The Untold Story Behind Kylie Jenner and Jordyn Woods' Complex Friendship Journey

Jordyn Woods, Kylie Jenner. Broadimage/Shutterstock

Kylie Jenner and Jordyn Woods recently reunited, but their renewed friendship is still a work in progress.

According to a source exclusively speaking to We, it was Kylie who reached out to Jordyn. She had missed her and felt that enough time had passed, so they decided to meet up.

Jenner and Woods, who are both 25 years old, were seen having dinner together in Los Angeles on Saturday, July 15. This is the first time in four years that the pair has been seen together in public. According to a second source, their relationship is a work in progress and they are taking things slowly.

Jenner's friendship with Woods may have been facilitated by Khloé Kardashian. According to the first source, the Kylie Cosmetics founder obtained "permission" from her 39-year-old sister to reconnect with Woods.

The insider clarifies that Khloé, who emphasizes forgiveness and progress, is accepting of Kylie spending time with Jordyn.

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Following years of inseparable companionship, Jenner and Woods' relationship took a bitter turn in February 2019 when Woods was caught kissing Kardashian's former partner, Tristan Thompson.

The Jenner-Kardashian family was shaken by the cheating scandal, leading to the separation of the Good American cofounder from Thompson, 32. As Kardashian tried to rebuild her personal life, Jenner distanced herself from Woods. (Thompson has faced previous accusations of cheating on Kardashian with multiple women while she was pregnant with their daughter, True, who was born in April 2018.)

During a March 2019 interview on Red Table Talk, Woods claimed that she apologized to Khloé as much as she could, both over the phone and through text. She maintained that the kiss with Thompson had no emotional attachment at the time.

In August 2020, Us broke the news that Kardashian and Thompson were rekindling their romance. However, they officially ended their relationship in 2021 due to Thompson's paternity scandal with Maralee Nichols. Thompson confirmed in January 2022 that he is the father of Nichols' son, Theo, who is now 19 months old, despite being in a relationship with Kardashian at the time.

Meanwhile, Thompson and Kardashian have two children together: True, who is 5 years old, and a son who they welcomed via surrogate last summer. Thompson also has a son named Prince, who is 6 years old, from his previous relationship with Jordan Craig.

Kardashian, on her part, appeared to handle the situation gracefully this month when Jenner and Woods’ dinner date garnered attention. On Sunday, July 16, she shared an inspiring quote on her Instagram Story that read, "Never blame anyone in your life. The good people give you happiness. The bad people give you experience. The worst people give you a lesson. The best people give you memories."

In another quote, Kardashian encouraged her followers to choose kindness, stating, "It's easy to judge. It's more difficult to understand... Through judging, we separate. Through understanding, we grow."