>>90522158this is more than just one girl vs the other.
Star represents escapism and childlike, somewhat feminine, fantasies. Fantasies of a young man who was brought up in modern feminist society and thus, has a very feminine inner desire to get saved by a hero and then have hot sex with them, which in this case is an inverse of the classical "damsel in distress" situation. If he chooses Star, that means he distances himself from reality and dwells into the world of his dreams.
Jackie represents reality, a girl that's perfectly fitting for a masculine, alpha male. She has all the stereotypical classical traits of an attractive female, and only a true alpha male could have the power to control her. Young man presented in the series, still being a man, has the potential to become one, but for that, he has to decide what really matters to him in life. If he chooses Jackie, that means he "grows up" and ignores his inner fantasies in order of successful personal life in reality.
This is truly the level of depth unseen before in Disney animated shows.