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.
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 Kardashian and 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: