The Kardashians may have an undeniable love for each other, but haven’t always been lucky in romantic love.
When Keeping Up With the Kardashians first aired, Kris Jenner and Caitlyn Jenner were the only married couple in the family. As the Kardashian-Jenners remained in the limelight, their relationship status has changed over the years. Many exes appeared on the show and on the family’s social media feed during that time.
Although some fans witnessed many Kar-Jenner relationships, many of them have become forgettable over the past 14 years.
Kim Kardashian and Damon Thomas
During the early seasons of KUWTK, Kim frequently opened up about wanting to get married and raise a family. On the show, she married former NBA player Kris Humphries. The star-studded wedding took place in 2011 and landed the couple a spinoff show, Kourtney and Kim Take New York.
After 72 days of marriage, Kim filed for divorce from Kris. Three years later, she and Kanye West married in 2014 had four children together. However, some fans might’ve forgotten that the KKW Beauty founder has walked down the aisle three times in her life. In 2000, at age 19, she married a music producer named Damon Thomas. At the time, he was 29.
Kim and Damon were married for four years before divorcing in 2004. Although she doesn’t speak much about her ex, the Skims CEO did share that she was high on ecstasy before her first wedding, per CNN.
“I got married on ecstasy the first time,” Kim revealed on KUWTK. “I did ecstasy once and I got married.”
Kylie Jenner and Cody Simpson
Long before Stormi Webster existed, Kylie Jenner kept her dating life as private as possible. In 2011, the youngest Kar-Jenner sibling quietly dated singer Cody Simpson. The pair met after Kylie flirted with Simpson on Ryan Seacrest’s radio show. The couple even received Kendall Jenner’s stamp of approval. However, the relationship only lasted a few months when they were teenagers.
After her split from Simpson, Kylie moved on to Jaden Smith in 2013. Then, she had public relationships with Tyga and her current boyfriend, Travis Scott. While Kylie hasn’t spoken about her past relationship with Simpson much, the Pretty Brown Eyes singer briefly addressed the breakup in 2014.
“The whole K-O-D-Y thing didn’t really work out for me,” he joked during an episode of Hello Ross, per People.
Khloe Kardashian and Rashad McCants
The Kardashian-Jenners have received accusations that they ruined the men in their lives’ careers on several occasions. West, Scott Disick, and Lamar Odom are some of the alleged victims of the “Kardashian Curse.” However, the sisters and Kris have vehemently denied those claims.
While many of the Kardashian exes speak of them in high regard, one of Khloe’s exes supported the Kardashian curse allegations. In 2008, she and the former NBA player’s 7- month relationship played out on KUWTK. On the show, Khloe accused McCants of cheating on her, resulting in their breakup.
In 2017, McCants addressed his relationship with the Revenge Body star with the Charlotte Observer. During the interview, he revealed that the relationship took a drastic toll on his basketball career.
“Without that situation in play, I’m a $60-70 million player,” McCants said. “Easily.”
Kendall Jenner and A$AP Rocky
Despite her admitted fondness for basketball players, Kendall briefly dated A$AP Rocky in 2016. According to Us Weekly, the pair were friends before deciding to give romance a try. Kendall and the “Everyday” rapper even shared a few PDA moments at the 2017 Met Gala.
Although they seemingly got along well, the 818 Tequila founder ended the relationship with Rocky. Soon, she and NBA star Blake Griffin attended dinner together in LA. However, Rocky reportedly didn’t mind, as the pair were never exclusive.
“Kendall and ASAP weren’t seeing each other a lot. They weren’t really official but were obviously dating,” a source said.“Their schedules are really hard.”
Kendall and Blake Griffin didn’t last, either. In 2021, the model celebrated her first anniversary with her boyfriend, Devin Booker.
Kourtney Kardashian and Luka Sabbat
Over the years, Kourtney Kardashian has had several romantic rumors. After breaking up with Scott Disick in 2015, she began dating model Younes Bendjima. The pair, who share a 14-year age difference, were together for a year before splitting up in 2019.
During the couple’s split, Kourtney started spending time with the model and actor Luka Sabbat. The Grown-ish star is 19 years older than Kourt. However, the couple vacationed together in January 2019 along with the rest of the Kar-Jenner clan.
“Kourtney invited Luka to come on the trip with them because he is friends with the whole group of girls, and she thought it would be fun. He’s been hanging around a lot, and Kourtney is always excited to see him,” a source told E! News. “Luka meshes really well with the group, and all of the sisters love having him around.”
Later that year, Sabbat confirmed to The Cut that he and Kourtney weren’t dating at the time.
Rob Kardashian and Rita Ora
Many KUWTK fans watched Rob Kardashian struggle to find love. In the earlier seasons, his romance with The Real host Adrienne Bailon played out for the cameras. The couple dated for two years before breaking up in 2009. Rob reportedly cheated on Bailon, which caused the split.
In 2012, the Arthur George CEO began dating Rita Ora. The pair were together for two months and ended due to Rob accusing Ora of infidelity. E! News published several tweets about the relationship and expressed how much his girlfriend hurt him. The tweets reportedly became so extreme that Khloe intervened.
Eventually, Ora and Rob moved on to other relationships. In 2015, he and Blac Chyna dated and engaged for several months. However, the couple, who welcomed their daughter Dream in November 2016, broke up that December. Eight years after his breakup with Ora, the “Body On Me” singer admitted she “forgot” they even dated.
“It was very short-lived,” she explained to The Sunday Times. “I was so young. It was great. It was fun. It was very, very fun, I guess. That’s all I remember.”
Kim Kardashian and Nick Cannon
Although they weren’t together for long, Nick Cannon still speaks about the time he dated Kim. The Skims founder dated The Masked Singer host in 2006. During their relationship, Kim worked for Paris Hilton and didn’t have her reality show yet.
In 2007, the KUWTK star’s life changed when her sex tape with Ray J leaked. When Cannon asked Kim about the video, he claimed that she lied and told him it didn’t exist. Once it came out, the talk show host broke up with the mother of four. However, Kim told Complex that the couple was never exclusive.
Even though they both moved on to other spouses, Cannon shared in October 2021 that Kim’s actions affected him deeply.
“I was really into her; I was vibing,” he admitted on Drink Champs. “We were on some serious s**t.”
“She broke my heart,” Cannon continued. “Then, it started being these rumors going around that it was this tape. When I asked her about it, she denied it.”