Dramatic breakups are one of the things that keep fans interested in the Kardashian/Jenner clan. As soon as one of the family members announces that they are involved with a new person, people start speculating about how long the relationship will last and just how dramatic the breakup will be. Many longtime Kardashian/Jenner fans feel that Kylie Jenner and Jordyn Woods‘ breakup is the family’s most heartbreaking dissolution.

Kris Jenner and Caitlyn Jenner breakup

When Keeping up with the Kardashian’s Kris Jenner and Caitlyn Jenner appeared to have a fairly stable relationship. They’d been together for quite some time and appeared to be happy. In comparison to the lives and relationships of the three Kardashian daughters, Kris and Caitlyn’s relationship seemed bland. It quickly became apparent that it was a case of what you see isn’t always what you get.

Rumors started to swirl that Caitlyn Jenner wasn’t completely happy with her life prior to her transition. In 2015, Kris Jenner officially file for divorce, stating irreconcilable differences and listing the official separation as 2013. Around the same time, Jenner announced that he was not happy living as a man and had decided to transition. At the time, the entire situation seemed both dramatic and heartbreaking. Today, both Kris and Caitlyn Jenner appear happy.

Kim Kardashian West and Kris Humphries

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Say hello to my little friend

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It’s hard to say if Kim Kardashian West and Kris Humphries were heartbreaking or just strange. The months leading up to the wedding were big news. The pair appeared to be in love, the wedding was considered “the event” of the year. A mere 72 days later, the pair announced that they were calling it quits.

The entire situation led to fans of both people involved to cry foul. Accusations flew that the pair had only wed for publicity. Even Kris Humphries seemed to have his doubts about the authenticity of the marriage. Their divorce wasn’t finalized until long after the two separated.

Kylie Jenner and Jordyn Woods

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the best gift of all 🖤

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Kylie Jenner’s various relationships have attracted a great deal of attention. She was heavily involved with Travis Scott, the man whom she shares a child with. Before Scott came into the picture, Kylie started spending a great deal of time with Jordyn Woods, the person she has long been calling her best friend. There was a long period when the pair was inseparable. That has changed. 

The break in the relationship took place when Jordyn Woods was caught in kissing Tristan Thompson. The problem was that at the time, Thompson was involved in what was believed to be a committed relationship with Kylie’s sister, Khloé Kardashian. Kylie promptly took her sister’s side and severed ties with Woods. Or did she?

There’s no evidence that Kylie and Jordyn are speaking, it’s surprising to many fans the two have stayed broken up as long as they have. Although many breakups in the Kardashian-Jenner family are heartbreaking, this one was different.

Fans who watched Life of Kylie know the two were practically sisters, and clearly loved each other. In Jenner’s early years as a reality star and makeup mogul, Woods was her rock. It’s heartbreaking to see two people who clearly cared for each other split, and it might just be the most heartbreaking split of the Kardashian-Jenner fam.

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