Kendall Jenner Admits She Was “Jealous” of Kylie Jenner Growing Up

Published: Oct 31 2025

Kendall Jenner has finally let the cat out of the bag on a long-held family secret. In a candid confession during the October 30 episode of "The Kardashians," the supermodel admitted to feeling "jealous" of her younger sister Kylie Jenner during their childhood, particularly since their parents, Kris Jenner and Caitlyn Jenner, were more lenient on the Kylie Cosmetics mogul.

Recalling their teenage mischief, Kylie revealed that she often smoked weed with friends at their parents' Hidden Hills home, where much of "Keeping Up With the Kardashians" was filmed. "Kylie had smoked weed before me," Kendall shared. "I was so mad at her. I was like, 'You're a degenerate!'" But the 29-year-old explained the source of her anger: "I was jealous. I was jealous that I didn't have as much of a free spirit as her at the time."

Kendall Jenner Admits She Was “Jealous” of Kylie Jenner Growing Up 1

However, Kendall found a way to mend fences. "I eventually smoked with them and then had the best time ever. Everything was great," she said. According to Kendall, they were just 16 and 14 years old when they would sneak out to smoke in the cabana of their backyard.

Kylie managed to skirt many rules as the youngest member of the family, which includes Kris' kids Kourtney Kardashian, Kim Kardashian, Khloe Kardashian, and Rob Kardashian with her late ex-husband Robert Kardashian. "Kris Jenner definitely got more relaxed the more children she had by the time I came around," Kendall explained. "I was definitely afraid of her and respected her, but I could get away with a lot." That's why Kylie said Kendall was "very hard" on her growing up, adding with a laugh, "She was such a hater."

But it's not to say Kendall didn't engage in any mischief herself. After all, the 818 Tequila founder did lose her virginity as a teen. "I lost my virginity in that room," she quipped to Kris while touring her childhood bedroom, before confessing that she actually did it for the first time at her then-partner's house because Kris, now 69, and Caitlyn, 75, "didn't care" about her whereabouts at the time. "Not only did she not know, she really didn't give a f--k," Kendall joked. "She was like, 'Oh, you're going out 'til Wednesday? Great. Never come back.'"

New episodes of "The Kardashians" drop every Thursday on Hulu.

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