Kylie Jenner and Jordyn Woods' Friendship Timeline: From Their First Meeting to Cheating Scandal and Reunions

Kylie Jenner and Jordyn Woods proved friendships could have happy endings, too.

The Keeping Up With the Kardashians alum had been friends with Jaden Smith since middle school. Jenner met Woods for the first time when she and Smith invited her over to hang out before they started high school.

Woods joined the Kardashian-Jenner clan's Christmas party in December 2013. Following the holiday event, she uploaded her first photo with Jenner on Instagram.

"Merry Christmas from the goths❤️," the "Be With You" songstress captioned the post.

As they developed a deeper connection, the duo decided to get matching tattoos on their inner pinkies, inked by celebrity tattoo artist JonBoy.

Jenner's Life of Kylie, a spinoff of KUWTK, premiered in 2017, exploring the day-to-day life of the Kylie Cosmetics founder. The two-part season also featured Woods.

Jenner and Woods held a "marriage for friends" in a traditional commitment ceremony on the Life of Kylie season finale.

"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," Jenner said of Woods. "All I want for Jordyn is to have all the success in the world and I want her to know that I'm always gonna be here to support her on whatever. I just think everything is happening perfectly for her. She's going at the perfect pace."

She also expressed how "proud" she was of Woods and the things she had accomplished so far, calling her pal "my ride or die."

"Vice versa. We might not always be together, but we will always be connected in the mountains of Peru," Jenner continued.

Following the extravagant birthday celebration Jenner threw for Woods, the SECNDNTURE founder spoke highly of their friendship during a charity event on World Smile Day.

"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," Woods said. "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. It's really helpful."

The model added, "I feel like right now, at this age, you develop the friends that you're going to have forever, and we do everything together."

When asked whether she thought their friendship would endure everything, Woods noted, "Nothing's forever, but for as long as I can imagine, I believe so."

While filming a makeup tutorial for Vogue, Jenner revealed she and Woods were staying under the same roof.

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

Their years-long friendship was tested in 2019 when multiple news outlets reported that Khloé Kardashian and Tristan Thompson called it quits after the Canadian basketball player cheated on her with Jenner's best friend.

"Khloé loved Jordyn before this," a source said after the bombshell revelation. "This is completely shocking to Khloé's family."

After maintaining her silence, Woods sat down for an interview on Red Table Talk, revealing she realized things went wrong when she stayed at Thompson's house until "6 in the morning."

"And how I would feel if someone close to me is hanging out at my ex's house, or the father of my child? I didn't think about that," she admitted.

Woods also confirmed Thompson kissed her but noted she had "allowed [herself] to be in that position."

She continued, "And when alcohol is involved people make dumb moves, or people get caught up in the moment or who knows."

In an E! News supertease for the 16th season of KUWTK, Kris Jenner told Kylie it was like a "divorce" for her and Jordyn.

"She f----- up," Kylie responded before supporting Khloé. "Just know I love you."

In the months following her Red Table Talk interview, the former The Masked Singer contestant frequently discussed the scandal and its impact on her and Kylie's friendship.

"Jordyn's position now is she's going to just let it be what it is," a Woods family friend told People. "She said what she had to say."

In September 2020, Jordyn disclosed she dealt with shame due to the controversy.

"I remember just sitting in a very dark place," she told Now With Natalie host Natalie Manuel Lee. "I had my family to talk to, I had you to talk to, but I just felt like I had no one."

Jordyn added, "You take everything you think you know for a whole decade, the people you think you know, the life you think you know, everything that you've grown up doing and you take it all away from someone. I didn't even know how to feel."

The Daily Mail released photos of Kylie and Jordyn leaving a Los Angeles restaurant together four years after the scandal emerged.

"Kylie was the one to reach out to Jordyn," an Us Weekly source said of the pair's reunion at the time. "She missed her and felt enough time had passed and they wanted to meet up."

Meanwhile, a separate insider told People that Kylie and Jordyn reconciled before their first public outing.

In a May 2024 episode of The Kardashians, Kylie revealed she met Jordyn again in Paris.

"It was fun. I think we have a lot more healthy distance in the relationship. Now it's like, we talk once a month," said the mom-of-two.

Although things improved after the reunion, the Khy founder looked back on their fallout in an interview with Elle.

"I was heartbroken," the Trolls: Holiday in Harmony voice actress confessed. "We've always tried to talk through things, so it's never been a full cold-turkey cutoff; it was needed distance."

On the other hand, the split also had a positive impact on their friendship.

"Anytime something happened, good or bad, and I needed to call someone, it would always be her," Kylie added. "To lose that person felt really lonely, but I had to go through that."

She shared, "I learned so much, gained so much independence, and was there for myself. It helped me grow up a little bit, because we were so attached at the hip. I think that in order for us both to grow, she needed to spread her wings and do what she needed to do as well."

Kylie and Jordyn had another sweet BFF moment when they reunited courtside at the New York Knicks and Boston Celtics game on May 12.