Are the Kardashian-Jenners unlucky in love? A closer look

If the reports are true, Kim Kardashian West and Kanye West are headed for divorce. That would make this her third. Since Kim and her famous family live their lives in front of reality TV cameras, their romances — for better or worse — are often very public. Those same relationships are dissected in good times and in bad, and with this family, there have been plenty of both. Considering all of their high-profile splits, is the Kardashian-Jenner clan unlucky in love? Keep reading to relive the sometimes unenviable love lives of the “Keeping Up With the Kardashians” stars…

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Many people forget that Kim Kardashian West was married as a teenager. The reality TV star wed music producer Damon Thomas in 2000 when she was just 19. The marriage actually lasted four years. “I got married on ecstasy,” she later said on an episode of “Keeping Up With The Kardashians.”  

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One of Kim Kardashian West’s most famous relationships was with Ray J — mainly because of what came out of it: a sex tape. Kim and Ray J dated from 2005 to 2007. Ray later claimed that Kim left her then-husband, Damon Thomas, for him. “After that, I felt obligated to be with her,” he said in his book, “Death of a Cheating Man: What Every Woman Must Know About Men Who Stray.” Kim said in a 2018 “Keeping Up With The Kardashians” episode that she was on drugs while filming the sex tape.

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Kim Kardashian West’s romance with superstar running back Reggie Bush was one that seemed like it might work out. The two dated off and on from 2007 to 2010. There were reports that Reggie and Kim were talking up until her second marriage.

Kim Kardashian West knew NBA player Kris Humphries for just 10 months when they tied the knot in a lavish wedding in 2011. She filed for divorce just 72 days later. Kim later told Bravo host Andy Cohen that she knew during the honeymoon that the marriage was over.

There had been rumors that Kanye West was romancing Kim Kardashian West for years — before, during and after her marriage to Kris Humphries. Eventually, Kim and Kanye dated and fell in love. The couple married in 2014 and now share four children. For the first several years of their marriage, all seemed well. However, it became clear in 2020 that things were unraveling, and Kanye even tweeted that he was considering a divorce. In late 2020, a report claimed that they were living separate lives as Kim spent most her time in Los Angeles while the rapper-designer was at his ranch in Wyoming. A few weeks later, just after the calendar switched to 2021, serious divorce rumors started to arise. Multiple media outlets reported that the duo’s marriage was hanging by a thread and that they were in counseling. Divorce, sources said, was absolutely on the table.

Khloe Kardashian hasn’t exactly had the easiest time finding long-lasting relationships. Khloe’s first high-profile love was NBA player Rashad McCants, whom she dated in late 2008. They even attended a Las Vegas party together on New Year’s Eve. They split in early 2009. Rashad later said the romance tainted his reputation and cost him upwards of $70 million.

Not long after her split from one NBA player, Khloe Kardashian was involved in a whirlwind romance with another basketball star, this time Lamar Odom. The pair dated for only a month before getting married in 2009. The couple launched a reality show together, and her family clearly loved him. In 2013, they split amid lamar’s drug and cheating scandals and Khloe filed for divorce. However, Khloe put the divorce on hold to care for Lamar after he suffered a near-fatal overdose in 2015. Once he recovered, they officially ended the marriage. Many fans always hoped they would reconcile, but it wasn’t meant to be.

Khloe Kardashian dated rapper French Montana on and off for a chunk of 2014. The two have remained close friends since their split. He even said they had “real love” during their relationship.

Say what you will about Khloe Kardashian, but the woman has a type. While caring for Lamar Odom following his overdose, the reality TV star dated Houston Rockets star James Harden (listen, the woman has a thing for NBA players!). The duo dated in 2014 and 2015. The split wasn’t exactly harmonious. In recalling the relationship, James called it “the worst year” of his life. There were also cheating rumors, something Khloe implied too. “I just don’t want to put up with people that you want to be monogamous but then they’re not monogamous,” she said on “Kocktails with Khloe.” That quote didn’t exactly age well. Keep reading to find out why…

In August 2016, Khloe Kardashian was linked to Cleveland Cavaliers star Tristan Thompson and soon, they were inseparable. She often traveled between Los Angeles and Ohio, where he lived. After about seven months of dating, she was publicly talking about being in love with the hoopster. Toward the end of 2017, reports claimed Khloe and Tristan were expecting a baby, which they confirmed that December. All was well — until he was caught kissing another woman at a New York City nightclub in April 2018, which occurred just days before Khloe gave birth. Then video from October 2017 surfaced in which Tristan was seen kissing and intimately touching two other women. Khloe was pregnant at the time of that incident too. They welcomed their baby girl, True, and Khloe forgave him as they worked through the scandal. Then in February 2019, Tristan was again accused of cheating, this time with Kylie Jenner’s then-BFF Jordyn Woods. Khloe quickly split with him. For months, he made flirty comments on her Instagram posts and tried to win her back to no avail. But as the coronavirus pandemic began in 2020, the two quarantined together for the good of their daughter. During that period, they reconciled. Again.

Since “Keeping Up With the Kardashians” began while she was young girl, Kendall Jenner grew up before the cameras. The model’s first public love interest of note was Harry Styles, whom she dated for a few months in 2013 and 2014 (and again in 2016). They remain friends.

In between 2013 and 2017, Kendall Jenner was linked to NBA player Jordan Clarkson and rapper A$AP Rocky, but there isn’t concrete evidence that either was a full-blown romance. The same can be said for NBA star Blake Griffin, whom she began dating in 2017. They were together for about eight months but eventually split in April 2018.

Kendall Jenner’s most serious relationship was easily with (you guessed it) another NBA player, this time Philadelphia 76ers star Ben Simmons. According to reports, the two began dating in July 2018. Kendall even confirmed the romance publicly, which was a rarity for her. She was soon attending a lot of his games, but distance took its toll and they split in May 2019. They soon reconciled, but that fizzled out. 

In April 2020, Kendall was linked to (stop us if you’ve heard it) another NBA player. Witnesses saw the model and Phoenix Suns stud Devin Booker on a road trip to Sedona, Arizona, in the early days of the coronavirus pandemic. Sources initially said they were “just friends” who ran in the same social circle, but it quickly became obvious there was more there. While Devin was in the NBA “bubble” in Orlando over the summer, the two exchanged flirty Instagram messages.

Kylie Jenner got her first taste of celebrity romances when she dated Cody Simpson back in 2011. Although they didn’t confirmed it at the time, a few years later, the Australian music star implied that the romance rumors were true. “The whole K-O-D-Y thing didn’t really work out for me,” he joked, referring to the family’s penchant for “K” names. 

In 2013, Kylie Jenner — then 16 — began showing up on Tyga’s Instagram. The following year, the rapper said the two were just friends, but photos proved otherwise (they wore matching Halloween outfits and attended parties together). Finally, after Kylie turned 18, the couple confirmed they were dating. He even got her name tattooed on his body and she called him her “husband” in an Instagram video. Things weren’t always great, and the duo split and got back together many, many times between 2015 and the spring of 2017, which is when they broke up for good. (Tyga would later imply that he was the father of Kylie’s daughter, which he isn’t.)

Shortly after splitting with Tyga, Kylie Jenner was linked to Travis Scott. At first, she and the rapper claimed they were just friends, but they couldn’t exactly keep that narrative when Kylie got pregnant. The couple welcomed a child, Stormi, in February 2018. Although the duo seemed in love, they split up in October 2019. Since then, there’s been regular speculation that they’re reconciling.

Kourtney Kardashian’s first serious romance is also her most well-known one. The eldest of the Kardashian sister met Scott Disick in 2006 at the home of Girls Gone Wild founder Joe Francis (who Kourtney briefly dated too). Kourtney and Scott immediately began dating and welcomed children in 2009, 2012 and 2014. The couple split up in summer 2015, but they’ve continued to co-parent. During their romance — much of which was on-camera — Kourtney and Scott tried couples counseling, grieved the loss of his parents and tried to work through Scott’s multiple rehab stints.

Kourtney Kardashian began dating model Younes Bendjima in late 2016 and they stayed together for nearly two years. According to Us Weekly, the duo split due to Younes’s immaturity. They made headlines thanks to their 14-year age difference. 

Kourtney Kardashian might have a thing for younger men (there was even a rumor that she hooked up with Justin Bieber!). Not long after the reality TV star split with Younes Bendjima, she began dating model Luka Sabbat (never mind their 19-year age difference). The two casually saw each other for a few months but ended things in October 2018. 

The matriarch of the Kardashian clan, Kris Jenner, hasn’t exactly had the best time in the love department either. According to reports, she began dating a golfer when she was 17 and he even proposed to her. However, by then, she’d left him for lawyer Robert Kardashian Sr. But they split while dating and Robert briefly started seeing Priscilla Presley. Kris and Robert soon reconciled and married in 1978. They had four children who reality TV fans are very familiar with. About a decade into the marriage, Kris had an affair with a professional soccer player, something she admitted in her 2011 memoir. Kris and Robert divorced in 1991. Robert famously defended OJ Simpson during the “Trial of the Century” in 1994 and 1995. The Kardashian patriarch passed away from cancer in 2003. 

After her divorce, Kris Jenner was set up on a blind date with an American icon, gold medal-winning Olympian Bruce Jenner. The two married in 1991 and had two kids, Kendall and Kylie. In 2014, the famous pair broke up and Kris filed for divorce. Her husband later came out as transgender. On June 1, 2015, Caitlyn Jenner made her debut on the cover of Vanity Fair. Kris and Caitlyn now rarely speak thanks to differing views on what was going on with Caitlyn’s gender identity during their marriage — drama that was chronicled on the family’s reality show as well as in Caitlyn’s book.

In the weeks following the finalization of her second divorce in 2014, Kris Jenner met and began dating Corey Gamble, who’s 25 years her junior (he’s actually younger than two of Kris’ daughters). In the beginning stages of their romance, the momager’s family was skeptical of the relationship, but they quickly warmed up to Corey. On his 40th birthday in 2020, Kris gushed over him. “Thank you for being the best partner, friend, confidant, therapist, advisor, travel star, and dance partner, and for always being there for my kids and my grandchildren. We all adore you,” she said. “I love you babe!!!”

Rob Kardashian publicly dated Cheetah Girls member Adrienne Bailon from 2007 to 2009. The singer and talk show host appeared on “Keeping Up With the Kardashians” multiple times during the romance. After they split, she accused him of cheating on her and he accused her of the same. She also got her Robert Kardashian tattoo, which was on her backside, removed.

In 2010, Rob Kardashian moved on with Angela Simmons. The pair dated long distance for a few months but ultimately broke up. It was an amicable split… seemingly one of the few.

Rob Kardashian’s brief romance with Rita Ora didn’t end well at all. The pair dated for two months in 2012. Following their breakup, he said she cheated on him with “20 dudes.” In 2020, she actually said she “forgot” she dated him. “Oh, I forgot about that,” she said when his name was brought up in an interview. “It was very short-lived. I was so young. It was great. It was fun. It was very, very fun, I guess. That’s all I remember.” Fun, but unmemorable… Not exactly good for Rob’s ego.

After several years of a downward spiral, which saw him gaining weight and becoming a recluse, Rob Kardashian surprised everyone when he announced in January 2016 that he and Blac Chyna were dating… the same Blac Chyna who has a child with Tyga, who was dating Rob’s sister Kylie Jenner at the time. Just a few months later, the duo got engaged and announced they were expecting a daughter together. After welcoming Dream, their romance turned and things got very, very nasty. They’ve both accused each other of domestic abuse and Chyna sued Rob’s entire family and alleged that they used their influence at E! to torpedo the “Rob & Chyna” reality TV show. She also said “racism” was a factor. Rob, meanwhile, once publicly accused her of abusing drugs and alcohol. He also posted photos of Chyna not wearing clothes on social media alongside incriminating captions. Since their 2017 split, there have been restraining orders filed and a custody battle. To this day, legal maneuvering between Chyna and the Kardashians continues.

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