Dean Forester
Wikipedia
Gilmore Girls Character Guide
Dean Forester was a main character in season 2 and 3, while he was a recurring guest star in seasons 1, 4, and 5. He is introduced as the new guy in town in the "Pilot". He entered into a relationship with Rory Gilmore after she shows him around Stars Hollow. Rory in turn quickly becomes infatuated with him, and he becomes the first serious boyfriend for Rory. Later, however, Jess Mariano is introduced. Although the couple were 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. Although his attraction to Rory remains so strong that, at a party, when he discovers that Jess made her cry, he violently attacks Jess, resulting in a brawl between the two. Dean and Rory do not rekindle their relationship as Dean remains with Lindsay and soon impulsively marries her. However, it is still obvious that he carries strong feelings for Rory. On the night before his wedding to Lindsay, Dean expresses to Luke that he feels Rory is the only girl he can marry, later forgetting the statement. 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.
Lorelai accidentally finds out about the affair and becomes angry with their actions, saying she did not raise Rory to have an affair with a married man, which briefly complicates things with Rory. Dean and Lindsay's relationship is later ended, Lindsay having found out about their affair. Although it seems unclear if Rory and Dean will get back together, he decides to rekindle his romance with Rory. This aggravates many people in their lives including Luke and Rory's grandparents and Dean's parents. To make matters worse, Dean and Rory find their lives heading in completely different directions. With Rory rarely in Stars Hollow due to her life at Yale and Dean holding three jobs at once to make ends meet, the two of them rarely find time to spend together; both cancel date after date due to their commitments and somewhat problematic living situations.
The two finally find time for a date; it would be planned that Dean would pick Rory up after a party that her grandparents planned to throw for her. However, the party was thrown with the sole purpose of introducing Rory to other prospective blue blooded boyfriends with business aspirations, including Rory's next boyfriend, Logan Huntzberger. Rory enjoys herself at the party so much that she briefly forgets about her planned outing. She eventually remembers, and by the time she walks out to a furious Dean, the two realize that their lives were heading in different directions, and Dean ends their relationship for good.
In his final appearance in "To Live And Let Diorama", Dean does not see Rory, but rather Luke. Dean relates his faulty relationship with Rory to Luke's relationship with Lorelai, saying that ultimately, Luke would hold Lorelai back from whatever potential she may have. With this statement, Dean is never seen or heard from again.
In the revival, he runs into Rory in Doose's market. He's visiting his parents, but he lives in Scranton with his second wife and kids. Rory tells him she is thankful for their relationship and how he taught her what safe feels like. They part amicably.
Dean later starts dating a girl named Lindsay Lister. Although his attraction to Rory remains so strong that, at a party, when he discovers that Jess made her cry, he violently attacks Jess, resulting in a brawl between the two. Dean and Rory do not rekindle their relationship as Dean remains with Lindsay and soon impulsively marries her. However, it is still obvious that he carries strong feelings for Rory. On the night before his wedding to Lindsay, Dean expresses to Luke that he feels Rory is the only girl he can marry, later forgetting the statement. 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.
Lorelai accidentally finds out about the affair and becomes angry with their actions, saying she did not raise Rory to have an affair with a married man, which briefly complicates things with Rory. Dean and Lindsay's relationship is later ended, Lindsay having found out about their affair. Although it seems unclear if Rory and Dean will get back together, he decides to rekindle his romance with Rory. This aggravates many people in their lives including Luke and Rory's grandparents and Dean's parents. To make matters worse, Dean and Rory find their lives heading in completely different directions. With Rory rarely in Stars Hollow due to her life at Yale and Dean holding three jobs at once to make ends meet, the two of them rarely find time to spend together; both cancel date after date due to their commitments and somewhat problematic living situations.
The two finally find time for a date; it would be planned that Dean would pick Rory up after a party that her grandparents planned to throw for her. However, the party was thrown with the sole purpose of introducing Rory to other prospective blue blooded boyfriends with business aspirations, including Rory's next boyfriend, Logan Huntzberger. Rory enjoys herself at the party so much that she briefly forgets about her planned outing. She eventually remembers, and by the time she walks out to a furious Dean, the two realize that their lives were heading in different directions, and Dean ends their relationship for good.
In his final appearance in "To Live And Let Diorama", Dean does not see Rory, but rather Luke. Dean relates his faulty relationship with Rory to Luke's relationship with Lorelai, saying that ultimately, Luke would hold Lorelai back from whatever potential she may have. With this statement, Dean is never seen or heard from again.
In the revival, he runs into Rory in Doose's market. He's visiting his parents, but he lives in Scranton with his second wife and kids. Rory tells him she is thankful for their relationship and how he taught her what safe feels like. They part amicably.