Rob Kardashian’s Biggest Relationship Scandals Exposed! — Inside His Breakup With Adrienne Bailon, Shocking Romance With Blac Chyna And More!

Rob Kardashian hasn’t always been the luckiest man when it comes to his love life! But the reality TV star and beloved Kardashian family member has continued his search for his perfect lady through all of his heartbreak and relationship drama. And from his whirlwind romance with Blac Chyna to his messy split from his first love Adrienne Bailon, we’ve gathered all of Rob’s biggest relationship scandals ever!

Rob’s first extremely public romance was with his ex Bailon! The two stole viewers hearts as they gushed over each other during their appearances on Keeping Up with the Kardashians. And Rob openly admitted that he was falling deep in love with the singer and actress!  But their bliss turned into breakup madness when Bailon found out that Rob had cheated on her. Rob confessed to cheating on Bailon during an episode of KUWTK and even documented his attempts to reconcile with her on the show. However, Bailon wasn’t having it and the two eventually parted ways for good.

Rob eventually moved on to another singer — Rita Ora! But their relationship didn’t last long, ending in a nasty feud between the two! Following their split, Kardashian took to his Twitter to seemingly blast Ora in a heated rant where he accused an ex of cheating on him “with 20 men!” He later tweeted that he never specifically called out Ora in the rant. "Just so we clear I never once mentioned 'Rita Ora' in any of my tweets or even used the word 'whore' and I never would. I Respect Women," Rob tweeted. But his followers remained convinced that the post was likely directed at his former flame!

Rob also briefly appeared to set his eyes on another lady — his sister Khloe Kardashian’s best friend Malika Haqq. The two were often caught flirting on Khloe and Lamar. And they even attempted to fool Khloe into thinking that they were an item during one episode of the show. But the two never officially began dating!

Rob eventually withdrew from the spotlight following his successful run on Dancing with the Stars, with the buzz around his love life quickly falling off as he dealt with some serious personal issues. But the relationship drama was reignited in 2014 when Bailon blasted Rob and his family in an interview with Latina! Speaking to the mag, she called out Rob for cheating on her during their relationship. She also claimed that appearing on KUWTK wasn’t the best decision for her as an actress and TV personality and opened up about the fallout over their split! "It's common knowledge that he cheated on me," Bailon said. "It always bothered me that people were like, 'Pero, why couldn’t you forgive him?'" She then continued, "Why are women always the ones who have to forgive? If you cheated on a man, he would be like, 'You're disgusting, and I want nothing to do with you.' But women, we're supposed to be like, 'He messed up. He made a mistake.'"

Rob’s family members rallied around him after the interview was released, with both Kim Kardashian and Khloe dissing Bailon on Twitter over her comments. But Bailon also took digs at Rob on her talk show The Real and when she did a special with Extra on her procedure to get her tattoo of Rob’s name removed from her body!

It seemed like Bailon was completely cut off from the Kardashian crew! But when she called off her engagement to her ex Lenny Santiago in September 2015, talk began to spread that Bailon and Rob had reconciled! Bailon eventually knocked the rumors. But she was later photographed hanging out with Rob’s sisters Kourtney Kardashian and Kylie Jenner in February 2016!

But lucky for Rob, he ultimately found his true match in none other than Blac Chyna! Chyna is the ex-fiancée of his sister Kylie’s boyfriend, Tyga, and the best friend to his brother-in-law Kanye West’s ex Amber Rose. But that didn’t keep Rob from falling head over heels for the Chyna in a matter of a few months!

Rob came out of social media hiding to announce his relationship with Chyna, with Kardashian even joining Snapchat to share all the updates on their romance! Chyna was immediately credited for helping Rob drop several pounds after his lengthy weight battle. And Rob even drove several hours to pick Chyna up from jail after she was arrested for public intoxication at an Austin, Texas, airport!