Rob Kardashian’s best-documented public relationships were with Adrienne Bailon, Angela Simmons, Rita Ora and Blac Chyna. The accounts range from a relationship reported to have lasted about two years to brief dating links; they are not all equivalent partnerships, and no public list can verify his entire private history.
Who has Rob Kardashian dated?
Entertainment coverage has linked Kardashian to four women: Adrienne Bailon, Angela Simmons, Rita Ora and Blac Chyna. Us Weekly describes the first as a longer relationship, Simmons as a fling, Ora as a two-month relationship and Chyna as a highly public relationship that included an engagement and their daughter, Dream. These are publicly reported accounts, not a complete or independently verified record of his private life. Us Weekly’s relationship timeline covers the reported connections.
His reported relationships, in order
Adrienne Bailon: 2007–2009
Us Weekly dates Bailon and Kardashian’s relationship to 2007–2009, roughly two years. They were dating when Kardashian first appeared on Keeping Up with the Kardashians, and parts of their relationship played out on the show. Bailon later said infidelity was part of the breakup; that is her account, not an independently established finding.
In 2016, Bailon reflected on how young they had been when they dated, saying, “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.” She also said, “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.” The comments are quoted in Us Weekly’s retrospective.
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Angela Simmons: a brief link in 2010
Us Weekly characterizes Kardashian’s reported 2010 connection with Simmons as a fling lasting a few months, rather than a long-term relationship. The outlet notes that they attended Lakers games and were seen getting pedicures. The reporting supports describing this as a brief romantic link, not an established partnership.
Rita Ora: a reported two-month relationship in 2012
Us Weekly reports that Kardashian and Ora dated for two months in 2012. During their breakup, Kardashian accused Ora of cheating in a Twitter post. That was his allegation, not a verified fact. In a 2014 Breakfast Club appearance, Ora said she did not generally use social media and preferred to move on, according to Us Weekly.
Blac Chyna: a public relationship, engagement and co-parenting
Kardashian and Chyna confirmed they were dating on January 25, 2016. They announced their engagement in April, confirmed a pregnancy in May and welcomed their daughter, Dream, on November 10, 2016. The milestone dates appear in E! News’s timeline, published in 2016 and updated in 2017.
The couple also appeared together on Rob & Chyna. Us Weekly reports that they split in 2017 after breakups and reconciliations. Their later legal disputes are a separate part of the public record: the outlet says a defamation suit brought by Chyna against Kardashian and family members ended in a jury verdict for the family, with no damages awarded, in May 2022; a separate lawsuit concerning explicit images settled in June 2022. Those outcomes should not be treated as resolving every disputed allegation. The relationship and legal timeline is summarized by Us Weekly.
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What Kardashian said about dating after Dream’s birth
In an interview excerpt published July 16, 2025, Kardashian said he had dated since Dream was born but had not pursued a serious relationship. “Of course, I’ve dated and stuff, but I’ve never gotten serious or wanted to,” he said on Khloe in Wonder Land. He also said he preferred not to go on dates. Just Jared published the comments that day. They describe what he said in 2025; they do not establish his relationship status in October 2026.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.How to read the public record
The most useful distinction is between what the reporting actually calls each connection and how much of it was publicly documented. Bailon is reported as a roughly two-year relationship; Simmons as a months-long fling; Ora as a two-month relationship; and Chyna as a public engagement and co-parenting relationship. The dates and durations come from entertainment-publisher timelines, not a comprehensive account of Kardashian’s private life.
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