In the Pilot , Dean Forester is introduced as the new guy in town. He has a younger sister named Clara. He quickly falls for Rory, and becomes her first real boyfriend. He breaks up with her in season 1 when he tells her that he loves her and Rory doesn't say it back, but they get back together in the season finale.Throughout seasons 2 and 3, ...
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In the Pilot , Dean Forester is introduced as the new guy in town. He has a younger sister named Clara. He quickly falls for Rory, and becomes her first real boyfriend. He breaks up with her in season 1 when he tells her that he loves her and Rory doesn't say it back, but they get back together in the season finale.Throughout seasons 2 and 3, their relationship becomes strained, especially once it become clear that Rory has feelings for Jess Mariano. Dean breaks up with her for the second time during a dance marathon, when Rory's feelings for Jess become painfully obvious. Later, he and Rory become friends again.Dean eventually begins to date a girl named Lindsay,and they get married. The night before the wedding, Dean gets drunk and talks about Rory, showing that he still isn't over her. His marriage to Lindsay is short-lived, ending when he and Rory have an affair. Lindsay finds out about it upon discovering a letter that Rory had written to Dean while she was in Europe over the summer.Dean and Rory date for a short time at the beginning of season 5, but he breaks up with her for the final time when he was going to pick her up at her grandmother's house, and realizes that he no longer fits in with Rory's new lifestyle.In To Live And Let Diorama , Dean talks to Luke, telling him that his relationship with Lorelai is just like his relationship was with Rory. Dean says that Luke cannot give Lorelai the life she wants, and that eventually she is going to get bored and leave him.Dean is never seen or heard from again for the rest of the series.
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