Although Rob Kardashian likes keeping his low profile life, his romantic life is not much of a secret.
Rob Kardashian has been linked to several females here and there. Some you might recognize as they are in the entertainment industry and others are just randoms, but obviously wanted something out of it when they allegedly hooked up with Rob. That’s not totally accurate but that’s usually how it goes.
If the 28-year-old is not dating a high profile singer or actress, he’s dating someone we eventually find out through social media or just reports. Rob has been really abnormal with everything in his life, including his love life. Of course, there is no way Rob would even comment on who he is dating but we can try putting the pieces together based on all his actions. The only problem is the former reality TV star has a really distinct way of doing things online so it doesn’t really help us confirm any romance rumors. He’ll post a random photo of a girl on Instagram along with an interesting caption then he’ll take it down, just like he does with the rest of his posts. Just a few days later, Rob posts another photo of a random girl or sometimes a celebrity and rumors start spreading outrageously. The point is, Rob drives us crazy about who he’s dating at the moment and we can’t get enough of it.
The following captures a list of girls, all of which have somehow been romantically linked to the Keeping Up With The Kardashians star.
13. Kara Monaco
Rob Kardashian was rumored to have dated American model, Kara Monaco, in 2008. The model served as Playboy’s Playmate of the Year in 2006. They first met on a blind date and then hit it off and started dating. According to HealthyCeleb.com, the two were linked to each other before he got serious with singer and actress, Adrienne Bailon. Apparently, the reality TV star cheated on Kara with Bailon and eventually left the model for the R&B singer. We can say Rob wasn’t that into her after cheating on her with someone he later seriously fell for.
12. Lisa Ann
Rumor has it that Rob and adult film star, Lisa Ann, hooked up in 2009. You can possibly imagine the outrage everyone had when they heard about the squeaky clean Kardashian getting down and dirty with this adult actress. She has starred in the flick, Who’s Nailin’ Palin? According to the adult film star herself, Rob had hit on her while he was at the gym which was around the time his sister, Khloe Kardashian, was getting ready to marry now estranged husband, Lamar Odom. TMZ got to talk to Ann where she gave the deets on their steamy fling. “Rob treats me like his little teacher and we have a fun sexual relationship that is simple and carefree,” she said. “He brings out the total cougar in me and I just like to teach him things.” Sources say the two ended their fling after just one month of dating.
11. Rosa Acosta
In 2011, the Kardashian was romantically linked to friend and dancer, Rosa Acosta. The two were seen as friends with benefits and Rosa didn’t hold back about the relationship they were having when she spoke with Star Magazine. “We’ve always been friends and flirty,” Rosa told the publication.
The dancer explained she took a few pregnancy tests after the two had sex for the first time. “I took a few pregnancy tests and they came out positive. I went to the doctor who said the baby didn’t attach. Essentially, I had a miscarriage.”
Rosa said Rob was very hands-on with the situation even if he wasn’t prepared for fatherhood. “I’m glad he was there for me as a friend and ready to step up as a dad.”
10. Dollicia Bryan
Another rumored fling Rob was having was with Dollicia Bryan, a woman who was also rumored to have hooked up with Kim Kardashian’s ex-boyfriend, Reggie Bush. When these rumors came out, sources were saying that it angered Kim and a small feud was happening for a minute. The rumors were out of control and Dollicia went on to speak up about the whole situation and didn’t mind expressing her true feelings. “We’re two different women,” she told King magazine, comparing herself to Rob’s older sister. “I’m a mother, so I can never be famous for leaking a sex tape. There’s a huge difference between us. I’ll stay the Queen of talent and acting, but as far as being the Queen of who I’m dating and being in the media all the time; she can stay the Queen of that.” Whoa, things were just not okay between the two. Good thing that it was just a rumor and regardless if true or not, Rob is no longer acquainted with Bryan.
9. Angela Simmons
You might know her as Rev. Run’s daughter on their reality TV show, Run’s House. Angela Simmons is an actress, performer, and TV host. The reality TV personality was linked to the Kardashian in 2010 but to this day, it was just a rumor. News of the two dating broke when photographs came out of them hanging out. This was soon after he broke things off with long-term girlfriend, Adrienne Bailon, and Simmons was called a rebound for the Kardashian. However, Rob quickly took to his Twitter page to deny those rumors of the two hooking up. Nothing ever happened between them after those rumors.
8. Jasmine Sanders
Jasmine Sanders is a model who was once romantically linked to rapper, Chris Brown. When the two broke things off, photos of Sanders and Rob started surfacing online and quickly started rumors of a possible relationship. While hanging out with sister, Khloe Kardashian, and her ex-husband, Lamar Odom, at Encore’s Beach Club in Las Vegas, Rob was spotted getting intimate with the model, poolside. This was just a few weeks after the rumors of him and Angela Simmons came out. On the other side, Chris Brown was seen posting on Twitter, making subtle hints at his ex which made us think he was obviously bothered by the sightings of Rob and Jasmine. Not to worry Chris, their romance lasted only for a minute.
7. Demi Lovato
Yes, this is probably the biggest shocker on this list but again, it only lasted as a rumor. Demi Lovato was rumored to have had a thing with Rob Kardashian in 2010. Lovato, who’s known as one of Kim Kardashian’s close, famous bffs, heard about the silly rumors and laughed them off as they were just as ridiculous to her as they are to us. When photos of the two hanging out surfaced, tabloids quickly jumped to the idea that they were dating but Demi made sure to shut them down. “We’re just friends,” she told RaderOnline. “It’s funny how people can get two pictures of you with someone and everyone thinks you’re dating but that’s totally not the case.” It happens in Hollywood, Demi.
6. Malika Haqq
If you are a dedicated fan and keep up with the Kardashians, you know who Malika Haqq is. Malika is one of the family’s closest friends, particularly Khloe Kardashian. On the show, you can watch the episode where Malika and Rob started flirting as friends but there were times where they got too close for comfort and Khloe didn’t really know how to handle the awkward situation of her brother and best friend hooking up. The funny thing is on the episode, Rob and Malika were actually just messing with Khloe but that didn’t stop the rumors from spreading about the two. You can’t blame them. On-screen, the two “friends” do seem to have a thing for each other but the fact that she is a long-time family friend, might make things awkward so perhaps they rather keep it cordial.
Another shocker. Rumors of Rihanna and Rob hooking up started in 2012 when they were spotted hanging out and ending their activities for the day at a nightclub in Los Angeles, getting awfully intimate. “They were sitting closely at the club, whispering in each other’s ears and clearly flirting,” an unknown source said. “Rihanna and Rob have been flirting for a while.” Awkwardly enough, the “Where Have You Been All My Life” singer was so into her night with the Kardashian that she didn’t notice her controversial ex-boyfriend, Chris Brown, also present at the nightclub while sitting in VIP. Thank god nothing happened between the rapper and reality TV star because that would’ve been ugly. This rumored fling happened just a little after Rob’s relation with singer, Rita Ora.
4. Naza Jafarian
Naza Jafarian was first seen as Rob’s new love interest when he posted a photo of her on Instagram. The world went crazy questioning who is this chick? But that didn’t stop Kardashian from embracing his new girl as he continued to post of their relationship, obviously confirming they were together. He even posted cute messages on Twitter such as “Love, it will not betray you, dismay or enslave you, it will set you free :).” Rob was totally in love with this one. The two were dating in 2013, which marked his third serious relationship ever since Ora.
It even seemed like Rob upgraded from Ora with Naza, according to reports. “Kris Jenner and Kim Kardashian like Naza a lot more than Rita Ora, because she’s a lot like them,” the source stld HollywoodLife.com. “They didn’t really like Rita at all.” Ouch. It is never a good feeling knowing your beau’s family doesn’t really dig you that much. The fact that the family did like Naza, and Rob was head over heels for her, makes us wonder what went wrong between the two.
3. Rita Ora
Rita Ora and Rob Kardashian officially dated from 2011 to 2012, but it wasn’t the smoothest relationship. Although their relationship wasn’t always out in the media, their split sort of hinted they didn’t have the healthiest romance. The two parted ways after a few months of dating and Rob didn’t take it so well. The reality TV personality took to Twitter to express his feelings on the whole thing and it all went downhill from there. “She cheated on me with nearly 20 dudes while we were together, I wonder how many she will sleep with now that we’re apart? But I mean 20?!!!” he tweeted. “How can a woman who is so busy trying to start her own career have time to be with so many dudes all while in a relationship?!” Okay, Rob wasn’t shy about putting his ex on blast at all.
Of course, Rita wasn’t going to let the Kardashian get away with it. In response to his Twitter rant, she explained, “No. Nooooo. To tell you the truth I don’t put energy toward things that don’t need light. You don’t need it.” However, the British singer had also told Glamour U.K. in an interview the relationship was never that serious. Ouch. “I’m not going out with Rob. We were close for a while, but it didn’t work because I was never there.” With all the confusion about what exactly happened, it’s a good thing these two parted ways.
2. Karrueche Tran
Karrueche Tran is an actress and another ex of Chris Brown’s (obviously Rob is on a mission to steal all of Chris’s girls). The rumors of these two dating started late in 2015 when the Kardashian just went ahead and posted a screenshot of their conversation on Instagram along with a selfie Karrueche sent Rob. Everyone couldn’t also help but notice the way Rob playfully spelled her name on his phone as “Karroooooooooochieeeeeee.” However, the brother of the Kardashian klan didn’t hesitate to shut down the rumors of the two having a thing and said that they have been friends since high school. If you do follow Rob, though, on Instagram, you’ll notice he consistently likes Karrueche’s selfies.
With the rumors getting so much attention, Chris was bound to respond, especially when it has to do with his ex-girlfriend who he is known to be very possessive over. A source told HollywoodLife.com that the rapper is not threatened by these rumors, but according to what he is saying, the “Forever” rapper is obviously insecure about the whole situation. “No disrespect to the brother, but Rob couldn’t land Karrueche if he were a pilot,” the unknown source said. “For Kae to leave Chris and try to hook up with Rob would be a serious downgrade. And if there’s one thing Chris knows about Karrueche, it’s that she likes that Hollywood life and Rob can’t give her that. Him posting pictures of Karrueche is like whatever to Chris. He knows nothing sexual will ever happen between the two of them.” Whoever this source is, is obviously a close friend of Chris trying to cover up his jealousy for him.
1. Adrienne Bailon
Cheetah Girl, Adrienne Bailon, is probably the most well-known former girlfriend of Rob Kardashian’s. After all, she was his first serious girlfriend as seen on episodes of Keeping Up With the Kardashians. During the times we watched them together, it was obvious Rob was head over heels for the singer, especially when he got extremely hurt about Adrienne leaving to India for a few months. His sisters were always in support of their relationship so everything was in good hands, it just had its ups and downs experienced by most couples. Unfortunately, the two couldn’t handle the problems any longer and called off their two-year relationship in 2009. However, forward to 2014, drama began surfacing around their former relationship when the The Real co-host made a few comments in the September 2014 Issue of Latina magazine. “To be stuck with that Kardashian label, that was so hurtful to me and to my career,” Adrienne said. “At the time, I didn’t think anyone would even care.”
The Kardashian klan including Rob eventually responded to the comments with Khloe tweeting, “FDB” meaning F*ck Dat B*tch and Rob retweeting it. Kim also stepped in to her brother’s defense and tweeted, “Funny how she says being with a Kardashian hurt her career yet the only reason she has this article is bc she is talking about a Kardashian.” Adrienne didn’t just leave it there but instead apologized and said, “For me, I just didn’t want to be known as anyone’s girlfriend. I wanted to be known for the hard work I’ve been doing since I was 15 years old.” Makes sense. To this day, the two haven’t rekindled any romance or friendship even though it seems a lot of people want it to happen.