Saionji's relationship with Utena is probably the most clear-cut out of all the female characters in the anime. Simply put, Utena is the person Saionji has always wanted to be. Rebellious, popular, and strong, Utena has a power of vision that Saionji most definitely envies. Utena is able to stand on her own against Touga, something Saionji has longed to do but doesn't have the willpower to.

Utena's victory over Saionji is a stunning blow to him. Besides Touga, no one has ever bested Saionji in a duel, and the fact that Utena, a newcomer to the school and the duels, has done so, vastly undermines Saionji's position of power. Here we see Saionji struggling to hold on to the prestige he has earned, while a young and unknown duellist steals both Anthy and his reputation from under his nose.

The Saionji/Utena relationship, therefore, can be classified as one of pride and jealousy. Saionji's pride of underestimating Utena is his downfall. Utena's simple, straightforward, and truthful viewpoint on life, combined with her belief in dreams, is a source of jealousy for the man who long ago stopped believing in eternity.