Rory Gilmore and Jess Mariano’s relationship throughout Gilmore Girls and its revival, A Year in the Life, remains one of the most talked-about and divisive storylines. From their rocky beginnings in Stars Hollow to their more mature interactions years later, Jess stands out as a character who challenged Rory in ways few others did. Many fans appreciate Gilmore Girls’ Jess for encouraging Rory’s schooling and understanding of her personality, often viewing him as a better intellectual and emotional match than her other partners.