Being in a loving relationship can be pure bliss, and breaking up can pretty much be the total opposite. Dating is hard enough for the average person, and being part of a super famous celebrity family can only add more pressure to an already stressful situation. Let’s be honest, when any Kardashian starts dating someone new, the whole world wants to know all about it. Having millions of people know every intimate detail about your love life can be a challenge, but being exposed is definitely part of the hefty price of fame when you’re romantically linked to a Kardashian. Of course, the Kardashians are a total hot commodity, and they have provided us with some seriously epic exes over the years to look back on. Though we’re pretty certain they wish we could just forget all about their past failed romantic endeavors, these former flames left a lasting impression that is sure to carry on for years to come. Take a walk down memory lane. Here are 15 of the most unforgettable Kardashian exes ever.
15 Ray J
The title of "most notorious Kardashian ex of all time" definitely goes to Ray J. Though his original claim to fame was being an actor, recording artist, and the younger brother of Brandy Norwood, these days Ray J is best known as Kim Kardashian’s old flame. Ray linked up with the future queen of reality TV back in 2003 and their relationship carried on until 2006. While both stars have had their fair share of significant relationships since then, their names will forever be synonymous with each other for one monumental reason.
In 2007, a very private adult home movie that the couple filmed in the early stages of their relationship was made public when Vivid Entertainment distributed the tape under the title "Kim K Superstar." The movie would ultimately catapult Kim and her family into instant fame. While Kim and Ray J insisted that the video was stolen property and it was filmed for their eyes only, many allege that it was Kris Jenner who orchestrated the entire plan in an effort to make her daughter famous. It’s been almost ten years since Kim and Ray J called it quits, and we’re all still buzzing about them as if it were only yesterday. The former pair’s film went on to rake in millions of dollars and still remains the best-selling celebrity tape of all time. Since then Kim has gone on to become one of the biggest celebrities on the planet. Ray J has dabbled in reality TV and rap music. In 2013, Ray released the controversial track ‘I Hit It First,’ which was an indisputable reference to his past relationship with Kim long before she made it big. What can we say - Kim and Ray J’s romance is definitely one for the record books. It seems like no matter what he does; Ray J will forever be just a guy who used to date one of the Kardashians.
14 Kris Humphries
Before he met Kim Kardashian, Kris Humphries was best known for his career as a professional basketball player. Six years later, we all still remember Humphries as the guy who was married to Kim for a whopping 72 days. The unforgettable duo began dating in October of 2010 and tied the knot on August 20, 2011, in an extravagant televised wedding that totaled $10 million. In true Kardashian fashion, the entire rise and fall of their relationship was documented on their hit reality series, Keeping Up with the Kardashians. Viewers witnessed Kim falling fast for the hunky NBA star, but unlike most people in her life, Kris wasn’t afraid to give Kim a much-needed (though sometimes harsh) reality check whenever she was being overdramatic.
Some say that their entire love affair was just a carefully plotted scheme to keep Kim in the spotlight while giving her a high-profile story line for their TV show, but Kim insisted that they were the real deal. Apparently, Kris didn’t agree with Kim’s claims and he responded to her divorce request by filing for an annulment after alleging that their marriage was fraudulent. Their divorce was finalized on June 3, 2013, and by that point, Kim was already in a relationship with her next husband-to-be. Humphries is still playing in the NBA, but nobody could ever forget his very public past with a Kardashian.
13 Scott Disick
Scott Disick met Kourtney Kardashian in 2006 after being introduced by their mutual friend Joe Francis, the creator of Girls Gone Wild. Longtime fans of Keeping Up with the Kardashians will definitely remember Disick being prominently featured on the show since it’s early seasons, earning him a spot as everyone’s favorite former Kardashian flame. Aside from his snappy one-liners, Scott is simply best known as Kourtney’s unforgettable ex.
The on-again/off-again couple has widely had the best and worst of their rollercoaster relationship captured on camera, making some seriously captivating reality television if you ask us. The couple has broken up a number of times over the years, mostly due to Scott’s hard-partying ways. On the brink of a breakup in 2009, Kourtney discovered she was pregnant with Scott’s baby. Since then, Scott and Kourtney welcomed two more children into the world. Kourtney finally pulled the plug in 2015, but they can't seem to stay away from each for too long, and now they are officially back together. One thing is for sure, Scott has become a fixture for the Kardashian family and millions of fans around the world.
12 Adrienne Bailon
Some of us may remember Adrienne Bailon as the lead singer of the girl-group 3LW, others know her from the time she was one of Disney’s Cheetah Girls, there’s no denying that she’s best known as one of Rob Kardashian’s ex-girlfriends. Adrienne and Rob got together in 2007, just as Keeping Up with the Kardashians was beginning to become the phenom it is today. Naturally, Adrienne made regular appearances on the show during the course of their relationship, as she was the focal point of Rob’s life at the time. They even got matching tattoos of each other's names.
Though Rob seemed to be completely enamored by his lady love, he admitted that he was unfaithful and that was what ultimately ended their relationship in 2009. In 2014, Bailon spoke to Latina magazine about not being able to shake the stigma of dating a Kardashian, saying, “to be stuck with that Kardashian label, that was so hurtful to me and to my career.” Adrienne has since gone on to co-host a daytime talk show called The Real, where Rob is still surprisingly a large topic of conversation. On a recent episode, she was filmed getting her tattoo removed from her derriere once and for all; a clear indicator that she was totally over him and ready to move on once and for all. Whether she’s willing to accept it or not is still to be determined, but Adrienne Bailon will always be one truly unforgettable Kardashian ex.
11 Rita Ora
If we know anything about Rob Kardashian, it’s that he’s never been one to have a super stable romantic relationship. The reality star briefly romanced British singer and actress Rita Ora in 2011, but as with most of Rob’s relationships, their love just wasn’t built to last. Rob publicly accused Rita of trying to keep their love affair a secret because she thought going public would be damaging to her budding career. Nobody even really knew that they were an item until after they parted ways and once Rob went on a Twitter tirade against his unnamed ex.
Rob went on to say, “She cheated on me with nearly 20 dudes while we were together. 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?!” Ora was also a topic of discussion on episodes of KUWTK, with Rob blaming a portion of his depression on his failed relationship with the starlet. Of course, Rita Ora has advanced in her music career and gone on to date other celebs (such as Calvin Harris), but she will always be a totally memorable Kardashian ex to us.
10 Lamar Odom
Long before he linked up with Khloe Kardashian, Lamar Odom was already a celebrity in his own right. The professional basketball player met Khloe at a party in 2009 and they instantly hit it off. Khloe and Lamar’s love was so strong that they didn’t waste any time making things official, and the two shocked their friends, family, and fans when they announced their engagement just days into their relationship. The couple wed exactly one month from the day they met, and although their rushed romance seemed unorthodox at first, the bond between Khloe and Lamar was undeniable.
Everything seemed great for the lovebirds over the next couple of years, and they even went on to star in their own reality series, titled Khloe & Lamar. But things were becoming increasingly stressful behind the scenes. It hadn’t become public knowledge yet, but Lamar was battling some very serious addictions, and his bad-boy ways were taking a heavy toll on the marriage. Once news of Lamar’s personal demons came to light, Khloe filed for divorce in 2013. The duo would briefly reconnect over the course of their separation, but all hope to rekindle their romance would be lost when Lamar would slip back into his old habits. The couple’s divorce was officially finalized in October of 2016 and Lamar solidified his spot as Khloe’s ex once and for all. Though he once had an incredible career in the NBA, his time on the court is likely to be forever overshadowed by his highly publicized romance with a Kardashian.
9 French Montana
Once Khloe finally began to embrace the perks of being single, she didn’t waste any time moving on to her next fleeting love interest. French Montana stepped into Kardashian territory in 2014, following Khloe’s initial split from her ex-husband. The duo only dated for a couple of months before ending their romance, but that was just enough time to solidify the rapper’s position as an unforgettable Kardashian ex. French Montana appeared on a number of episodes of Keeping Up with the Kardashians and Kourtney & Khloe Take The Hamptons, though many viewers felt that he was just with Khloe to boost his own image.
Few people may have heard of French Montana in his pre-Kardashian days, but thanks to Khloe he’s become a household name. Although their relationship fizzled out in December of 2014, French and Khloe have remained very amicable exes. French recently told People magazine “We're gonna be friends forever, me and Khloé. We got a special kind of relationship. That's one of my best friends." French also maintains a strong bond with fellow Kardashian flame, Scott Disick, as well Kylie Jenner’s longtime BF, Tyga. We’re glad that even though things didn’t exactly work out for this couple they can still remain on good terms, but it’s super likely that French Montana will forever be associated with his ex. After all, we wouldn’t be talking about him he didn’t date a Kardashian, now would we?
8 James Harden
The women of the Kardashian clan surely can’t seem to resist a professional athlete, can they? NBA star James Harden quietly began romancing Khloe Kardashian in the summer of 2015. The adorable couple appeared to be the real deal, even though the relationship was only in its early stages. While their partnership initially seemed promising, the pair was definitely faced with some tough obstacles. At the time, Khloe’s divorce from Lamar had still not been finalized, but that wasn’t a problem for Harden. Odom was hospitalized following a near-death experience, and Khloe immediately rushed to her husband’s side.
From a legal standpoint, Khloe was still technically Lamar’s wife, and she became responsible for some very serious decisions regarding his health. Harden stuck by his girlfriend even though she was at her ex’s bedside, showing that he was loyal to his relationship and understood the difficult situation Khloe was in. While Khloe refuted claims that she was leaving James to get back with Lamar, the couple ultimately did split in February of 2016 likely due to stressful circumstances that took place outside of the relationship. James Harden is still known for his skills on the court, but there’s no telling if he will be able to shake the title of being Khloe’s ex anytime soon.
7 Reggie Bush
Let’s be honest, who could forget when running back for the Saint Louis Saints Reggie Bush and Kim were an item? They made one super attractive power-couple that gave all of us some serious #goals. Reggie and Kim first got together in 2007 after meeting at the ESPY awards. Though Kim wasn’t the mega-celebrity she is today, Reggie made multiple appearances on Keeping Up with the Kardashians and was well aware of his girlfriend’s goals of superstardom. The pair was crazy about each other, and watching their love story unfold on TV was everyone’s guilty pleasure. Though they seemed like a perfect match at the time, things just didn’t pan out for these two. They briefly parted ways in July of 2009 only to reunite in September of that year.
The couple trudged along for another couple of months before ultimately calling it quits for good in 2010. Of course, the breakup chronicled on reality TV, and Kim appeared to be crushed by the demise of her romance with Reggie. The pro-athlete wanted to focus all of his attention on his football career and didn’t enjoy being in the spotlight quite as much as Kim did, which caused a few rifts in their relationship and undoubtedly played a part in their split. While Reggie continues to have a very fruitful career in the NFL, there is no way anyone will ever forget he used to be Kim Kardashian’s arm candy.
6 The Game
When it comes to their love lives, the Kardashians certainly have a type (rappers and athletes) and the dating pool certainly gets a whole lot smaller when sisters are attracted to the same kind of guys. Rap star ‘The Game’ has been hanging out with the Kardashians for a number of years now, dating way back to 2006 when he and Kim were briefly involved in a romantic relationship. It’s pretty much common knowledge that Kim has a history with The Game, but the rumor mill began buzzing when Khloe was pictured out with the rapper on multiple occasions in 2014. The duo has long been friends, but there’s little denying that they were an item for a brief moment in time once a video surfaced of Khloe twerking at the club alongside the recording artist.
Both Kim and Khloe have moved on from their short-lived flings with The Game, and though he is known for more than his trysts with the famous sisters, he is making his mark as one seriously unforgettable ex. Recently, the star was featured on a song called “Sauce,” where he boldly claims to have bedded three Kardashians. Naturally, The Game’s claims made headlines, and people began actively trying to figure out just who the alleged third Kardashian was that he had been with. Game recently appeared on an episode of The Wendy Williams Show to set the record straight... In a huge plot twist that no one saw coming, the rapper confirmed that the third girl in question was actually Blac Chyna, who is currently engaged to Rob Kardashian. Well, there you have it. The Game is truly an unforgettable Kardashian ex in every sense of the word. Needless to say, after striking three times with this famous family, it’s super safe to assume that he won’t conquer a fourth family member any time soon.
5 Rashad McCants
We all know that Khloe Kardashian’s love for basketball players runs deep and perhaps it all started when she briefly dated NBA player Rashad McCants in 2008. As far as we know, McCants was the first pro-ball player to win Khloe’s heart, and portions of their short-lived relationship were filmed for early seasons of KUWTK. Though McCants never actually appeared on an episode of the reality show, Khloe often spoke of him and was recorded having phone conversations with him on a few episodes.
Rashad played for the Minnesota Timberwolves at the time, a circumstance that made their relationship long distance since Khloe resided in California. Khloe was obviously smitten with the budding ball player, but many viewers will never forget the infamous moment where Khloe and Kim hacked into his voicemail and discovered proof of his infidelity. Khloe was fuming at Rashad’s cheating ways, and she pretty much ended the relationship on the spot. McCants has publicly accused Khloe of scripting the entire scene for the sake of reality TV, but Khloe painted an entirely different picture of their untimely breakup, calling him a “loser” in an interview with OK magazine in 2009. Rashad really hasn’t done much career-wise since he had his fifteen minutes of fame dating Khloe. It’s pretty clear that Rashad McCants’ main claim to fame is that he formerly dated a Kardashian.
4 Todd Waterman
Avid fans of Keeping Up with the Kardashians will have no trouble remembering the name Todd Waterman, the scandalous former flame of Kardashian family matriarch, Kris Jenner. In a 2012 episode of the reality series, Kris casually agrees to meet up with her ex-lover in a bid to see if the two still shared a spark. Of course, this was an outrageous action given the fact that Waterman was one of the reasons behind Kris’s divorce from Robert Kardashian many years ago, as the two were carrying on a secret affair. At the time of their reunion, Kris was still in her second marriage, and seeing Todd was a huge sign of betrayal to everyone in her family.
That same year, Waterman released shocking private details about his former relationship with Kris that was credited with destroying her first marriage. Their tryst began in 1989, more than ten years after Kris married Robert. Waterman insisted that their feelings took over the guilt of infidelity, saying “The love swept us away. We made our own different reality. It was special, it was a little crazy, a little wild. We didn’t exercise caution or self-restraint. I think we were both very much in love.” Kardashian eventually unearthed the details of his wife’s affair after hiring a private detective, and we can only imagine what happened after that. Kris’s relationship with Todd proved to be a shocking one, but Waterman will forever go down in history as one of the most contentious and unforgettable exes of all.
3 TJ Jackson
We all know that Kim K has had a long list of famous ex-lovers over the years, and it all started way back in 1995 with her first love, TJ Jackson. Of course, TJ’s uncle was none other than legendary pop icon Michael Jackson, and his father is Tito Jackson of ‘The Jackson Five’ fame. Kim and TJ began dating in their teens, with Kim openly stating that Jackson was her first romantic experience ever. The couple had been through a lot together as most young couples do, including going to prom and having their families develop a close bond. Kim even said that she spent her fourteenth birthday at Michael’s infamous Neverland Ranch alongside her BF.
The high school sweethearts had a good run, but their romance eventually fizzled out by 1999 and the couple called it quits. Last year, Jackson spoke to the media about his past relationship with the world’s most famous reality mogul, saying "I still talk to the family every now and then, though not too much because our schedules are pretty busy." Although TJ’s family name is incredibly famous in its own right, there is little denying that he will forever be linked to Kim and the Kardashian brood in a big way.
2 Jaden Smith
Though it might seem like Kylie Jenner and Tyga have been together for what feels like forever, there was someone else who won her heart long before her current beau ever came into the picture. Kylie’s first real high-profile romance was with Jaden Smith, and though he is easily recognizable as the son of Will Smith and Jada Pinkett, he is also known for being one super unforgettable Kardashian ex.
While the two young stars were friends for many years before deciding to date, but their romance only lasted a mere eight months in 2013…though that is considered to be a serious commitment when you’re not even old enough to drive. Kylie and Jaden kept us all guessing about whether or not they were actually an item, but paparazzi photos and Instagram pictures of the duo holding hands certainly proved that they were the real deal. Even though their romance ended years ago, Kylie and Jaden remain good friends and hangout on a regular basis. We imagine that might be a bit awkward for Tyga, but then again his ex is also involved with Kylie’s brother, Rob.
1 Blac Chyna
Let’s face it: whether the rest of the family wants to admit it or not, Blac Chyna has become a pretty great thing that has happened to Rob Kardashian. After years of living in seclusion from the spotlight that the rest of the Kardashians crave, Rob finally reemerged back onto social media and reality television in a big way. Rob had a reason to be happy and he wanted the world to know it, and he had none other than Blac Chyna to thank for his new outlook on life. Though Chyna has been a longtime friend of Rob and his sister Kim, the electrifying duo didn’t become an item until earlier this year. The two began dating in January of 2016 and come three months later they were already engaged. Along with their engagement came the surprise announcement that Chyna was pregnant with Rob’s baby.
What can we say, this couple definitely moves at lightening speed! They welcomed their daughter, Dream Renee in November and they all lived happily ever after…or so we thought. Chyna and Robs’ relationship has been a rocky one, as the pair tends to make up and break up on a weekly basis. Since their engagement announcement, the pair has been entangled in public spats on numerous occasions, with Rob going so far as to delete all photos of Chyna from his social media accounts only weeks before she was supposed to give birth. Fortunately for the general public, these two lovebirds scored a reality show of their own, called Rob & Chyna, where viewers got to see their volatile fights first hand. Throughout the course of the season, Chyna accuses her man of texting other women and Rob moved out of their shared home on a number of occasions. We never know whether or not Chyna and Rob are together or apart, but if history repeats itself, there’s a pretty strong chance that Blac Chyna will become the absolute most unforgettable Kardashian ex there ever was.
Sources: MTV.com, USMagazine.com, OKMagazine.com, DailyMail.com
