When it comes to the Kardashian-Jenner family, it’s usually the females of the family who have relationships that get constantly talked about and discussed in the media. Kim Kardashian"s marriage to Kanye West is a huge topic of conversation and so was Kourtney Kardashian"s on and off relationship with Scott Disick for so many years.
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Kylie Jenner‘s relationships with Tyga and Travis Scott always made headlines and the whole entire world knows about Khloe Kardashian"s on and off relationship with Tristan Thompson riddled with scandal. Rob Kardashian has been embroiled in interesting romantic situations of his own over the years and is currently dating someone new!
10 Adrienne Bailon: 2007 - 2009
From 2007 to 2009, Rob Kardashian was in a relationship with Adrienne Bailon. Bits and pieces of the relationship we’re showcased on Keeping Up With the Kardashians in the earlier seasons of the show. She was busy starring in the cheetah girls on Disney Channel at the time! Unfortunately, due to infidelity on his part (which he openly revealed on the show), their relationship came to an end and they both knew that they needed to move on. According to the show, this particular breakup was pretty hard on him.
9 Angela Simmons: 2010
In 2010, Rob Kardashian was romantically linked to Angela Simmons from Run"s House. They were spotted out and about at sporting events and on cute dates. They were even spotted getting their nails done together at one point. Their relationship was not built to last though. They only stayed together for a few months.
8 Rita Ora: 2012
Fast forward from 2010 to 2012 and you’ll find out that Rob Kardashian was also in a 2-month relationship with Rita Ora. Rita Ora is an incredible singer who released the song “R.I.P." back in 2012. It was a huge hit at the time and she has still steadily been releasing music since then. She did not have an amicable breakup with Rob Kardashian though. He accused her of cheating on him on Twitter and she never publicly spoke out about what happened in interviews.
7 Rihanna: 2012
As random and weird as it might sound, Rob Kardashian and Rihanna actually briefly got together in August 2012. They were photographed going on dates at the time and it seemed like they were just living it up and enjoying themselves.
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It wasn’t built to last and it fizzled out very quickly but the fact that it ever even happened in the first place is mine boggling. They seem like such different people! They must’ve had at least a few things in common.
6 Naza Jafarian: 2013
In March 2013, Rob Kardashian started dating a British singer named Naza Jafarian. They met because they were introduced to each other through mutual friends. Paparazzi spotted them out on dates together in the United Kingdom in the United States which means that they were doing quite a bit of traveling together. She is definitely a beauty and the reason for their break up is not public.
5 Blac Chyna: 2016 - 2017
Pretty much everyone knows by now that the relationship between Rob Kardashian and Blac Chyna started off amazingly and turned toxic pretty quickly. It seemED like the two really had each other"s backs and were excited to show each other off.
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They were especially excited to announce their pregnancy to the world when they found out that she was pregnant with their daughter, Dream Kardashian. In reality, their issues ended up becoming too much for them to overcome and a lot of their toxic battles played out on the reality TV show Rob & Chyna.
4 Mehgan James: 2017
In 2017, rob Kardashian started dating Megan James, a former reality TV star from Bad Girls Club. The details of their relationship were not ever made public so no one knows exactly what went south between the two while they were dating. Along with her reality TV career, she’s also appeared in a few other movies in the past.
3 Alexis Skyy: 2019
Rob Kardashian posted a picture of Alexis Skyy on Twitter calling her his “Woman Crush Wednesday” in January 2019. He is not shy to let the women he is interested in know exactly how he is feeling which is actually an incredible character trait of his. Alexis Skyy posted a picture of herself having dinner with Kris Jenner after Rob flirted with her on social media proving that the two probably started a fling. It didn’t last though.
2 Natti Natasha: 2019
In 2019, Rob Kardashian and Natti Natasha did quite a bit of flirting on social media causing a lot of people to speculate if they had started a relationship with each other or not. Both individuals refused to confirm or deny the rumors to the public so no one knows for sure if they ever actually dated or not. What we actually do know now is that they are no longer a thing.
1 Aileen Gisselle: 2020
As of August 2020, Aileen Gisele was being spotted out and about with Rob Kardashian by paparazzi. She took to her social media accounts to post a video of Rob Kardashian surrounded by heart emojis. It seems like she is really interested in him and wants to make things work. Especially since she posted a message saying, “Ready to be a good woman to one man for the rest of my life.“ Hopefully, she brings him nothing but positive energy, love, and light.
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