Ranking The Kardashian Couples (Past & Present)

Telisa Carter

September 11, 2019

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The Kardashian/Jenner family has had an incredible rise to fame and after more than a decade in the spotlight thanks to Keeping Up with the Kardashians, it seems every move they make is documented. While fans have been obsessed with their business ventures, life changes, and everything in between, a main focus has been on the many relationships the members of the family have gone through. From flings, to marriages, to rumored hookups, here is every Kardashian couple ranked from least-liked to most-loved!

25. Kim Kardashian and Kris Humphries

Most Kim Kardashian fans still cringe when the name Kris Humphries is brought up. Kim’s second marriage was to NBA player Kris Humphries and right from the beginning fans knew something was off when the pair became engaged and tied the knot within 10 months of dating. When Kim filed for divorce after only 72 days of marriage, many were quick to call it a publicity stunt, but the Kardashian clan has always denied those accusations. Either way the relationship and marriage was awkward, confusing, and clearly not something either Kim or Kris wanted to be in.

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24. Rob Kardashian and Blac Chyna

Unlike most of the rest of his family, Rob Kardashian opted to stay mostly out of the spotlight, but that changed entirely in early 2016 when he began dating Blac Chyna. The relationship shocked everyone due to the fact Blac Chyna had previously dated and had a child with Kylie Jenner’s then-boyfriend Tyga. The complicated intertwining of the family’s love lives was bad enough, but it was worse when it became clear that Rob and Blac Chyna’s relationship was tumultuous at best, and there were concerns Blac Chyna was only in it to tie herself to the Kardashian fame. Unfortunately, it worked as the pair were engaged only three months after date and one month later it was revealed they wer expecting a child together.

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23. Kim Kardashian and Damon Thomas

In all fairness, Kim Kardashian and Damon Thomas’s relationship came before her fame, but it is still important to her life as her first marriage. In 2000, at only 19, Kim eloped with the music producer but after three years of marriage he filed for divorce. Kardashian said later that she suffered emotional and physical abuse during their three year marriage and claimed she was on ecstasy during the ceremony. It seems like the relationship was anything but healthy, which makes them one of the least-liked couples on this list.

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22. Kylie Jenner and Ramsey IV

Kylie Jenner was always a little more private her earlier relationships and since fans don’t really know much about her first ever romance, it lands pretty high on the list. Ramsey IV was Kylie’s first boyfriend from when she was 12 years old and they dated for about three years. Although there are many rumors that Jaden Smith was actually her first love, they have never confirmed they were anything more than friends. While there was nothing wrong with Kylie and Ramsey IV’s relationships, it was before she was in the spotlight and fans really got to know her, landing it at number 24.

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21. Brody Jenner and Josie Canseco

Brody Jenner has flitted in and out of the spotlight, but did so away from his famous family. After his time on The Hills, Brody made his return to reality TV with The Hills: New Beginnings where his relationship with wife Kaitlynn Carter was front and center. After their sudden split, Brody was quick to hook up with model Josie Canseco and for now it just seems like a rebound and a way for Brody to get back at his ex.

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20. Khloe Kardashian and Lamar Odom

There is no denying that Khloe Kardashian and Lamar Odom’s relationship was a bit of a train wreck from start to finish. Fans wanted to see Khloe happy, but knew almost right away it wasn’t going to be with Lamar. The whirlwind relationship started in the August of 2009 and only one month later the pair were married, and many already questioned how genuine the romance was especially with the wedding featured as a “special event” on KUWTK. Unfortunately, Odom’s infidelity caused the end of their relationship and it caused Khloe a lot of heartache and sadness. While they certainly were not compatible as a couple, the pair have shown how much they truly care about each other when Khloe stayed by Odom’s side during his recovery after his near-fatal overdose in 2015.

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19. Brandon and Leah Jenner

Brandon Jenner is the son of Caitlyn Jenner and Linda Thompson and seemed to shy away from the spotlight that came with his father’s relationship with Kris Jenner and Brandon’s extended family. Brandon married Leah Jenner in 2012 and fans loved the duo as they focused on their indie pop music under the name Brandon & Leah. Along with their two children, Brandon and Leah seemed like the perfect family, but many didn’t know that much about them. After several years in what seemed like happiness the two shockingly announced their separation in September 2018 and Brandon is now expecting twins with his new girlfriend.

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18. Khloe Kardashian and Tristan Thompson

Everyone knows that Khloe’s relationship with Tristan Thompson ended terribly, but at first fans were ecstatic that seemed for the first time Khloe was truly happy and found someone she really wanted to settle down with. When Khloe got pregnant, it seemed fantastic as she had always been open about wanting to be a mother and Thompson seemed like a guy who would be there for her. Of course, now it is clear that Thompson isn’t that guy and the multiple high-profile cheating scandals were devastating and while fans loved the couple together at first, Tristan Thompson is now one of the most hated Kardashian exes out there.

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17. Kim Kardashian and Ray J

Following her marriage, Kim Kardashian’s next major relationship was with rapper Ray J. The pair met when Kim was working as assistant for Ray J’s older sister Brandy and the pair dated on and off from 2005 to 2007. Yet again, this relationship happened before Kim had a huge fanbase and was in fact working as an assistant to other celebrities, but it isn’t exactly a disliked relationship. Kim and Ray J’s relationship and of course infamous tape has been credited for catapulting the popularity of Kim Kardashian and by association Keeping Up With the Kardashians, and of course the rest of the family.

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16. Scott Disick and Sofia Richie

After years of an on-again, off-again relationship with Kourtney Kardashian, Scott Disick has been linked to several different women. Eyebrows were raised however when he was said to be dating Sofia Richie back in May of 2017 when she was 19 and he was 34. While many didn’t expect the relationship to last, especially with a 16-year age gap, the couple have continued to surprise everyone with the seriousness and longevity of their romance. It has gotten to the point where an engagement is expected and despite having been together for a couple of years, many are still taken aback by the relationship.

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15. Kris Jenner and Caitlyn Jenner

When Keeping Up With the Kardashians first aired, Kris Jenner and Caitlyn Jenner (then Bruce Jenner) were a power couple of Hollywood with their large blended family. The pair were married in April 1991 and welcomed Kendall and Kylie before reality TV took center stage in the family. Kris and Caitlyn were one of the funniest couples on the series with their different personalities trying to lead their family. Many were surprised when the pair announced their separation in 2013, and fans learned of Caitlyn’s gender transition in 2015 after months of rumors. Despite a major shakeup in their relationship, the two have remained friendly and Kris has always supported Caitlyn.

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14. Kourtney Kardashian and Younes Bendjima

After Kourtney Kardashian’s nearly 10 year on-again, off-again relationship with Scott Disick, fans were surprised and thrilled to see her dating someone new in model Younes Bendjima. The two were first linked in 2016, and were quickly seen spending time on yacht together, taking a trip to Egypt and attending events together. It seemed as though Kourtney was finally enjoying dating after so many ups and downs with Disick, and while it was fun, fans didn’t see Younes as anything other than a rebound for Kourtney.

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13. Brody Jenner and Kaitlynn Carter

After The Hills came to an end, Brody Jenner slowly filtered out of the spotlight and not much was known about his relationship with Kaitlynn Carter. That all changed when both joined MTV’s revival of The Hills with The Hills: New Beginnings, and viewers got an inside look at their life. Almost immediately, many were shocked by how Brody discussed marriage and it sadly wasn’t that surprising when the pair announced they had separated after The Hills: New Beginnings had begun to air.

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12. Kourtney Kardashian and Scott Disick

One Kardashian couple that always baffled fans was Kourtney and Scott Disick. The pair’s tumultuous romance had fans both rooting for them and against them at alternating moments. At times Kourtney and Scott seemed like the perfect match, and other times it seemed as though a committed partner and three children was the last thing Scott wanted. Although most hoped the pair would make it for the sake of their family, it didn’t seem likely, and by the time the pair officially split in 2015 many were relieved that it was finally over after countless breakups and makeups.

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11. Kylie Jenner and Cody Simpson

Kylie Jenner and Cody Simpson had a brief romance in 2011 and since it was before Instagram and Kylie’s major celebrity status, not a lot is known about them as a couple. What is known is that the two did date briefly before Simpson’s high-profile romance with Gigi Hadid, and the Australian singer actually joked about his short-lived romance during an appearance on E!’s Hello Ross. “No, the whole K-O-D-Y thing didn’t really work for me,” he said. It may not have lasted long, but it was adorable while it did.

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10. Rob Kardashian and Adrienne Bailon

In the early years of KUWTK, Rob Kardashian and Adrienne Bailon were one of the most popular couples! Even though more than a decade has gone by since the pair dated for only two years, many are still obsessed with the romance. During the romance, Rob didn’t shy away from the spotlight as much and fans watched his heartbreak as Bailon left to film a movie for three months. Their love truly seemed genuine even with the traction the show was getting, and it was upsetting when Rob admitted he cheated on Bailon during their relationship and the two split for good.

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9. Kendall Jenner and Ben Simmons

It has been incredibly difficult for fans to detect Kendall Jenner’s relationship status. Unlike the rest of her family, Jenner rarely if ever comments on relationships and romances and often passes most off as just friends hanging out. Kendall has been linked to A$AP Rocky, Nick Jonas, Blake Griffin, and Anwar Hadid just to name a few, but one relationship that seemed to be for real was with NBA player Ben Simmons. The pair seemed to be getting pretty serious throughout 2018 with Kendall often rooting Simmons on courtside. In May, the two reportedly broke up, and fans are already trying to determine who the model is dating now.

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8. Khloe Kardashian and French Montana

Following Khloe’s split from Lamar in 2013, she began dating French Montana in July 2014 after they were introduced in 2014. For the most part the two were happy and supportive of one another and Montana seemed a lot less dramatic than Khloe’s previous relationships. Fans were extremely supportive of the relationship because it seemed that Khloe was moving on and finding her happiness again. Most didn’t think that the pair were going to last forever, but he was exactly what Khloe needed at the time.

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7. Kris Jenner and Robert Kardashian

To be fair, fans of the Kardashian family never really got to know Kris Jenner and Robert Kardashian as a couple, but it is clear that the two had a very special relationship. The famous lawyer and Kris Jenner were married in July 1978 and were married for over 10 years and welcomed their four children before they divorced in March 1991. Despite their split, the two proved how close their bond was as they stayed friends until Robert’s passing in 2003. Over the years, Kris has always remembered her late ex fondly and Kourtney, Kim. Khloe and Rob have been open about a great childhood they had with both of their parents.

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6. Kylie Jenner and Tyga

Kylie Jenner’s relationship with rapper Tyga, whose real name is Micheal Ray Stevenson was endless tabloid fodder for its entire three year duration, and opinions on the romance were mixed. Many were not impressed with the fact that the pair initially met when Kylie was only 14 and Tyga was 21. Because of the age gap the two kept their romance quiet before finally going public when they celebrated Kylie’s 17th birthday but maintained they were “just friends” until Kylie’s 18th birthday. Despite issues with the age gap, many supported the relationship as the two stuck together through many rumors and alleged scandals, and Kylie seemed to handle her relationship in the public eye with maturity. Unfortunately, the end of their relationship brought drama and it was clear the two weren’t meant to be despite plans of marrying.

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5. Kendall Jenner and Harry Styles

Young fans around the world erupted when two of the biggest young celebrities Kendall Jenner and Harry Styles began dating., The two first grabbed dinner as “just friends” in 2013 but were linked again in 2014 when they were seen skiing together. Despite continuous reports it was never anything serious, the two vacationed together again in December 2015 where they were spotted being cozy on a yacht. Kendall Jenner has always been much more elusive about her relationships than a lot of her family, but whether they were officially dating or not, there is no denying that fans loved Kendall and Harry Styles together.

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4. Khloe Kardashian and James Harden

In the beginning, everyone loved Khloe Kardashian with NBA player James Harden. Unlike some other athletes Harden seemed down-to-earth and mature, and almost the perfect fit for Khloe who had been searching for a mature relationship. The two began casually dating in 2015 before it turned more serious at Harden’s insistence. Separate lives in Houston and L.A. didn’t seem to phase the couple until it was revealed that Harden had cheated on Khloe. Before the cheating, the two were actually a great couple and many were extremely disappointed in Harden’s infidelity.

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3. Kris Jenner and Corey Gamble

Kris Jenner is the ultimate “momager” and while she is a prominent force in her daughter’s careers and on Keeping Up With the Kardashians, Kris Jenner is also skilled at working behind the scenes. Although she has made several appearances with her boyfriend Corey Gamble, little has been known about their relationship over the past few years. The pair started dating presumably around 2014 and despite concerns about their age difference, everyone is just happy that Kris is in a loving and committed relationship. “He’s such a nice person. She can connect with him and go to movies with him, work out with him. It’s the little things. It’s been so much fun just to see my mom happy. It’s been refreshing to see her have a good time,” Kim has said of her mother’s relationship.

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2. Kim Kardashian and Kanye West

After her marriage to Kris Humphries, Kim Kardashian took a lot of criticism for her romance with rapper Kanye West. Kim had brief relationships with stars including Nick Lachey and Nick Cannon as well as athletes like Reggie Bush and Miles Austin before dating West and many believed it was just another relationship to get her into the spotlight. It turns out, Kim and Kanye are the real deal as the pair were friends for around 10 years before they started dating in 2012. Following their May 2014 wedding the famous duo have welcomed four children, and have proved their critics wrong as they have focused on a happy, and healthy life for their family.

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1. Kylie Jenner and Travis Scott

Following her split from Tyga, Kylie was linked to several other rappers and celebrities before getting close to Travis Scott at Coachella in April of 2017. Since then the pair have been inseparable as Kylie decided the night of his Coachella stop that she was going to pack up and go on tour with him. Before long pregnancy rumors swirled as they had many times while she was with Tyga, but this time it was true! The couple have since welcomed daughter Stormi Webster. Despite extremely busy and hectic lives both together and individually in the spotlight, Kylie Jenner and Travis Scott have formed a very solid family unit and many respect how private they keep their relationship despite their level of fame. The pair are so private, they might already be married!

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Telisa Carter

Telisa enjoys learning and writing about all things entertainment in the world of Hollywood. When she isn't catching up on her favorite TV shows, she likes to read, and obsess over all things football.