Milo and alexis dating
Rory would like to attend her senior prom at Stars Hollow High with Jess, but when he tries to get tickets, the principals officially informs him that he will not be graduating (and therefore cannot buy tickets).
Earlier in the season, Jess had taken a job at Walmart, and he continuously missed school to work extra hours.
He also continues to keep secrets from her, like how many hours he's really working at Walmart instead of attending school.
When Rory is accepted to Yale University, Jess seems excited about the close proximity so they can continue their relationship even with her being at school.
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 tends to distance himself from people, leading to his breakup with Rory.
Despite people reaching out to him, he often pushes them away without explanation.
Also, Jess is jealous of the formed friendship between Rory and Dean, and it doesn't help that Lorelai still doesn't warm to him.
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 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 comes to Stars Hollow when his mother, Liz, is frustrated with his attitude and bad behavior so she sends him to live with her brother, Luke Danes.Early on, Luke states that in order for Jess to live with him, he must attend school and graduate.Later in the evening, Rory finds Jess sulking in a bedroom upstairs, and she tries to talk to him.