Played By: Alexis Bledel and Matt Czuchry 

Before Yale, Rory was the quirky girl next door with her heart torn between the tall, dark and handsome Dean and the broken bad boy, Jess, which made for an entertaining love triangle to watch. During Yale, the aspiring reporter lost that spark and instead got involved with a smug, incredibly vanilla newspaper magnate's son whose chemistry with her wasn't quite the His Girl Friday-type producers were going for.