Famous Kardashian Exes You Totally Forgot About

Keeping up with the Kardashians is one thing, but keeping up with the men they date might as well be an Olympic sport. The famous family has gripped the nation with their made-for-television antics ever since the late 2000s, when a notorious sex-tape catapulted Kim Kardashian to super-stardom. Her famous momager, Kris Jenner, was able to turn the faux-pas into a serious cash cow, riding the publicity wave as their infamous reality series, “Keeping Up with the Kardashians,” took over E! network for the next 14 years.

Fans of the family know that watching them on television means adapting to their unstable love relationships, which can often rotate as much as the clothes in their closet. From Kourtney Kardashian’s previous on-again-off-again relationship with Scott Disick to Kim’s nearly three-month long marriage to Kris Humphries, there’s a long history of men the Kardashians tend to leave in their wake. Some have publicized breakdowns (Lamar Odom, anyone?) and others run for president (Kanye West didn’t quite make it to the Oval Office).

Several Kardashian exes seemed to fade entirely into oblivion, completely eclipsed by the family’s power (and perhaps some lofty NDAs?). They say all is fair is love and war, but these past lovers may not agree. Here’s a look at several famous Kardashian exes you totally forgot about.

Kim Kardashian went from Paris Hilton’s closet organizer to A-lister, and many speculate that her famous sex tape with ex-boyfriend Ray J was the catalyst. The “Kardashians” star ran into the artist while she was working with his sister, Brandy, in the early 2000s, and they became an item in 2003. While they split up in 2006, their story was just beginning when a sex tape of the two was released by Vivid Entertainment in 2007.

Though Kardashian has denied having any involvement in the release of the intimate video, many have speculated that she and her mother, Kris Jenner, worked directly with Vivid Entertainment and were behind its’ release. Ray J, who seemingly flew under the radar for many years after splitting with the SKIMS founder, went viral in 2022 after he claimed on Instagram Live that his ex-girlfriend and her momager orchestrated the entire sex tape.

“You know what we did! Your mom controlled this whole sex tape deal with Joe Francis and [Vivid CEO] Steve Hirsch — it was her idea to put out the tape with Vivid. All I did was agree,” Ray wrote on social media (via the Daily Mail), also posting a video of what appeared to be a contract between Ray J, Kardashian, and Vivid Entertainment. Kardashian remained quiet over the controversy.

While Ray J may harbor hard feelings about his former beau, he has since moved on to his on-again-off-again wife and “Love & Hip Hop” star, Princess Love, whom he married in 2016 and shares two children with. The pair have since announced plans to divorce four times, with the latest news of their split breaking in 2024.

Before Kourtney Kardashian met Scott Disick, there was Girls Gone Wild founder Joe Francis. The two met in 2004, and according to Francis, she was the other woman. The producer admitted on the “Juicy Scoop” podcast (via Page Six), that he started having a sexual relationship with the Poosh founder while on a trip to Mexico, when he was dating Rod Stewart’s daughter, Kim Stewart, at the time. “Did I have sex with Kourtney on that trip? Yes,” he recounted. “Did I have sex with Kim Stewart on that trip? Yes,” he continued, “and interestingly enough, that is when Kourtney and Scott [Disick] met.”

According to Francis, he was the one to introduce Kardashian to her future baby daddy, who he was close friends with at the time. It wouldn’t be until a year later that Disick and her would start seeing each other, as Kardashian dated the adult entertainment mogul starting in 2005. Their relationship was brief, however, and ended not long after it began. 

Francis eventually fell in love and had twin daughters with model Abbey Wilson, but the two later split and were embroiled in a nasty custody battle. “I would have been better off [with Kourtney] than my situation now,” he expressed on the podcast.

Rob Kardashian’s first girlfriend in the spotlight was former Cheetah Girls singer Adrienne Bailon, whom he met around 2007. Bailon was often featured on early episodes of “Keeping Up with the Kardashians,” and the two seemed to be going strong until it was revealed that Kardashian cheated on her, causing the two to split in 2009.

Years later, a now-married Bailon admitted that being attached to the Kardashian brand due to a short-lived relationship has been a cross she’s accustomed to bearing. “It’s reality TV, and I used to get so annoyed by that, but I don’t now,” she explained to Us Weekly. “Now, I’m just like, ‘It is what it is.'” Appearing on the show seemed to cloud her other successes, including being a reputable artist and going on to be a popular television host on shows like “The Real” and “Masked Singer.” She reiterated, “I was like, ‘Guys, but I’ve accomplished other things’ … I just was annoyed that people tried to say that that was the only thing I had accomplished,” she asserted. “So that was a sucky spot in my career.”

But despite her challenges moving past her former ex, she still has a soft spot for the family. She told the publication that she still keeps in touch with Kim, and even watched episodes of “KUWTK” despite her history with Rob. “My executive assistant loves the show, and if we’re in the house, she’s like, ‘Can I put it on?’ And I’m like, ‘Sure, girl, go,'” she remarked.

Shortly after the dust between Ray J and Kim K settled, the reality star began getting close to Nick Cannon. The television host began dating the shapewear mogul in late 2006, but their romance didn’t quite go the distance. Eventually, the couple went their separate ways about a year later.

Cannon, whose gone on to be a successful television personality, artist, producer, and comedian, has since talked about his relationship with Kardashian in a good light. In an interview on “Drink Champs,” the rapper admitted that while she “broke his heart,” he doesn’t have a bad word to say about his ex-girlfriend. “We were kids, we were young,” Cannon noted. “I was really into her, I was vibing … [She’s] an amazing person.”

The host even claimed that he was the reason Kanye West first ran into Kardashian, after the two crossed paths at Cannon’s birthday party. The mother of four, however, has stated that she encountered Ye after her former boss, Brandy, collaborated with him on a track. “Long story short … we were getting pretty serious back then … I was hanging out with the family,” he stated.

After splitting with Kardashian, Cannon tied the knot with Mariah Carey in 2008, and they went on to welcome twins. The couple eventually divorced in 2016, and Cannon has since gone on to have several romantic relationships, fathering a total of 12 children with six different women.

With Nick Cannon out of the picture, Kim Kardashian didn’t stay single for long. The “Keeping Up with the Kardashians” star found love a few months later with then-NFL star Reggie Bush. Just after a year together, Kardashian was already gushing about her beau, telling People (via NBC), “I think I finally made the right choice. He’s just a really sweet, normal guy.”

The pair was often featured together on episodes of the reality show, but their relationship ran into difficulties when their respective busy schedules made it difficult for the two to spend time together. After managing long-distance for over a year, the two eventually split in 2009, but rekindled their romance not long after.

Kardashian and the former Saints player seemed to be head-over-heels after reconciling — even going house hunting together after getting back together. Their career constraints got in the way again, however, and the pair broke up again in 2010. Bush went on to marry his wife and professional dancer, Lilit Bush, in 2014, with whom he shares three children with.

Khloé Kardashian and Lamar Odom’s relationship was quite the whirlwind — especially since the pair wed just weeks after meeting in 2009. The reality star and the former NBA star weathered quite a few ups-and-downs over the years, many of which were featured on their spin-off reality show “Khloé & Lamar” which premiered on E! in 2011 and spanned two seasons.

Eventually, their marriage hit the rocks after rumors of Odom having a drug problem hit the press in 2013, along with reports of the former athlete being unfaithful. While the Good American founder had previously defended her then-husband over infidelity rumors, she ultimately filed for divorce in December of 2013. The move came just a few months after he sought treatment following a DUI arrest.

In the midst of their divorce proceedings, Odom continued to reach out to Kardashian in the years that followed. The reality star (who was still legally his wife at the time) was at his side in 2015 when he was found passed out in a brothel with alcohol, cocaine, and a sex stimulant in his system. Once Odom recovered, Kardashian moved forward with their divorce, which was finalized in 2016.

The former Los Angeles Lakers player has openly regretted his choices while married to the “Kardashians” star, writing about their tumultuous partnership in his 2019 memoir, “Darkness to Light.” In the book, he revealed that his former wife once called his friends over to have an intervention at their home when he was holed up in his room on ecstasy and cocaine. “Khloé came down and knocked on the door,” he recounted (via People). “I opened it suddenly and grabbed her forcefully by the shoulders, which frightened her. “What the f*** are you doing?’ I screamed, out of my mind,” he remembered. ‘You trying to embarrass me in front of my friends? I’ll f***ing kill you! You don’t know what I’m capable of!'” Odom has since repented, calling it the “most regrettable moment.”

Khloé Kardashian may have found a shoulder to cry on after divorcing Lamar Odom, but her newfound love with French Montana seemed to fizzle out as soon as it began. The two created a buzz in the Spring of 2014 after first been captured out together, and they went on to date for the next several months. The rapper and the reality TV personality eventually hit a rough patch in September of that year, however, with a source telling Us Weekly that “the relationship got too heavy and Khloe needed to take a step back.”

The couple was back on not long after, but, ultimately, their relationship couldn’t stand the test of time. “The rekindling has smoked out and they’ve moved on,” a source shared with E! News in December of that year.

While Montana has since been linked to several women in the music industry, including Rubi Rose, he has yet to confirm a serious relationship as of the time of writing. The “Unforgettable” artist is on good terms with Kardashian, however, articulating to Haute Living in 2019, “I feel like we had a real dope relationship. There was no bad blood, nobody did something to somebody that we couldn’t come back from. The love was real.”

It’s not exactly the best sign when an ex completely wipes you from their memory. Just ask Rob Kardashian, whose ex-girlfriend Rita Ora can’t remember dating him. The pair began dating in 2012, but were only linked for a matter of two months before they went their separate ways. When asked about it by The Sunday Times in 2020, the “Black Widow” singer admitted, “Oh, I forgot about that. It was very short-lived,” she offered. “I was so young. It was great. It was fun. It was very, very fun, I guess. That’s all I remember.”

As for Kardashian, he slammed Ora on social media after their break-up for cheating. “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,” the former sock designer wrote on X, formerly known as Twitter (via Us Weekly), after the split.

However, the “Poison” singer told The Daily Telegraph (via Today) that there were no truths to his claims. “I never thought it was actually a relationship, in all honesty,” Rita quipped. “I never mentally defined it as ‘boyfriend, girlfriend’. When I split up with him, I said, ‘It’s because I’m never there, I don’t know how to do it.'”

Harry Styles and Kendall Jenner have had a long-lasting friendship — that has sometimes crossed into romantic territory — for over a decade. The pair first sparked rumors in 2013 after they had dinner together in West Hollywood, and they were seen together on a ski trip with friends just a few months later. While the pair neither confirmed or denied whether they were an item in the years that followed, their close friendship seemed to turn into something more when they were spotted getting cozy in the Caribbean at the end of 2015 for that year’s New Years celebration.

Fast forward to 2017, and the former One Direction singer admitted that Jenner inspired much of his eponymous first solo album. In an interview for Rolling Stone, he elaborated, “She’s a huge part of the album,” adding, “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.”

Styles and Jenner both went on to date other people, but the pair remains on great terms. Fans even speculated that he blew the model a kiss in 2022 during a performance of his track “Love of My Life,” which is speculated to be inspired by her.

The way Blac Chyna fits into the complicated tale of Kardashian relationships is strange, to say the least. The model started dating Rob Kardashian around February 2016, but fans thought it was a bit weird that she would link herself to the former reality star after she previously dated — and had a son — with rapper Tyga, who was dating Kylie Jenner at the time.

The two managed to navigate the murky waters, however, and were given the family’s stamp of approval (or at least momager Kris Jenner’s). They got engaged after a few months of seeing each other, and announced shortly after the upcoming birth of their first child. Despite reports of a rocky relationship, the two welcomed their daughter, Dream, in the fall of 2016. After another year of on-again-off-again, the pair ultimately called it quits in 2017, but it wasn’t before Chyna went to war against the family.

The mother of two filed a defamation lawsuit against the Kardashian family in 2022, suing them for over $100 million dollars in damages. She claimed that the defendants were behind the cancellation of what was going to be a continuation of their “Rob & Chyna” reality series and damaged her reputation. Chyna ultimately lost the suit, however, and was awarded no damages as a result.

Kourtney Kardashian fell for Algerian model and boxer Younes Bendjima after their paths crossed in the most unlikely of ways. The Poosh founder ran into him at a Paris bar in 2016 the night before her sister, Kim Kardashian, was robbed at gunpoint, and he eventually acted as a French translator for the SKIMS founder after the scary ordeal. Despite the harrowing circumstances, he and Kourtney hit it off, and they began seeing each other seriously.

The couple seemed to be going strong for the next two years, with the model even meeting her children, but their relationship came to a head in 2018. The couple had reportedly taken a brief break at the time, but Kourtney ended things after photos of Bendjima canoodling with another woman in Mexico surfaced. Viewers caught a glimpse into the cracks in their relationship not long before that, when the athlete posted a criticizing comment on a photo of Kourtney in a thong bikini on Instagram. “Thats what you need to show to get likes?” he wrote at the time before deleting the comment (via Us Weekly).

Khloé Kardashian wasn’t Bendjima’s biggest fan, and even took to social media to air her grievances over her sister’s former beau. “He was sooooooo toxic and negative for Kourt. #KUWTK,” she wrote on X.

Kim Kardashian’s relationship with Pete Davidson began with an innocent kiss during a skit on “Saturday Night Live.” The show aired in the fall of 2021, and it wasn’t long before the public caught wind of a potential romance between the law student and the comedian. Their relationship began to speed up, despite the 13-year age gap, and Davidson eventually confirmed that Kardashian was his girlfriend that following February.

The couple weathered plenty of storms, with the biggest being the public disapproval of Kardashian’s ex-husband, Kanye West, but managed to make it a total of nine months together before calling it quits. “Part of the reason they split was because of their busy schedules,” a source revealed to People. “They both travel all the time and it was hard.” Davidson went on to date Madelyn Cline for about a year before they split in 2024.