A Complete History Of Rob Kardashian's Girlfriends Throughout The Years

Being a part of one of the world's most famous families, it's safe to say that Rob Kardashian has had his pick of the litter when comes to the ladies. From dating superstars from Blac Chyna to Rihanna, the Keeping Up With The Kardashians star has romanced a medley of beautiful women throughout the years. Keep scrolling to get a refresher on who Rob has loved and even lost.

Rob dated former Cheetah Girl member and current The Real cohost Adrienne Bailon from 2007 to 2009. Their relationship was fully documented on KUWTK, but they split after he cheated on her.

The 31-year-old had a very tumultuous relationship with ex and baby mama Blac Chyna. They started dating in January 2016 and even got engaged in April of that year. But after a sequence of fights and drama and an eventual breakup, the two welcomed their daughter, Dream, in November 2016.

Most recently, he revealed on social media that he had a crush on Love & Hip Hop: New York star Alexis Skyy. He posted a photo of her and added the caption, “My WCW Woman Crush Wednesday…I’ve been wanting you for so long.” He also included a series of heart emojis. Alexis was also recently in a feud with Chyna after claiming the mother of two threw a drink at her at a party.

Rita Ora and Rob dated for a brief two months in 2012. He accused her of cheating on him and then went on to bash her on Twitter. But in 2018, when Rita's song, "Girls" got major major backlash, Rob defended her.

The reality star moved swiftly to date Rihanna after his breakup with Rita in 2012. The two went go-karting and then to a nightclub for their first date. Their fling was short-lived and Rihanna went back to dating ex Chris Brown soon after.

After Adrienne and Rob split, he had a small fling with Growing Up Hip Hop star Angela Simmons for a few months back in 2010. Their dates usually including getting mani-pedis and attending basketball games.

After breaking it off with Chyna, Rob went on to romance Bad Girls Club star Meghan James in May 2017. But their relationship was nothing more than just some heavy flirtation.

Rob made a rare appearance for the first time in months in November 2019 when he stepped out to celebrate sister Kendall Jenner's birthday. He was spotted sharing PDA with younger sister Kylie Jenner's best friend, Stassie Karanikolaou. The pair was seen giggling and staying close by to each other. The Halfway Dead designer even placed his hand around the 22-year-old’s waist.