Dating and relationships can be the greatest challenge some of us will face. There are songs about it, shows, and movies that all revolve around finding that one person and falling in love. Just because you let your heart get connected to someone doesn’t mean that you’ll be with them forever, and even more challenging than dating is breaking up, which can sometimes wreck people’s lives. We all have that one crazy ex that seemed like they never fully recovered from the separation. Maybe you’re even the crazy ex! Either way, it can be certainly hard for some people to let go.
Imagine the relationships that celebrities go through! Getting broken up with by someone and then having to watch them grow and prosper can be challenging. Even though we might have loved a person at one point, the desire to see an ex worse off when you’re not in their life anymore can be greater than that original attraction. When it comes to the exes of the Kardashians, having to watch them grow into one of the wealthiest families in Hollywood has to be rather challenging. On one hand, we don’t blame them for their inability to leave behind their ex. On the other hand, they’re just another person that got dumped and can’t seem to move on.
Some people might not ever be able to let their feelings go, and others might have never really had them in the first place. Either way, here are with 15 Kardashian-Jenner exes that can't seem to get over the sisters.
15 French Montana Owes His Fame To Khloe
French Montana wasn’t very well known before he started popping up on Keeping Up with The Kardashians. He ended up making a few appearances while he dated Khloe after she divorced from husband Tristan Thompson. Many people believe that if he hadn’t dated Khloe, he might not have the status and fame he does now. The pair has remained friends, but when it comes to their status now, some wonder if he’s still got feelings for Khloe. When asked what he thought about her pregnancy, he stated,
“Let me tell you something, man. I just want everybody to be happy, man. That’s all we’re promoting. So, when there’s negativity, I duck and move, papi. We’re doing good, we’re living good. We’re healthy, we’re wealthy.”
Photographs of Khloe’s certain love, Tristan Thompson, popped up on the Internet showing him being a terrible boyfriend. Despite the cheating rumors, Khloe still let him in the delivery room, a source stating, “we're told Khloe's putting her feelings on hold, realizing for better or worse Tristan is the father of their child and knowing a bond between father and child can be cemented in the delivery room.”
After the rumors broke the Internet, French Montana was caught following Khloe on Instagram, The Shade Room posting a screenshot with the caption, “When your ex finds out how your new thing's been treating you.”
14 James Harden Said Dating Khloe Was The Worst Year Of His Life
There’s an alleged Kardashian curse for athletes who decide to date one of the members of the beauty-obsessed family. The idea is that after breaking up with a Kardashian, or even by dating them in the first place, the boyfriend’s life and career go downhill. James Harden has seemingly survived, but he also stated that dating Khloe Kardashian was the worst year of his life. That’s a pretty bold statement, but it mostly had to do with the attention that dating such a high-profile celeb brought, stating,
“I didn’t like all the attention. I feel like it was for no reason. I wasn’t getting anything out of it except my name out there and my face out there, and I don’t need that. I wasn’t uncomfortable, but it wasn’t me.
I don’t need pictures of myself when I’m driving my car. Who cares? What shoes am I wearing? Who cares? Where am I eating? Who cares? It was unnecessary stuff that I think trickled down to my teammates. I had to eliminate that.” Their relationship ended as the long-distance became too much for Khloe. She also claimed that he was betraying her during their time together as well.
13 Harry Styles Revealed He Wrote Some Songs About Kendall
Harry Styles and Kendall Jenner were linked together at one point, a romance that they kept pretty well hidden. It seems after they broke things off they were more likely to discuss their relationship. Harry Styles even admitted that some of the songs he wrote were about Kendall. When asked about his album and writing songs based on the model, Harry said,
“Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap and hope they know it's just for them.”
After they broke up, they were spotted a few times together, a source saying Harry wanted to work things out and get back together. The source said, “Harry has thought all along that Kendall is hot and was sort of just waiting for a chance to spend more time with her again." Kendall had no interest in getting back with the One Direction singer, a source saying she had no interest in hanging when they ran into each other at a party. They said, “Kendall is over Harry’s bull and she totally took the high ground — she just smiled at him then politely ignored him for the rest of the night. She had no idea he was going to be there, but she really didn’t care. Kendall knew she was going to run into him at some point, so in a way, she’s glad it’s over and out of the way.”
12 Tyga Still Has Kylie's Name On his arm
Kylie Jenner and musical artist Tyga were known for dating on and off for a few years, eventually ending things for good. Kylie and Tyga had tattoos dedicated to each other at one point, but when Kylie officially ended things, she got hers covered up. She just had a small “T” at one point, eventually altering it to “LA.”
When asked about his breakup and relationship with Kylie after the split, Tyga stated, “You just get older, you get me? It was a relationship in front of the world, and that was it. She has her new life, I have my new life, and that’s it. There’s no bad blood, no problems.”
Kylie said the breakup was good and that there were no hard feelings. She said on her short show, Life of Kylie, “There was absolutely not one thing wrong with me and T. He and I will always, always have a bond. There was no crazy fight, we just decided, well, I decided, that I’m really young. I don’t want to look back in five years from now and feel like he took something from me when he’s really not that type of person.” They might be with other people now, but Tyga hasn’t been reported to have removed his tattoo yet, potentially still holding onto his last girl.
11 The Game didn't want to disrespect Kanye
The Game is another musical artist that was linked to the Kardashians. In one of his songs, he claims he was with three of them. He never outright said who he was with, though it was clear one of them was likely Khloe Kardashian. Wendy Williams pressed him to spill the details on who the others were, and when she asked if Kim was among the three, The Game just stated, “You know what? I’ll tell you this, Kanye is a really good friend of mine and they got really, really beautiful kids and I don’t want to disrespect their family."
Wendy listed the rest of the Kardashians, making everyone wonder if Kourtney was the third, but he said they were never together. Kylie and Kendall aren’t technically Kardashians, so that had many wondering if he was referring to Rob. It turns out, he was actually referencing Blac Chyna, since when she was engaged to Rob, she was predicted to become Angela Kardashian. The Kardashians denied it, but he stands by his word. It’s never a good look for someone to brag about something like this.
10 Reggie Bush Didn't Handle His Break Up With Kim Well
Before becoming Kim Kardashian West, she was known for dating athletes, mostly. She had one boyfriend, Reggie Bush, that she was very open with discussing their relationship on an early season of Keeping Up with The Kardashians. She ended up ending things with him, but like many of her exes, it wasn’t exactly easy. He would often call her after the breakup, even having a confrontation with her over the phone on an episode of the show. It was clear he didn’t handle it well, but seeing as how their lives went in such separate directions, it makes sense it wasn’t exactly easy for him to let go.
Recently, online fans freaked out after Reggie Bush shared photographs of his family. Many people noticed the similarities between his current wife and Kim Kardashian. It even looks like their little daughters could be siblings! There’s no denying that North West is Kanye’s daughter, but the similarities are certainly eerie. Many girls look like Kim Kardashian now, using her beauty tips and copying her style, but it’s still strange to see just how close the two resemble one another.
9 Jaden Smith couldn't let Kylie go
Before Kylie was pushing her baby around in a $16,000 stroller, she was caught making out with Will Smith’s son, Jaden Smith, after leaving the movies when she was just a teen. It seemed like it was just young love, but some wondered if Jaden Smith might still have feelings for Kylie after rumors surfaced that he was the reason her and Tyga split in the first place. A source close to the couple stated, “Kylie and Jaden have been hanging out lately and it made Tyga suspicious. He thought something might be going on. So that was one issue.”
Kylie has had plenty of guy friends, and Tyga has been known to have plenty of lady friends surrounding him as well. The source continued by stating that these were likely just rumors, and that “she has a close relationship with Jaden since they were very young but nothing romantic has happened with them since she has been with Tyga. Jaden, though, will always love Kylie and Kylie will always have a love for Jaden. They grew up together and were each others' first loves.”
8 Scott Will Always Be Obsessed With Kourtney
Scott Disick and Kourtney Kardashian have had a pretty messy relationship, and a lot of it was chronicled on Keeping Up with The Kardashians. Even though Kourtney officially ended things and moved onto a younger model, she stated on the show that Scott still called her, telling her sister Khloe a lot of what he had to say. Kourtney said, “Last night, Scott called me at like 2 in the morning — he never calls me late at night, ever. And he was just ranting, like, ‘What are we doing in life? What are you doing? What am I doing?’ And I’ll go, ‘But what are you doing?’ But then he’ll say, ‘But what are you doing? Is it any better?’
By the end of the conversation, I just was like, ‘I have a boyfriend. He’s 24 years old. It’s not the craziest thing that’s ever happened in the world!’ And he was like, ‘He’s your boyfriend?’ And then he hung up the phone.”
A source elaborated on the story, stating, “Kourtney and Scott’s relationship is a bit more complicated right now. They’re not at the best place and Scott isn’t a fan of her boyfriend. He really wanted to get back together with Kourtney at one point and was very serious about it, but they never reconciled, so there are still hurt feelings there.”
7 Blac Chyna Doesn't Get Paid As Much For Gigs Now
At one point, Blac Chyna was on track to become a Kardashian herself, engaged to Rob Kardashian and pregnant with their daughter dream. She was becoming a member of America’s royal family, and with that status, she was also going to be able to earn a ton of extra money to cash in on her new last name. The couple ended up going their separate ways, and with that split also came a lower club appearance fee. TMZ reported Chyna doesn’t get paid nearly as much for club appearances and other events as she did when she was with Rob. The gossip site stated,
“The numbers are staggering. Blac Chyna went from booking gigs that paid her up to $30,000 not too long ago in her heyday with Rob and Co. to now struggling to snag more than $7,000 per gig. That's what several top club promoters in Cali told us, and it gets worse.
One promoter said he wouldn't pay her a penny more than $5,000 because Chyna without Rob is like Sonny without Cher.”
6 Adrienne Bailon Had To Get A Rob Tattoo Removed
Adrienne Bailon was first known for being one of The Cheetah Girls. After her Disney stardom, she ended up appearing on Keeping Up with The Kardashians when she was dating Rob. The couple broke up, but Adrienne still talks about the relationship often on her current talk show. She told audiences,
“When I broke up with Rob Kardashian, my breakup buddy was his sister Kourtney who at the time had broken up with Scott for a moment. She was so much fun,
I was definitely more the sad one, crying at home and she was like, ‘No girl, we are going to go out. We’re going to hit the clubs in Hollywood. We’re going to have so much fun!’” Some wonder if her talking about him so much on the show is a sign that she might still have feelings for Rob. She also told a story of how they still share a responsibility that some still take very seriously. She stated, “Me and, actually, Rob, are godparents to my little cousin. I think, once we broke up, we never even thought about it again. I don't think my family was seeking him out, like, 'You're a bad godfather. You didn't come back.' Things happen. People move on. It just gets weird. We were together. We went to North Carolina for her christening. It was a great moment, but I think even now, they'd be like, 'Nah,' because it's weird!"
5 Lamar got kicked out of court after insulting Khloe
Lamar Odom and Khloe Kardashian’s relationship was one of the most well-known Kardashian relationships since they even had their own show. After dealing with so many problems, the two called it quits, but Lamar wasn’t willing to go down without a fight. He allegedly got kicked out of court after telling the judge that Khloe’s smelled like "earring backs!" He likely just stated such a harsh comment to help get back at Khloe. He might want to hurt her, but that doesn’t mean he’s over her. He’s publicly stated,
“I want my wife back. Khloe is important to me. She's been through all of this with me and she stood right by my side so I just want to repay her.”
And when it comes to her family, he stated, “I just want to tell them I'm sorry for all that wasted time and wasted energy [...] I didn't know who I was, so I couldn't take care of myself. I damn sure couldn't take care of anybody else." Once rumors of Tristan’s betrayal surfaced, a source close to Lamar also stated, “Lamar is very concerned to read the reports [...] and he would absolutely get back together with Khloe.”
4 Ray J Mentioned Kim In A Song
If it weren’t for Kim Kardashian and the release of the tape she made with artist Ray J, the entire family might not have been the insanely popular and successful stars they are today. At the same time, Ray J was also in the tape, but he doesn’t have a makeup line that’s projected to make millions or other successful business adventures that Kim Kardashian has been able to excel in.
Instead, Ray J decides to dis the family in a few different tracks, such as “I Hit it First,” and “Famous.” One of his lyrics states, "She might move onto rappers, and ball players, but we all know I hit it first" and “[...] but now baby chose to go West”
He wasn’t last to have the final word when Kanye West ended up dissing him in one of his tracks as well. Ray J wasn’t totally cool with that, however, and stated, “don’t put me part of nothing that’s weird, that don’t make sense. I’m engaged. My marriage is all messed up because of craziness. I’m not part of nothing crazy. I walk down a good path. My fiancée is tripping. It’s all bad in my world, and that ain’t cool.”
3 Kris Humphries Made the Divorce Difficult
Kim Kardashian was married to Kris Humphries for a brief time, ending it before it even got a chance to start. She shared the difficulties of the separation on her show, stating, “My divorce has been really draining, really stressful. I just want to leave this chapter of my life behind me. I think someone just wants to make it so difficult. When one person just wants a divorce and the other one is just pissed, they try to make it so difficult." When asked about Kim now, a source close to Kris Humphries says,
“Kris can’t believe Kim has stayed married to Kanye for four years now. He knows how challenging it is to be in the Kardashian family, so he is shocked and surprised that Kanye has been able to tolerate all the challenges of being in the notorious spotlight.
Kris is also shocked that Kim has not changed her mind about Kanye or tried to leave him for someone else. Kris has never been happier with his own life since severing ties with Kim and he laughed when he heard that she was having another anniversary with Kanye. He no longer has any resentment toward Kim, but he is glad it’s not him that is still a Kardashian.”
2 Caitlyn Jenner and Kris aren't on the best terms
Caitlyn Jenner and Kris Jenner have had a complicated history, and though they’re not together anymore, it seems Caitlyn has had a bit more trouble getting over Kris than the other way around. Caitlyn wrote a tell-all book painting Kris Jenner in a pretty harsh light. Of course, Kris denies much about what was said about her in the book, but that doesn’t make the truth any clearer. Kim stated,
“She’s so angry at mom, like for no reason. She said, ‘I didn’t see a dime of my money.’ She was insinuating that mom took the check and pocketed it and had this huge savings.”
Kim also said, “I feel like she’s been through so much and is promoting this book and she’s saying all these things. I don’t think it’s necessary and I just feel like it’s unfair, things aren’t truthful. Kendall and Kylie, that’s their dad and I think my mom’s been so respectful for so long and always wanting Caitlyn around and always wanting to have a great relationship with Caitlyn. I feel like it’s taken her a really long time to be honest with herself, so I don’t expect her to be honest about my mom now. But it’s just so hurtful. I wish her all the success in the world, but not at our expense.”
1 The Guy who couldn't get over Kris
Before Kris was married to Caitlyn Jenner, she was Robert Kardashian’s wife. The two ended their relationship and one of the reasons was Todd Waterman. He was much younger than Kris, too. The relationship was messy. Kris ended up having a “run-in” with Todd on an early season of Keeping Up With The Kardashians, even though many people have stated that it was likely staged.
There were rumors that Todd and Kris might have tried to rekindle things, with him saying, “Maybe she was hitting a doldrum in her marriage because I got the impression that she was open to getting together and then I came back to LA and we would talk on the phone and make the appointment, and say ‘Starbucks today’ or something, but she could never get herself to do it. She never followed through and it’s probably best we didn’t really.” Kris has since moved on, and Todd isn’t allowed to say much without risking getting in serious legal trouble.
References: Reality Tea, TMZ, People, US Magazine, E Online