In high school, Jenner dated fellow classmate and high school football star Julian Brooks. While their relationship fizzled out in 2013, they had their share of memorable moments.
"When I got to high school I used to pretend that I had work, and I would go and tell the head of school that I really needed to leave and that I was really stressed out because I had work," Kendall told Hello!. "But then I would just leave school — and I would bring [sister] Kylie [Jenner] with me, but she didn't get permission. I would just leave school and go hang out with my boyfriend and get food and do absolutely nothing."