10 Women Rob Kardashian Dated (And 10 That Kris Jenner Would Never Approve Of)

Rob Kardashian was once upon a time a very hot commodity during his prime and dated some of the most beautiful women! The "Keeping Up With The Kardashians" star was known for both his good looks and sense of humour, which made him quite popular.

Although Kardashian is not super adamant about being in the public eye as of recent, he's definitely been keeping himself busy! Rob not only got his own spin-off 'Rob & Chyna' but is also a father now.

The 32-year-old is now getting back into the swing of things and making more appearances both on social media and at events, including Drake's Halloween party last month. Could Rob be back on the market and looking for love? Let's take a stroll down memory lane with 10 women the reality star has dated, and 10 that we're sure Kris Jenner would refuse.

22 Dated: Adrienne Bailon

During the first few seasons of "Keeping Up With The Kardashians", Rob was the apple of many people's eyes, however, he was dating actress and singer, Adrienne Bailon at the time. The two dated for quite some time and is easily one of our favourites that Rob has dated.

21 Dated: Rihanna

Another name linked to Rob Kardashian is none other than the Fenty queen herself, Rihanna! Although this might be news to you, the two were reported to have spent a lot of time together back in 2012. They were often photographed together attending the same events and parties, however, the fling didn't last too long.

20 Dated: Angela Simmons

Rob Kardashian also dated another reality show alum, Angela Simmons. Simmons starred in the shit show "Growing Up Hip Hop", and is the niece of musical legend, Russel Simmons. Although the two didn't date for long, they sure did make quite a cute couple.

19 Dated: Blac Chyna

Rob Kardashian's most recent relationship was with Blac Chyna, who he also shares daughter Dream Kardashian, with. The two shared quite the journey together and definitely had some heated moments. Due to personal reasons, the couple split last year, and have gone on to co-parent.

18 Dated: Naza Jafarian

Before Rob Kardashian completely fell off the face of the Earth, he dated British singer Naza Jafarian. The two were quite comfy in their relationship, so much that Naza even met his family! Despite the two looking good with one another, their relationship fizzled faster than anticipated.

17 Dated: Demi Lovato

Another combo we are sure you didn't expect to have ever dated Rob Kardashian is Demi Lovato. Demi and Rob were spotted quite frequently out in Hollywood and would hang out at the same parties and events. They were photographed a lot back in 2010 when Lovato's career was just taking off.

16 Dated: Karrueche Tran

Karrueche Tran is most popularly known for her relationship with singer Chris Brown, however, she has also been tied to Rob Kardashian. Tran, who is also very good friends with Rob's younger sister, Kylie Jenner, was spotted out with Rob in Los Angeles back in 2015, however, the two claimed they were "just friends".

15 Dated: Mehgan James

Rob Kardashian definitely likes his women having been on reality television, or so it seems that way. Another name thrown into the mix of women having dated Rob is Mehgan James, who is most known for her role in 'Bad Girls Club'. The two dated back in 2017 but broke things off soon after.

14 Dated: Rita Ora

Rob Kardashian and Rita Ora's relationship made national headlines when the two decided to split up back in 2012. As it turns out, Ora cheated on Kardashian ending things off on quite a bad note. The two were never seen together after their break up and rightfully so!

13 Dated: Stassie Karanikalaou


Last up on the list of women linked to Rob Kardashian is new family friend, Stassie Karanikalaou. Stassi, who is currently BFF's with Kylie Jenner, was spotted getting cozy with Rob at Drake's Halloween party. Rob escorted Stassi back to her car where they were photographed looking quite close!

11 No Chance: Chloe Grace Moretz

Chloe Grace Moretz has found herself in the hot seat numerous times with the Kardashians, especially with Khloe Kardashian. Moretz has expressed how she disagrees with the Kardashian's behaviour and how they can influence so many young girls. Khloe was quick to clap back, cutting all ties with the family, including Rob Kardashian.

10 No Chance: Naomi Campbell

Naomi Campbell is one heck of a gorgeous woman, however, we don't think she and Rob could ever be a thing. Campbell has had a few negative things to say about the Kardashians, particularly when Kim and Kanye landed the cover of 'Vogue'. This didn't sit well with Naomi, and she made sure people knew how she felt.

9 No Chance: Blac Chyna

Despite Blac Chyna having dated and sharing a child with Rob Kardashian, it is without saying that Kris Jenner would not want her son to undergo the scrutiny and hardship a second time around. The two split for very good reasons, and we're sure Rob would also want to avoid Chyna at all costs.

8 No Chance: Amber Rose

LOS ANGELES, CALIFORNIA - DECEMBER 05: Amber Rose attends the National Film and Television Awards Ceremony at Globe Theatre on December 05, 2018 in Los Angeles, California. (Photo by Phillip Faraone/Getty Images)


Amber Rose is notorious for feuding with the Kardashians. The model dated Kanye West back in 2010 but broke things off when Kim came into the picture. The two have since made up, but it is without a doubt that Kris Jenner would not let Rob date Amber Rose.

6 No Chance: Pink

As much as we love Pink, she too finds herself on the list of women Kris Jenner would not approve of. The singer took to Instagram to share her thoughts on the family's notorious nude selfies. Pink expressed how women should not be subjected just their bodies, which didn't go over well with the Kardashians.

5 No Chance: Lindsay Lohan

Lindsay Lohan managed to find herself on this list as well! The actress and Kim Kardashian have a long history, one that would not make her a possible candidate for Rob Kardashian. Although LiLo and Kim haven't crossed paths in years, we're sure she still is not Kris Jenner approved.

4 No Chance: Jordyn Woods

Considering the recent events that occurred earlier this year, it goes without saying that Jordyn Woods is not an option for Rob Kardashian. Kylie Jenner's former best friend was caught kissing Tristan Thompson, who was dating and raising a baby with Khloe Kardashian. Due to the unfortunate events that transpired, we're certain that Kris Jenner would not give Rob the green light for Jordyn.

3 No Chance: Naya Rivera

Naya Rivera is also on the list of women that Kris Jenner would have to say no to! The 'Glee' actress took to her social media platforms to call out Kim Kardashian for posing nude on the cover of Paper Magazine. "You're somebody's mother", the star wrote, causing loads of backlash that Rivera was surprised to receive.

2 No Chance: Jameela Jamil

Jameela Jamil is known for speaking her mind on matters that are close to her heart, and the Kardashians seem to be one of them. Jamil is known for her tweets and opinions regarding the family, and how she believes they are "toxic" to young girls, making her an easy no on Kris Jenner's list.

1 No Chance: Taylor Swift

When it comes to getting Kris Jenner's approval, we are certain that Taylor Swift would get an automatic no. Considering the past the family has with Swift, it goes without saying that she would not fit in with the Kardashians, making her a no-go girlfriend.

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