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Jaden Smith didn’t choose sides for his longtime friends, Kylie Jenner and Jordyn Woods

In February 2019, Jenner and Woods’ friendship took a turn for the worse. She and Tristan Thompson reportedly shared a kiss at an LA party. The NBA player was dating Khloé Kardashian, and the two share a daughter- True Thompson, 2. After the backlash from the night’s events, Woods lost communication with the family, and she and Jenner have yet to rekindle their relationship. 

 Kylie Jenner attends the 2020 Vanity Fair Oscar Party at Wallis Annenberg Center for the Performing Arts on February 09, 2020 in Beverly Hills, California./Actor / Rapper Jaden Smith attends the "BET Twenties" produced by Lena Waithe Screening during the Sundance Film Festival on January 27, 2020 at Park City Live in Park City, Utah. /Jordyn Woods attends BET+ And Footage Film's "Sacrifice" Premiere Event at Landmark Theatre on December 11, 2019 in Los Angeles, California.
(L-R) Kylie Jenner, Jaden Smith and Jordyn Woods| Toni Anne Barson/WireImage, Aaron J. Thornton/Getty Images for BET, Leon Bennett/Getty Images for BET

At the height of the scandal, Jada Pinkett Smith was one celebrity who Woods confided in. However, many fans wondered why Jaden didn’t play more of an integral role in the matter, as he grew up with them both. 

Jaden Smith reportedly wanted to ‘stay neutral’ when the Kylie Jenner and Jordyn Woods feud began

When news broke out that Woods and Thompson had allegedly had an affair while he was still with Kardashian, the model became the subject of public fodder. Woods shared that she felt isolated during that time and that she had lost the life she became accustomed to while with Jenner and her family. According to Hollywood Life, the Smith family took Woods in and gave her a chance to tell her truth. In March 2019, Woods sat down with Pinkett Smith to apologize to Kardashian and explain her role in the scandal.

While Pinkett Smith was all on board to help Woods, Smith supported Woods and Jenner separately. Since he didn’t attend the house party where Woods and Thompson allegedly kissed, he reportedly had nothing to say.  

“[Jaden is] the kind of guy who strays away from drama and since this has nothing to do with him, he’s staying out of it,” an insider shared. “Jada is also the kind of mom who encourages her kids to stay neutral in these kinds of situations, too, so even though the family as a whole are friends with the Woods’, she wouldn’t ask her kids ever to pick a side.”

Jaden Smith’s relationship with Jordyn Woods

Smith’s friendship with Woods dates back to the early stages of their childhood. The two met through their fathers, as Woods’ dad, John, was a  TV sound engineer on The Fresh Prince of Bel-Air, and became friends with Will Smith. Woods and her family soon moved to Calabasas, and she and Jaden formed a tight bond shortly after. 

Woods has referred to Smith as her “brother for life” in a touching Instagram post for Smith’s 22nd birthday.  In 2015, Smith also gushed about his friendship with Woods and shed more light on their relationship. 

“Jordyn Is One Of The First People I Ever Met, We’ve Been Friends Since A Few Days After I Was Born And Always Will Be,” Smith wrote on Woods’ Instagram page in October 2015. Lexington Lives Through The Spirit Of Sherman Way. Remember This.” 

Jaden Smith’s relationship with Kylie Jenner

Although he’s known Woods longer than Jenner, Smith and the Kylie Cosmetics founder once shared a unique connection. According to E! News, the friends met through Woods when they attended middle school together. Soon after their initial meeting, Smith, Jenner, and Woods hung out on multiple occasions and shared some of their social media musings.

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Several rumors surfaced that Smith and Jenner dated in high school, which is something both of them have denied. In terms of loyalty, though, Smith reportedly wanted Jenner and Woods to mend fences so the friendship could get back on track. If things went further south, though, Smith’s allegiance would have reportedly been with Jenner and her family. 

“Jaden would love to see Kylie and Jordyn fix this, but he’s made it clear he’s not getting involved at all,” an insider said. “Jaden is definitely staying out of it as much as possible and hopefully completely, but if he were ever forced to pick a side the Kardashians would win his loyalty.”