No one knows how to keep us entertained quite like the Kardashians do. Ever since the first episode of Keeping Up With The Kardashians aired, the most famous sisters in the world built a multimillionaire empire based on putting their entire lives out there for the world to see – and the public happily took what was given.
Undeniably, most of the entertaining bits related to the sisters stem from their love lives. There’s something for everyone, whether it is cheating allegations, 72-day marriages, or unexpected pregnancies, the Kardashian-Jenner clan don’t seem to know peace in their romantic relationships.
With all the sisters more than grown-up and the youngest being crowned the youngest self-made billionaire ever, it’s more than the time we rank their relationships, from worst to best. For clarity purposes, very short flings, or romances that happened at very young ages (as is the case of Kylie and Jaden Smith) will not be considered for this list.
11Khlóe & Tristan Thompson
This one was a doozy. Obviously, our hearts go out to Khlóe, who thought NBA player Tristan Thompson would finally be it for her, after all the terrible things she had to endure with her previous partner (more on that later). When the two were first linked together, back in late 2016, and then confirmed their relationship, in 2017, Khloé was quick to tell the world how in love she was, even though rumors were flying around that Tristan cheated on his baby mama with Khloé.
In early 2018, news broke that Tristan Thompson cheated on a pregnant Khloé, but she decided to put everything behind in order to create a safe environment for daughter, True. That didn’t last long, and tensions between Thompson and the rest of the Kardashian family were as high as ever. The sisters seemed to be right, and an even bigger cheating scandal rocked the couple when it was reported Tristan kissed Kylie Jenners BFF Jordyn Woods. Since then, Khloé called it quits for good, and this relationship will go down in Kardashian-Jenner history as the worst ever – but at least it gave Khloé the gift of baby True.
10Khlóe & Lamar Odom
Khloé wasn’t very lucky in the love department, at least where the last decade is concerned. Before the dawn of cheater Tristan Thompson, there was Lamar Odom, and the two seemed like the perfect match – they were so cute and loving, they even got their own TV show on E!, Khloé & Lamar, and launched a unisex fragrance together, after being married for a year.
In 2012, it all came crashing down. There was speculation that the couple’s fertility problems were at the root of the impending split, but soon, cheating allegations against Lamar began surfacing. Eventually, it went public that Odom was addicted to drugs, and when he posted a video rapping about cheating on his wife, Khloé finally filed for divorce in 2013, after four years of a very rocky marriage.
9Kim & Kris Humphries
The whole thing screamed disaster from minute one. The two got engaged after only seven months of dating back in 2011, and the entire process was scrutinized by the media and heavily monetized by the Kardashian family. The wedding was one of the biggest events in the history of the family, lavish from top to bottom, even though the two simply didn’t seem to fit together as a couple.
Predictions from Kim’s family members, including sister Khloé, turned out to be true, and the pair called it quits when Kardashian filed for divorce only 72 days after they were wed in California. To this day, many believe the whole thing was nothing but a publicity stunt to make money, but both parties have denied it, with Kim even suing one of her former publicists, who backed the claims at the time.
8Kim & Ray J
This relationship will forever be remembered for its ultimate outcome, a scandal of epic proportions that rocked the Kardashian family to the core, and had a major role in putting all the sisters, but especially Kim, in the spotlight. We’re obviously talking about the tape that got leaked back in 2007.
Before everything went down, the pair were linked together in the early 2000s, when Kim was working as an assistant to Ray’s sister at the time. The two had an on again, off again relationship for two years, from 2005 to 2007, and by the end of the affair, the now infamous tape was leaked to the public. Not the best way to part, but the two seem to have moved on from the whole ordeal.
7Kylie & Tyga
Tyga was Kylie’s first serious relationship, and much like Kim and Reggie, there was a time the two thought about getting married one day. It was a very entertaining relationship for anyone watching from the outside, and although the two seemed happy, lasting for three years, there were some extremely questionable moments.
When the two first met, Kylie was only 14 years old, and Tyga was already 21. In 2014, three years later, the rapper showed up on Kylie’s Instagram and broke off his engagement to Blac China, his baby mama, who later went on to begin a relationship with Jenner’s brother, Rob, and have his child – straight out of a soap opera.
They denied the relationship until Kylie celebrated her 18th birthday, and the two stayed together until 2017, after their fair share of public break-ups and reconciliations. Eventually, enough was enough, and Kylie moved on to better things.
6Kourtney & Younes Bendjima
After calling it quits for good after a heck of a rocky relationship with her baby father, Scott, who had recently started dating Sophia Richie, older sister Kourtney started being spotted on several occasions getting cozy with model Younes Bendjima in mid-2017.
They seemed super in love, and traveled the world together, going from one romantic destination to the other, touching upon places such as Egypt and Mexico. Many criticized Kourtney for the age gap between her and her new boo (he was 24 when they started dating, she was 38), but the pair didn’t seem bothered at all.
However, when in 2018 Younes left a less than impressed comment on one of Kourtney’s Instagram snaps, rumors started surfacing the two were splitting up. Soon after, pictures of the model getting cozy with Jordan Ozuna, and it was confirmed the pair had officially split, among rumors Younes had cheated on Kardashian. Yikes!
5Kim & Reggie Bush
Before dating, and eventually marrying, and eventually divorcing (rocky roads, indeed), athlete Kris Humphries, Kim was in quite the serious relationship with American football player Reggie Bush, and there were even talks about the two someday tying the knot.
One of Reggie’s teammates introduced him to Kardashian, and the two started dating in 2007 and seemed to be going quite strong for the next two years. Unlike many of the Kardashian-Jenner relationships, these two were rarely plagued by drama or scandal. Whether or not that was their downfall, the two eventually split in 2009, and although they tried to give it another go a few months after, the relationship never seemed to take off again, until they called it quits for good after the Superbowl in early 2010. It just wasn’t meant to be!
4Kourtney & Scott Disick
Where to even begin with these two? They are the textbook definition of a rocky road, and if they hadn’t called it quits, who knows where they would be now? (Probably stuck in a cycle of mutual destruction). Kourtney is the sister with the longest relationship, having dated the father of her three children for nine years. Impressive record!
Scott’s continuous substance abuse, heavy drinking, and wild partying habits plagued the couple from very early on. The two broke up in more than one occasion due to Scott being spotted several times with different women on crazy parties, even after the couple’s first child was born. In 2015, Kourtney finally had enough, and the two broke up for good.
Disick always maintained an incredibly tight relationship with the entire family, and even though they are no longer together, Kourtney and Scott put a lot of effort into co-parenting their children, and seem to have a genuinely tight bond of friendship, which would be expected after over a decade of knowing each other, and three kids together.
3Kim & Kanye West
It’s honestly quite hard to remember a time when Kimye wasn’t a thing, and that alone says a lot about how iconic they are. The pair have actually known each other since 2003, and Kanye has stated that ever since he laid eyes on Kim, he knew he wanted her for his own. He had to do quite a bit of waiting, but things turned out for the best!
Just in case you’re wondering how serious his feelings for Kim were when it was announced she was marrying Humphries, Kanye got a cellphone to try and keep the whole thing from happening. That’s some commitment right there, and while it didn’t work out immediately, he eventually got what he wanted.
The two started dating officially in 2012 and welcomed their first child, North West, in 2013. A few more would follow, alongside a beautiful wedding ceremony, a steamy music video, and a Vogue cover. Kanye isn’t the easiest personality to deal with, but Kim seems like a perfect match for him, through and through.
2Kendall Jenner & Ben Simmons
Kendall is definitely the most discrete out of all the sisters, both in terms of personality and love life. Jenner seems to enjoy her privacy and low-key life very much, and little is known about her past relationships and flings. While she has been tied to many people in the past, there’s one in particular that has been going on recently fans are enjoying very much.
Basketball player Ben Simmons marks the first time ever Kendall confirmed to the public she’s dating someone, and according to several sources, the two are in a full-blown, committed relationship. She frequently attends his games, and when the two are spotted together on the street, they look just like your typical stylish, laid back, happy couple. We can’t wait to see what the future will bring for these two!
1Kylie & Travis Scott
They could very easily be deemed the celebrity definition of the ultimate relationship goals. And while they haven’t been together for too long, these two seem solid as steel – and we’re sure having a beautiful baby daughter helps.
Kylie and Travis were first spotted together very soon after Jenner called it quits with ex Tyga, but that didn’t keep them from falling head over heels for each other, with Kylie deciding to follow him on tour when they were still getting to know each other. One thing led to another, and the couple welcomed their first child in February of 2018, and have been rocking red carpets and magazine covers ever since.
Travis’ odes to his baby mother in his music are plentiful, and rumors have been circling around for ages that the two are either engaged or have already married in secret. Although their relationship is one of the most scrutinized out there, somehow the pair seem to make it work wonderfully.
