Jess gets angry and yells at her for bothering him.When she walks downstairs crying, Dean sees her and initiates a fight with Jess.When they meet, Rory is involved with Dean Forester, a local boy she has been dating for two years.

Jess attends the 24 Hour Dance Marathon with his new girl, and after Rory demonstrates clear jealousy over him, Dean breaks up with her publicly at the school dance as he's tired of being dragged along when the two clearly have feelings for each other.

Jess finds Rory sitting on the deck at the lake afterward, and she confesses that everything Dean said about them was right.

Jess shows his interest in Rory in several situations, but after a tutoring sessions ends in a car accident with Rory in the hospital, Luke puts Jess on the bus back to his mother.

Rory unusually skips school for the day and unexpectedly misses her mother's graduation to take a trip to New York to see him, and when he asks her why she came, she says he never said goodbye.

Jess arrives late to a dinner at Rory's grandmother's house where he shows up with a black-eye and later walks out on the evening after he and Rory get into an argument.

He later reveals he was attacked by a swan and takes Luke to the pond to retaliate with a ladle.

This causes the tension between Jess and Rory to skyrocket, and he walks away from the party without looking back.

When Luke finds out that Jess refuses to repeat his senior year, he and Jess get into an argument.

Jess is incredibly smart, quick-witted, and interested in the arts and literature, but not academically motivated.

His lack of parental support from his mother and the absence of his father leaves Jess feeling very alone and scared of the world, which causes him to test or lash out at most people.

Jess also works part-time in the diner his uncle owns.