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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.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.
Earlier in the season, Jess had taken a job at Walmart, and he continuously missed school to work extra hours.When he kisses her back, she pulls away and starts freaking out resulting in her running away screaming "welcome home". Rory returns, and Jess expresses his anger over her still being with Dean and not communicating with him while she was away, especially after kissing him months earlier.Rory stays with Dean after resolving that being with him is the better choice, but she continues to show her attraction and interest in Jess.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.Jess gets angry and yells at her for bothering him.