Weekly confirmed that he had begun dating model Blac Chyna. Their romance quickly heated up, and after a brief split in March of that year, the pair announced that they were engaged and expecting their first child together in May 2016. (Chyna is also the mother of son King Cairo, whom she shares with ex-boyfriend Tyga.)
They welcomed daughter Dream in November 2016 and even starred together on a the E! reality series Rob & Chyna, but after multiple breakups, makeups and public fights, the duo split for good in 2017. “I feel like every person who’s in a long-term relationship, or who is committed to their person, goes through ups and downs,” Chyna told Cosmopolitan South Africa in an interview published in March 2017. “Everything isn’t always going to be peaches and cream. If it is, then it’s fake. I’m in it for the long haul.”
Things took a turn for the worse, however, in July 2017 after Kardashian posted a series of explicit photos of Chyna via Instagram and accused her of cheating on him, doing drugs and neglecting their daughter. In response, the Real Black Chyna star accused him of physical abuse in an emotional Snapchat post.
Keep scrolling to relive all of Rob’s romances over the years:
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Rob Kardashian’s Dating History Over the Years: From Adrienne Bailon to Blac Chyna
Looking for love. While he might be the most camera-shy member of his famous family, Rob Kardashian has had several high-profile romances over the years — some of which were chronicled on reality TV.
When fans first met the Arthur George founder on Keeping Up With the Kardashians in 2007, he was dating Cheetah Girls alum Adrienne Bailon. Though early episodes of the E! series showed the couple spending time with Kardashian's family and even moving in together, they called it quits in 2009 after two years together. Bailon later claimed that they split because the California native had been unfaithful during their romance, although she didn't hold a grudge against him.
"We've come such a long way. I think Rob is a great guy. ... What's in the past is in the past, he's about to be a father. Congratulations to him [and Chyna]," she explained during a September 2016 episode of The Real. "Guys, you have to remember that he was 21 years old at the time. We were super young at the time. This is such old news."
Following his split from Bailon, Kardashian quietly dated Angela Simmons in 2010 and was in a relationship with Rita Ora for two months in 2012. Though his romance with the singer was short-lived, their split raised eyebrows when the reality TV personality accused Ora of cheating on him with "20 dudes" in a Twitter rant.
"I think people react to things differently and like to express their feelings in certain ways," she said during an appearance on The Breakfast Club in 2014 when asked about Kardashian's posts. "I don't tend to use social media, so when that whole situation happened, silence for me is the biggest form of flattery, and I love to just keep it moving unless I need to say something."
Despite the drama, Ora described her ex as "a great dude" and noted that they had both moved on.
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Kardashian's most high-profile romance came in January 2016 when Us Weekly confirmed that he had begun dating model Blac Chyna. Their romance quickly heated up, and after a brief split in March of that year, the pair announced that they were engaged and expecting their first child together in May 2016. (Chyna is also the mother of son King Cairo, whom she shares with ex-boyfriend Tyga.)
They welcomed daughter Dream in November 2016 and even starred together on a the E! reality series Rob & Chyna, but after multiple breakups, makeups and public fights, the duo split for good in 2017. "I feel like every person who's in a long-term relationship, or who is committed to their person, goes through ups and downs," Chyna told Cosmopolitan South Africa in an interview published in March 2017. "Everything isn't always going to be peaches and cream. If it is, then it's fake. I'm in it for the long haul."
Things took a turn for the worse, however, in July 2017 after Kardashian posted a series of explicit photos of Chyna via Instagram and accused her of cheating on him, doing drugs and neglecting their daughter. In response, the Real Black Chyna star accused him of physical abuse in an emotional Snapchat post.
Later that year, she filed a defamation lawsuit against Kardashian and his family — specifically Kris Jenner, Khloé Kardashian, Kim Kardashianand Kylie Jenner — claiming that they convinced E! to cancel Rob & Chyna. In May 2022, a jury sided with the famous family in the case, and Chyna was not awarded damages. She also sued Rob for allegedly posting revenge porn after their split and the pair reached a settlement in June 2022.
Amid all of the drama surrounding his breakup with Chyna and their difficult coparenting relationship, Rob took a step back from the spotlight to focus on his health and wellness journey. In March 2022, a source exclusively told Us that he had begun dating again. "He’s in good shape and is happy with how far he’s come," the insider said at the time. “He’s dating but is also private about that. He’s never going to stop caring about his mental health and overall health. It’s important to him so he can be the best father to Dream."
Keep scrolling to relive all of Rob's romances over the years:
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Adrienne Bailon
The entrepreneur dated former Bailon for two years before they called it quits in 2009. Their relationship — and cheating scandal — played out on Keeping Up With the Kardashians. "Rob and I, when we broke up, we pretty much were like, 'We're not going to talk about it,'" the Disney Channel alum recalled during a July 2013 episode of The Real. "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." Bailon later revealed that she eventually wrote her ex an email from her fake boyfriend to get him to stop calling her in an attempt to reconcile.
Three years later, she told her cohosts on The Real that she had moved on and was no longer angry with Kardashian. "We've come such a long way. I think Rob is a great guy. ... What's in the past is in the past," Bailon said at the time.
Bailon married Christian music artist Israel Houghton in November 2016, and they welcomed son Ever via surrogate in August 2022.
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Angela Simmons
Following his emotional split from Bailon, the Keeping Up With the Kardashians star had a fling with the Growing Up Hip Hop star for a few months in 2010. The pair attended Lakers games and were frequently spotted getting pedicures together.
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Rita Ora
Rob dated singer and actress Rita Ora for two months in 2012 before accusing her of cheating on him with “20 dudes.” After he bashed Ora on Twitter, his sister Khloé intervened and tweeted: “Rob be nice kiddddd.”
Two years later, Ora told Power 105.1's The Breakfast Club that she didn’t want to discuss their split. "It was a phase and a moment in my life,” she said. “You know, onward and upwards." By December 2020, the England native had nothing but fond — if vague — memories of their time together. “Oh, I forgot about that,” she told The Sunday Times about dating Kardashian. "It was very short-lived. I was so young. It was fun. It was very, very fun, I guess. That’s all I remember."
Their breakup contributed to Kardashian’s downward spiral into depression, which would come to light in 2016. Ora married Taika Waititi in 2022.
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Rihanna
The business owner briefly romanced Rihanna in August 2012 following his dramatic split from Ora. The pair’s first date included an action-packed go-karting day at Racer's Edge Indoor Karting in Burbank, California, before partying at L.A.'s Playhouse nightclub later that evening. However, things between them soon fizzled out and their romance was over by fall of that year.
The Rob & Chyna star met the British singer through one of his friends and began dating her in March 2013. The pair were spotted out on several dates in Los Angeles and in London.
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Blac Chyna
Rob and Blac Chyna shocked the world when they revealed their romance via social media in January 2016. The couple began dating while his youngest sister, Kylie, was still seeing Chyna's ex-boyfriend Tyga. Despite the drama, Rob popped the question in April 2016 and announced that they were expecting a baby girl one month later. After a series of intense (and public) fights, the duo called off their engagement in December 2016, one month after welcoming daughter Dream. They split for good in early 2017.
Though he initially credited Chyna with helping him with his depression, Rob claimed in April 2022 that he was at “the worst place in my entire life, at my weakest, lowest point” when they were together. "She was the one person who brought me in at my lowest point. So I ignored her bad behavior toward my family," he said in court. "I wasn’t thinking about that stuff. My mind was just in a completely different place. It wasn’t real love."
The twosome are in the midst of an ongoing child support battle, after Chyna claimed in March 2022 that she had not received any money from either Rob or Tyga. “I pay 37k a year for my daughter’s school. I handle every single medical expense. I pay for all her extracurricular activities. I have my daughter from Tuesday-Saturday,” he fired back via Instagram, per The Shade Room. “Why would I pay child support lol?”
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Mehgan James
In May 2017, Us Weekly confirmed that Kardashian had moved on from his on-again, off-again relationship with Blac Chyna and had started dating Bad Girls Club alum James. “Rob has been happy and understands that he and Chyna are not a match,” a source told Us following the news of his new romance. “Both of them do better without each other.”
Just one month later, however, Rob seemingly denied that he was seeing the reality star. “Wait reading online about some chick I’m dating Megan something. Not true never even met her or heard of her before,” he wrote via Twitter at the time. James, for her part, retweeted the post and added, "Although I’ve been advised not to say anything , I will say, I’m only ‘Megan something.’ I don’t control the media but we all know who does. I'm just as confused as everyone else."
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Alexis Skyy
The former E! personality was linked to the Love & Hip Hop star in January 2019, even declaring her to be his "WCW" on Snapchat just days after she and Chyna allegedly got into a physical altercation at a private event. “I’ve been wanting you for so long," he wrote at the time, later sharing a Snapchat video of him and Skyy having dinner together. “Me and Alexis known each other for 5 years so stop with that,” he wrote via Twitter at the time, shutting down rumors that he and Skyy were attempting to upset Chyna with their date night. “Damn i was just trying to eat some good food.”
