Inside Kylie Jenner and Jordyn Woods' Once "Unmatchable Relationship"

Inseparable since meeting in middle school, Kylie is "devastated" over the allegations about her BFF whom she considers another sister and Tristan Thompson hooking up over the weekend

By Tierney Bricker Feb 20, 2019 10:00 PMTags
Watch: Khloe Kardashian and Tristan Thompson Break Up

One of the Kardashian family's longest running relationships might be in jeopardy.

No, we're not talking about any of the romantic ones; we're talking about the "unmatchable relationship" between Kylie Jenner and her longtime BFF Jordyn Woods, which is now being tested in the wake of the shocking news that Jordyn, 21, may have hooked up with Tristan Thompson, Khloe Kardashian's boyfriend and the father of her infant daughter, True Thompson.

A source close to the family told E! News "Khloe is more disappointed that someone so close to their family would betray her," but it's Kylie, 21, that is "in denial" over Jordyn's alleged actions. 

The Kylie Cosmetics owner is "very torn on how to handle the situation," but ultimately, the source said, Kylie, along with the rest of her family, are "writing Jordyn off."

Kylie Jenner and Jordyn Woods' Friendship Through the Years

But Jordyn, 21, isn't just a friend to Kylie, she's family, with a source going so far as to say she's "another sister," with the two women even living together in Kylie's home. 

She's also been one of the family's most trusted inner circle members, invited to events such as Kim Kardashian and Kanye West's 2014 wedding and Khloe's baby shower, and even defended Khloe and Tristan's relationship after his first cheating scandal.

"I think they just have fun together," Jordyn said of the Cleveland Cavaliers player and Khloe in September 2018. "I feel like they have great chemistry, so that works out well."

Now, after reports surfaced that Tristan, 27, and Jordyn hooked up at a house party, where a source told us people could tell "they were into each other," the model and clothing designer has been silent on social media.


Kylie and Jordan met when they were in eighth grade through mutual friend Jaden Smith.

"One day I got a phone call from one of my friends and they were like, 'Yeah, come over to Kylie's house. We all wanna hang out,'" Jordyn explained in a Buzzfeed interview. 

Kylie continued telling their middle school meet-cute, saying, "And she put her name in my phone and we just got closer and closer throughout the years and realized all we need is each other. Now we are our only friends!"

And while Kylie was a main cast member on one of TV's most popular reality shows from the age of 10, the duo acted just like any other teenagers would.

"We used to Segway everywhere. I mean everywhere when we didn't have our license. Like we would Segway outside the community to like, miles and miles to the mall," Kylie revealed. 

A History of Khloe Kardashian and Tristan Thompson's Relationship

Viewers got a front row seat to the deep connection between the BFFS during E!'s Life of Kylie, which ran from August through September 2017 and documented the private life of one of the world's most famous teenagers.

After her solo spinoff was announced, Kylie said in a statement, "The last couple years have been such an incredible journey with the support of my fans," also adding, "This show will allow me to give them a peek inside all of the exciting things I am working on as well as some personal time with friends."


But really, the show was just as much about Jordyn as it was Kylie, with cameras documenting the young model coping with the devastating death of her father, as well as trying to establish her own identity and professional life outside of her friendship with Kylie. 

"I didn't want to do the show at first. But Kylie and I are a big part of each other's lives, so if it's about her life, I'm a key player, so I'm not gonna just not come around," she told Refinery29 in an interview. "I figured, being with her all the time is already my life, so we might as well do it. And it turned out to be really fun, we're just super silly on the show."

Super silly but also super sincere in their love for each other, supporting each other through their most difficult experiences, like Jordyn losing her father, John Woods, to cancer in January 2017. John was a sound engineer on The Fresh Prince of Bel-Air for its entire series run, becoming very close pals with Will Smith. This friendship led to their families becoming close, like Jaden and Jordyn.

"My Fire Ox, My Brother, My Soul Sister. Give Jordy & her family some support and prayers right now," Kylie posted on Instagram after his passing. "I love you the long way @jordynwoods. The other half of me … When you cry I cry."

She also donated $10,000 to a GoFundMe page to help the Woods family raise funds for the memorial service and John Woods' medical bills.

In Life of Kylie's finale, the friends even had a commitment ceremony while they were in Peru for so they could reaffirm their friendship, with Kylie explaining, "I want people to know that we're more than that. She's my girlfriend. I care for her like I care for my girlfriend."

And during the ceremony, she told Jordyn, "I vow to love you through all our adventures and I vow to take you as my best friend...I promise to encourage you, inspire you, love you, through all the good and bad times."

In return, Jordyn vowed "to always be there for you, through thick and thin. In this life and after." 


The ceremony may or may not have been a legally binding one, but the sentiment was clear: Jordyn is a part of any relationship Kylie has with a guy.

"I feel like I'm extended leg of their relationship, whoever she's with," Jordyn told Buzzfeed, with Kylie quickly adding, "She's like the third wheel." 

Of course, that includes Travis Scott, with the rapper even attending a birthday celebration for Jordyn's mom, Elizabeth Woods, last April. Oh, and the "JW" diamond ring Kylie debuted on Snapchat last March?

"Jacques Webster & Jordyn Woods. Real Ones, Ok..," she wrote. (Jacques Webster is Travis' real name.)

For Jordyn, dating has always been a bit more challenging, with Kylie even trying to play matchmaker for her in an episode of Life of Kylie

"I'm always worried about people's intentions," she admitted to Refinery29. But not too much, because I feel like I can tell instantly if someone is weird or not. Especially with dating guys, I know so many of them want to be able to be like, 'Oh, I'm talking to Kylie's friend, or I just want to be in the friend group,' or it's someone who wants to lowkey be famous or do music, so they just start talking to me to see what they can get out of it. That's how most people are, so I'll try to feel anyone out for awhile before I start trusting them."

Khloe Kardashian's Quotes on Motherhood

And Jordyn was clear she had no interest in dating or maintaining friendships just for the sake of likes on Instagram. 

"A lot of people are just friends for the 'gram. Like, ‘We're both bloggers, so let's hang out and pretend to be cool and take photos the whole time and blog each other,'" she explained. "I'm very much the opposite; I hang out with someone because I'm enjoying myself."

Ditto for Kylie. 


"I think Kylie and I have continued to have a good relationship because we think so much alike. I was actually just talking to her last night about how I realized that not everyone thinks like me," Jordyn shared. "Sometimes you forget, like, you get upset and wonder why someone reacted the way they did, and it's like well, this person wasn't raised like you, or maybe they didn't get a lot of affection growing up, and parenting plays a big role, where they grew up, their morals, how they look at life. No one thinks exactly like you. But Kylie and I are both very logical and we just have a connection. Not everyone is going to get you, so when you find someone who does, you have to hold on to that."

However, in interviews, it was clear Jordyn was frustrated with the assumption that she was just Kylie's BFF without her own life, personality or ambitions. 

"I get comments every day that are like, 'What does Jordyn Woods even do?' They see the cool stuff, but they don't know how hard I work," she told Refinery29. "They don't know that I often book gigs that don't pay, or that I sleep in the tiniest hotel rooms, or that sometimes I get absolutely no sleep. I'm not a complainer, because it's all worth it, but I work hard. I understand that you can't just start at the top. I don't think that I'm famous, and I'm not trying to be. I want to be successful. You can have millions of people following you; that's not success, that's fame. But success pays your bills, success means you're comfortable, that you're happy. That's success to me."

Keeping Up With Jordyn Woods

In an earlier teaser for Life of Kylie, Jordyn said their friendship could sometimes be "draining," explaining, "I actually feel like I'm in a full relationship with Kylie. There are different types of relationships—we're definitely in one. Not necessarily sexual, but definitely emotional. It's draining sometimes. I don't want to say she's a needy girlfriend but..."

And yes, she did admit to getting tired to people only wanting to ask her about Kylie. 

It's not that I don't love Kylie to death, but it's just like, if you want to know about Kylie, you should just interview her," she said, ironically, in her Refinery29 interview. "If you're just going to ask me questions about her, why don't you just talk to her yourself? I have so many things that I'm doing that I would love to share. If I'm promoting something, I'm not there to talk about anyone else other than myself and what I'm doing. I understand why people ask about her, because she is very popular and people want to know about her. And I love it. But I've got to focus on me, too."

Jordyn Woods/Instagram

Attempting to balance her own life with her friendship with Kylie was a struggle viewers watched Jordyn go through in Life of Kylie's eight-episode run, with the BFFs sometimes clashing over Jordyn not coming to all of Kylie's events or skipping potential work opportunities to travel with Kylie, who defended herself by saying, "I've always been a stan for you. Don't make me seem like I'm forcing you to do s—t."

Jordyn admitted, "It's just hard for me to find a balance in my life...I need to just be the best me I can be and you help me become the best me I can be."

Since the show ended, a lot has changed, most notably Kylie becoming a mother for the first time.

Kylie, of course, gave birth to Stormi Webster in February 2017, and while she chose not to publicly confirm her pregnancy, a small, tight-knit group of family and friends, including Woods, were part of her support system. In the 11-minute video Kylie released after announcing Stormi's pregnancy, titled "To Our Daughter," Jordyn, who was filmed attending some of her friend's doctor's appointments with her, spoke to Kylie's baby, saying, "When you're 20-years-old, you're just figuring out your life. You don't know what you want. You're an indecisive teenager, and you're just becoming a young adult, and there was one thing that your mom knew for sure, and that was you."

Stormi Webster's Cutest Photos

And after Stormi's arrival, the BFFs' already tight bond has only gotten stronger. 

"I think it just has gotten better," she told E! News in August 2018. "It is a part of life and the process of growing up. I think it has been really great with her around now. Stormi is so sweet and so beautiful. I love hanging out with her all day."

When Kylie celebrated Stormi's first birthday with a beach vacation, it was Jordyn by her side for the milestone.

On Instagram, Jordyn model wished Stormi a happy birthday birthday .

"You never fail to make me happy. You are the sunshine on any day and there is never a dull moment with you," she wrote. "I can't wait to continue to see the smartest little girl I know blossom and grow. Your Aunty Jordy loves you baby. HAPPY 1st BIRTHDAY ROCKSTAR. and when I say rockstar.. I mean it. This girl has rhythm already."

While the BFFs often play together, including Kylie hosting two lavish 21st birthday celebrations (one in LA and one in Miami) for Jordyn, they recently started working together too, with the pair officially teaming up for Kylie's Jordyn Woods x Kylie Cosmetics makeup collaboration back in September. 

"i wanted to come on here and let you know just how special this collection really is to me. jordyn and i have had a true unmatchable relationship and i consider her family," Kylie wrote on Instagram when announcing the special collection. "she's helped me remain ME throughout all these years and this is the first time we have collaborated on such a project! it has been so much fun and I'll cherish the memories forever!"

In her own post about the collab, Jordyn wrote to Kylie, "Thank you being the most supportive friend and life partner!" 

The collection featured an eye shadow palette, lip glosses, lipstick and a highlighter palette that all celebrated Kylie and Jordan's friendship, with hues names such as Wife Life, Loyal, Soul Mate, Ride or Die, Don't Ever Leave Me, Partner in Crime, Love You B*tch,  No New Friends, Inseparable, Sister and Together Forever. 

Their makeup team-up was a long time coming, as Kylie revealed Jordyn is actually her test model for all her products in a video for Vogue

"I test out most of my stuff on Jordyn because we live together, So I'm like, 'Jordyn, I need you.' Everyone that comes in my house has tinted red arms from swatches and shadows." 

In addition to the successful Kylie Cosmetics line launch, Jordyn has been busy establishing her own empire, creating a fashion brand.

Jordyn launched SECNDNTURE, a size-inclusive activewear brand, in August 2018, and her mogul BFF offered some marketing advice when it came to dropping the news on Instagram. 

Kylie Jenner's Best Looks

"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?'" she told Fashionista. "I was like, 'Calm down, I'll do it.'"

The clothing line came after Jordyn developed a passion for working out following the devastating loss of her father. 

"My workouts have inspired me to make an activewear line because it's so difficult to find supportive clothing and clothing that's cute and actually inspires you to get up," Jordyn told E! News


After losing weight due to her newfound love of fitness, Jordyn received some criticism from her followers 

"I did get some people saying that, 'Oh you're not a body positive person anymore.' [But] body positivity to me is loving yourself and wanting to be the best version of yourself and not caring what anyone has to say," she told Teen Vogue

She added, "Everyone always has something to say. Everyone has an opinion and as long as you're happy in who you are and what you're doing, that's all that matters."

I's also "helpful" to have someone going through a lot of the same things as you are, especially in the public eye, something Kylie knows a thing or two about considering it often feels like her every meal, move and Snapchat is documented and commented on. 

"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," Jordyn told reporters in 2017. "Honestly, you can't really trust anyone. You really can't. People stab you in the back all the time, but I feel like my friendships that I have, you just have the same understanding."

She continued, "Having a best friend is, like, everything. I feel like everyone deserves a best friend. It's just like having someone you can call at any time. Obviously, I have my family and I have my mom, but sometimes you need that extra person that isn't a part of everything, going through the same things as you."

For Jordyn, that person has been Kylie for almost a decade.


But when she was also asked believed her friendship with Kylie would last forever, Jordyn had a somewhat cryptic response.

"Nothing's forever, but for as long as I can imagine, I believe so."

Now? Everything has changed in the wake of the Tristan scandal, as a source told E! News Kylie is "devastated" over the allegations as she considers Jordyn a "sister."  

"Kylie is having a very difficult time. She is devastated and emotional. She doesn't want to believe this could have happened," our insider said. "She wanted to give Jordyn a chance to explain herself. 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."

From Day 1

"Get you a best friend that looks at you like this," Jordyn wrote alongside this Kodak moment between her and Kylie.

Daring in Denim

The duo sits front row during Jonathan Simkhai's New York Fashion Week runway show in 2016. 

Always & Forever

"Twin Souls," the model shared on social media in 2016.


Jordyn and Kylie snap a selfie a few years back, writing on social media at the time, "When bae surprises you on set."

Inseparable Duo

Kylie and Jordyn look stylish as they hit the party circuit during NYFW 2016. 

Three Amigas

"They're sisters at this point," Jordyn captioned this photo of her, Kylie and Anastasia Karanikolaou.

Flaunt What You Got

Hot Mamas! Kylie and Jordyn pause for an impromptu photo shoot in a pair of equally as daring bikinis. 

Mad Love

"Reposting because whether we like it or not we're stuck together forever," Jordyn captioned this snapshot of the pair in 2017.

Another Day, Another Selfie

The girls collab on additions to Kylie's merch line in 2017.


The besties that travel together, stay together! Kylie and Jordyn are pictured here attending Louis Vuitton's Paris Fashion Week show in 2018. 

Prom Queens

The E! reality star and model board a private jet in 2017 to surprise a lucky fan before his high school prom. 


Kylie and Jordyn coordinate their sporty chic ensembles while arriving arm-in-arm to Tristan Thompson's 27th birthday party in March 2018.

Supporting Each Other's Dreams

Kylie supports her BFF at the launch event of her activewear line, SECNDNTURE, in 2018. 

Good Ol' Days

"We've traveled lives together," the cosmetics mogul gushed on Instagram in 2018. 

Hip Hip Hooray

The gal pals are inseparable as they arrive to Jordyn's 21st birthday bash in West Hollywood in Sep. 2018. 

Out on the Town

Kylie and Jordyn ring in 2019 by each other's side.

Time to Get Away

The besties enjoy a tropical vacation with Kylie's little girl, Stormi Webster, in anticipation of her 1st birthday in Feb. 2019.