Inside Kylie Jenner's Impossible Struggle: Why She's Having a Hard Time Letting Go of Jordyn Woods

Khloe Kardashian's decision to break things off with Tristan Thompson may have been clear cut, but it's been far tougher for her little sister to dispense with her other half.

By Sarah Grossbart Feb 25, 2019 9:03 PMTags
Jordyn Woods, Kylie Jenner, InstagramInstagram

Even in the middle of an intense personal crisis, Kylie Jenner is a savvy—and, at times, savage—businesswoman. 

So faced with the increasingly apparent truth that her longtime bestie, Jordyn Woods, had, in fact, hooked up with Tristan Thompson, sister Khloe Kardashian's boyfriend of two-and-a-half years and daughter to her 10-month-old True Thompson, well, she had to act. 

And by the afternoon of Feb. 21, not even 48 hours after the first reports leaked that the unlikely couple had been appearing decidedly intimate while hanging at Thompson's L.A. pad, Woods was relegated to the discount bin. Quite literally. The Kylie Cosmetics founder slashed the price of her $27 Jordy Velvet Lip Kit, marking the raspberry-hued liquid lipstick and liner, first released last May, as one of the sites "best values." 

Naturally, it sold out immediately. 

Kylie Jenner and Jordyn Woods' Friendship Through the Years

Woods' personal stock, however, could best be described as crumbling. 

Khloe's decision to cut Thompson loose after hearing from multiple friends that the Cleveland Cavaliers center, 27, flirted with 21-year-old Woods at a Santa Monica bar Sunday night, then invited her back to his house where they proceeded to cuddle and make out in full view of their fellow guests was only the first major breakup of the week. 

In what was, perhaps, a more shocking split, Kylie "completely cut off" Woods, her close pal since eighth grade a source told E! News, asking the model and clothing designer to vacate the guest house at her impeccably decorated Hidden Hills, Calif. spread and leave the keys behind. "Kylie's life has been turned upside down," continued the source.

This is someone she's described as her "only friend", someone she considered to be family and with nearly a decade of history between them, closing that door felt unfathomably painful. And, yet, some situations require decisive action and for the 21-year-old, at this moment it was necessary to show support for her biological sister, the one who held her hand as she delivered daughter Stormi Webster last February and has never given reason to question her motives. As she absorbs what can only be described as a colossal shock, said the source and wrestles with whether to give Woods another chance, "She feels like she never knew who Jordyn was." 


Though the basketball player's latest betrayal is one of epic proportions—cheating on the mother of your child with one of her closest family friends on Valentine's Day weekend is decidedly low—few would say he and the reality star were on solid footing before this latest lapse in judgment. 

Truthfully, their years-long romance never fully recovered from his last misstep. Caught up in a web of cheating reports (some accompanied by videos of him at clubs and outside a hotel) mere days before Khloe gave birth last year on April 12, his acceptance back in the fold was always conditional. Understandably hurt, the 34-year-old new mom nonetheless made the difficult decision to give him another chance for the sake of their burgeoning family. 

"Things are more complicated now that there is a child involved, but it was causing more stress on Khloe by being in limbo with Tristan," a source explained last May of her choice to move forward. "Khloe decided that the back and forth and indecisiveness on what they were going to do was taking a toll on her."


Her biggest worry, said the source, was not whether she could get past his treachery, but the fear he might dare do it again. "She wants to make sure she is not embarrassed and heartbroken again, but everyone is warning her," detailed the source. "Khloe has a huge heart and once she falls, it's hard for her to give up on someone she cares deeply about. She has been in a rough spot this past month."

To assuage some of her, and her family's misgivings, she made it clear to the Toronto native exactly what type of behavior would not be tolerated, with the source telling E! News, she "definitely set guidelines and boundaries for their new chapter."

A happily ever after, though, remained out of reach. As Khloe grew more comfortable parenting True, a blessing she's said she dreamt about "my entire adult life", and building a life for them near her family in L.A., she saw less of a need to return to the home she'd created with Thompson in Cleveland. 

True Thompson's Cutest Photos

Their romance "never really went back to normal," a source told People and she found herself keeping Thompson at arm's length. "The only reason she was still seeing him was because of True." While the trio spent the holidays as a family, in an effort to start new traditions together, and rang in the New Year side-by-side, Khloe hadn't made the trek back to Ohio in two months. And the last time she'd been photographed with Thompson was when the Cavaliers were in town Jan. 13 to take on the Lakers. 

Whether or not the pair split before Thompson's tryst with Woods is a bit murky, but the final result is clear: "She gave Tristan everything she had and she isn't going to do this to herself anymore. She knows she deserves better," an insider told E! News. "She has never trusted him again and its been an awful way to live. She is done."

Kylie's breakup, however, was less cut and dried. If Khloe's romance with Thompson was shaky, her bond with Woods could best be classified as rock solid. The pair were so tight, that the makeup maven alternated between referring to Woods as her sister and as her wife, the two having held a commitment ceremony in Peru that aired on 2017's Life of Kylie.

The aim, Kylie explained was to demonstrate that their connection extended far beyond friendship. "I want people to know we're more than that," she noted. "She's my girlfriend. I care for her like I care for my girlfriend." 

Woods vowed "to always be there" for Kylie, "through thick and thin." The youngest Kardashian-Jenner sibling, in turn, pledged "to encourage you, inspire you, love you, through all the good and bad times." 

And for a while there it seemed each had taken their words to heart. 


When Kylie suspected that she may be with child just weeks into her romance with Travis Scott, 26, it was Woods who was at her side when she took a pregnancy test. "One day, I was in your mom's bathroom with her," Woods shared in the epic 11-minute video Kylie created as a tribute to her daughter, "and she took a little test...and then she passed it to me after, like, 'surprise.'"  

With Stormi's 2018 arrival, Woods took on the role of a second mom, tagging along when mother-and-daughter traveled to Miami and Turks and Caicos to offer up another set of hands. "Jordyn is basically a third parent to Stormi," a confidante told E! News, "and was her biggest supporter for all of Kylie's major life moments." 

And Kylie was every bit as generous. Not only did she offer Woods a spot in her outsized pad, but she gifted her with a car, vacations and opportunities aplenty. 

She and the L.A. native collaborated on a line for her near-billion-dollar Kylie Cosmetics brand, the announcement of the Kylie x Jordyn collection of glosses, lipsticks and eyeshadows with names such as Don't Ever Leave Me and Loyal touting their "true unmatchable relationship". 

Keeping Up With Jordyn Woods

Woods also modeled for Khloe's Good American denim label and when she decided she wanted to launch a brand of her own last August, a size-inclusive activewear line called SECNDNTURE, inspired by her increased devotion to fitness, Kylie was there to provide her marketing expertise. 

"As of two days ago, I hadn't posted anything, so Kylie was like, 'You need to blow up Instagram. You want me to go on your phone and post?'" Woods told Fashionista. "I was like, 'Calm down, I'll do it.'"

Now she'll be handling a lot more on her own. 

Back at her mom's California pad and desperately trying to shore up those in her circle of friends not connected to the Kardashian-Jenner clan, "Jordyn is living her worst nightmare," an insider told E! News of Woods, who did her best to fly somewhat under the radar while out in West Hollywood last week for the launch of her lash collaboration with Eylure. "She's completely distraught and knows she has lost everything. Her life will never be the same."


The same could be said for Kylie, who was initially left wavering on how to best handle the tidal wave of emotion. 

At first, an insider told E! News, she struggled to believe it was even true. Surely, her closest friend wouldn't conspire to hurt her sister in this way and everything could all be written off as a case of mistaken identity. "She wanted to give Jordyn a chance to explain herself," said the insider. "She doesn't know what to do. She's shocked and confused. Jordyn has been another sister to her and has been by her side at all times. She can't imagine life without her."

But as more friends confirmed what happened—a source told E! News Woods and Thompson met up during a night of drinking and took their flirtations back to his house where they "sat together and cuddled for hours,"—she knew the tough call she had to make.

A History of Khloe Kardashian and Tristan Thompson's Relationship

Not only had Woods betrayed her, but she'd intentionally hurt Khloe, a woman who had trusted her both with her Good American brand and her rawest of emotions.

"Jordyn was a friend that Khloe confided in about her difficulties with Tristan and then Jordyn did this," says a source. The model had even publicly defended Khloe's decision to stay with the father of her child, telling Us Weekly, "I think they just have fun together. I feel like they have great chemistry, so that works out well." 

But now there are no words she could come up with to make this situation go away. While a source tells E! News Woods has been placing frantic phone calls to Kylie, Khloe and even family matriarch Kris Jenner, desperate to explain her wrongdoings, she's been essentially frozen out for the time being. 

"The family won't be forgiving," said one insider. "They have done everything to help Jordyn be successful on her own. They feel she would be nothing without them. It's such a betrayal for them."

And though it's been much more of a struggle for Kylie to excise her closest companion, right now, says a source, "She is done."

Jordyn Woods/Instagram

Because in the end, while Woods was able to talk the talk when it came to true friendship, her actions haven't matched up. 

Explaining how vital it was to have a bestie like Kylie, she told reporters at a 2017 World Smile Day celebration, "I feel like it's important that you have the same understanding with your friend. You both have the same understanding and you know that I can trust this person, and I'm not going to do this, and that person is not going to do the same. Honestly, you can't really trust anyone. You really can't. People stab you in the back all the time." 

In that moment, Woods couldn't have possibly known she'd one day be the person left holding the knife, but it's an image that Kylie feels she can't escape. "It's all just a huge shock and shows her true colors," a source told E! News. And should the besties one day reunite, there will be a lot of rebuilding to tackle. Noted the source, "It's going to take a long time for the sting and the shock to go away."