Robert Arthur Kardashian, known widely as Rob Kardashian, has navigated a complex and often public romantic history, heavily influenced by his family's pervasive presence in reality television. As the only son of the late Robert Kardashian Sr. and Kris Jenner, his relationships have frequently been under intense media scrutiny, ranging from early, on-screen romances to highly publicized engagements and dramatic separations. Despite his increasing preference for a private life in recent years, his past relationships have left an indelible mark on his public narrative.
One of Rob Kardashian's earliest and most significant public relationships was with actress and singer Adrienne Bailon. Dating from 2007 to 2009, their romance played out prominently on the early seasons of Keeping Up With the Kardashians. The couple's journey, from their initial connection to their eventual split, was a focal point of the show, offering viewers an intimate look into their lives. Their relationship was characterized by young love and the pressures of newfound fame.
The relationship with Adrienne Bailon ultimately concluded amidst public revelations of infidelity on Rob's part. Adrienne later reflected on the challenges of dating a Kardashian, stating in a 2014 interview, > "To be stuck with that Kardashian label, that was so hurtful to me and to my career." Despite the dramatic breakup, Bailon has maintained a friendly relationship with the Kardashian family over the years, even attending Khloé Kardashian's wedding to Lamar Odom as a bridesmaid.
Following his split from Bailon, Rob Kardashian had a brief, quiet romance with Angela Simmons in 2010. The daughter of Run-DMC's Rev. Run, Simmons and Kardashian were linked for a few months, often spotted attending Lakers games and engaging in casual outings. Their relationship, while not as extensively documented as his previous one, was acknowledged in media reports, indicating a low-key connection that eventually fizzled out.
In 2012, Rob Kardashian entered into a short-lived but highly publicized relationship with British singer Rita Ora. Their romance spanned approximately two months and garnered significant media attention due to both their public profiles. However, the relationship ended controversially, with Kardashian taking to Twitter to accuse Ora of cheating on him with multiple men. His public accusations led to a social media firestorm, prompting his sister Khloé Kardashian to intervene and publicly advise him to "be nice."
After the tumultuous end with Rita Ora, Kardashian's dating life became less public for a period, though he was briefly linked to other personalities. He reportedly dated actress and model Daphne Joy in October 2013. This connection was short-lived and largely remained out of the intense public spotlight that had characterized his earlier relationships. Similarly, he was linked to Instagram model Amina Blue from 2014 to 2015, a relationship that also maintained a relatively low profile compared to his more high-profile romances.
The most significant and tumultuous chapter in Rob Kardashian's romantic history began in January 2016 when he went public with model Blac Chyna. Their relationship immediately sparked widespread controversy and fascination, largely due to Chyna's prior connections to the Kardashian-Jenner family. Chyna shared a son, King Cairo Stevenson, with rapper Tyga, who was dating Rob's half-sister Kylie Jenner at the time. This complex web of relationships created immediate tension within the family, though Rob's mother and sisters eventually warmed to the relationship, noting Chyna's positive impact on Rob's well-being.
The relationship between Rob Kardashian and Blac Chyna escalated quickly. By April 2016, just three months after going public, the couple announced their engagement, surprising many. Their whirlwind romance became the subject of their own reality series, Rob & Chyna, which premiered in September 2016 and chronicled their journey, including their preparations for parenthood. On November 10, 2016, they welcomed their daughter, Dream Renée Kardashian, marking a significant milestone in their relationship.
Despite the birth of their child and their shared reality show, the relationship between Rob Kardashian and Blac Chyna was plagued by drama and public disputes. Their engagement ended in 2017, and their separation was marked by a series of highly volatile public exchanges, including accusations of infidelity, abuse, and the unauthorized sharing of explicit images by Rob. Blac Chyna subsequently filed a defamation lawsuit against Rob and his family, alleging that they had conspired to cancel their reality show and damage her career. While the lawsuit brought further public scrutiny, the former couple eventually reached an agreement for joint custody of their daughter, Dream, in September 2017.
Since the highly public and dramatic end of his relationship with Blac Chyna, Rob Kardashian has largely retreated from the public eye, prioritizing his privacy and focusing on co-parenting his daughter, Dream. While there have been sporadic rumors and reports of him dating, such as a "public flirtationship" with Latin pop star Natasha in 2019, these have not led to confirmed, long-term public relationships. He has made fewer appearances on Keeping Up With the Kardashians and its spin-offs, preferring a more low-key lifestyle. His current relationship status remains private, with his primary focus appearing to be on his role as a father and his personal well-being, a significant shift from the highly public romantic chapters of his past.