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Dean Forester, portrayed by Jared Padalecki, is a main character in seasons 1 through 3 of Gilmore Girls, and recurring afterward. He is first introduced as the new guy in town in the Pilot. He immediately falls for the shy, sensitive intellect, Rory Gilmore (Alexis Bledel) after she shows him around Stars Hollow. Rory in turn quickly becomes infatuated with him, and he becomes her first serious boyfriend.

Is season three Luke's nephew, Jess Mariano (Milo Ventimiglia), moves to Stars Hollow. Dean takes an instant dislike to him due to Rory's growing interest in him. Although the couple was having problems before Jess, their relationship is further strained after Rory spends more time with Jess. Dean is eventually driven to jealousy by Jess' presence and this leads to the end of his relationship with Rory.

Dean later starts dating a girl named Lindsay Lister (Arielle Kebbel) and impulsively marries her. However, it is still obvious that he still carries strong feeling for Rory. Dean remains too close to Rory and, when it becomes clear to him that he's made a mistake in marrying Lindsay, he goes to Rory and starts an affair- Rory's first sexual experience. When Lindsay eventually finds out, she throws out Dean. But Dean decides to rekindle his romance with Rory.

They soon realize that their lives were heading in different directions, and Dean ends their relationship for good. In his final appearance, Dean does not see Rory, but rather Luke. Dean relates his faulty relationship with Rory to Luke's with Lorelai, saying that ultimately, Luke would hold Lorelai back from whatever potential she may have. With this statement, Dean is never heard from again.