Dean sherman and dating
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Jess quickly develops a romantic interest in Rory Gilmore after he meets her at a welcome to town dinner at her and her mother's house.Jess eventually agrees that he was right, and they begin their relationship.Their relationship, however anticipated by each other, is bumpy.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.
Because of this, Jess later returns to Stars Hollow with the intention of doing better than the first time he was there.