Before Jacks parents died, Jack and Vanessa dated during highschool. At the time, Jack hadn't begun transitioning making the relationship Vanessas first with another "girl". Jack was naturally uncomfortable with physical affection and he struggled to open up emotionally while Vanessa expressed love through constant touch, hugs and open displays of affection.
After Jacks parents died everything just got worse regarding their relationship. His grief made him withdraw even further. Communication between Jack and Vanessa became increasingly strained and eventually Jack dropped out of high school altogether effectively ending the relationship without much closure. I don't think they would've officially broke up because Jack would've slowly started to come in less and less.
Vanessa stayed in highschool and stayed on the cheer squad. She was extremely energetic and enthusiastic but also incredibly clumsy (which is why she has so many bandages).
