‘Gilmore Girls’: Dean Forrester’s Downward Spiral Documented

By now, most Gilmore Girl fans agree that Dean Forrester and Rory Gilmore were never meant to be a forever couple. Their incompatibility and young ages meant their relationship would never last, but Dean still had some good qualities. By the time that Dean walked through Stars Hollow for the last time, he was a shadow of his former self. All told, the series creator, Amy Sherman-Palladino, did the character of Dean very dirty. Let’s look at his downward spiral. 

Dean appeared in the pilot episode of Gilmore Girls

Dean was Rory’s very first boyfriend. Initially characterized as the “new kid”, Dean showed an interest in Rory after seeing her around Stars Hollow High School before she transferred to Chilton. He went out of his way to pursue her, and shortly before Thanksgiving, the pair kissed for the first time. Their relationship spanned two years and ended when Rory’s feelings for Jess Mariano became clear. 

Dean’s calm and cool persona was established during the earliest episodes of the series and was maintained for most of his time on the series. Suddenly, though, everything changed. By season 4, Dean was a much different man. Fans still can’t understand why a perfectly nice, if not boring character morphed into someone so unlikeable. 

Dean Forrester’s decline began in season 3  

For season 1 and most of season 2, Dean was “the perfect boyfriend.” He supported Rory, understood her commitment to education, and showed up when Rory needed him to, even if it meant wearing a tuxedo for a debutante ball. As Rory’s feelings for Jess Mariano develop, Dean started to change. He was clingy, combative, and insecure. Fans could mostly forgive those behaviors. After all, he was a young man who realized his girlfriend was losing interest in him. 

Alexis Bledel as Rory Gilmore and Lauren Graham as Lorelai Gilmore pose in Luke's Diner
Rory and Lorelai Gilmore in ‘Gilmore Girls’ | Warner Bros./Delivered by Online USA

RELATED: ‘Gilmore Girls’: Why Did Dean Marry Lindsay in the First Place?

Dean’s real downfall came in season 4 and only got worse in season 5. First, Dean continued to pursue Rory even though he had married Lindsay Lister. After sleeping with Rory, he yelled at his wife. When Lindsay learned about his affair, he attempted to blame Rory for it.

Things didn’t get better when he and Rory finally got back together, either. He failed to show interest in what Rory was doing at school and took out his frustration on her fairly often. Dean went from a mostly sweet, if not immature teen, to an angry, frustrated, and aggressive young man. 

Dean left Gilmore Girls in season 5 in an angry huff 

Reddit users note that by the time fans saw Dean for the last time, he had morphed from a mostly sweet and supportive kid from Chicago to an angry, bitter adult who felt oddly defined by a hamlet he moved to as a teenager. His last appearance did nothing to return Dean to his former self. Rather, it cemented his new persona. 

Dean Forrester and Rory Gilmore run into each other in Doose's Market in 'Gilmore Girls: A Year in the Life'
Dean Forrester and Rory Gilmore in ‘Gilmore Girls: A Year in the Life’ | Netflix

Dean’s last moments in the original series consisted of him telling Luke that Lorelai Gilmore was always going to want more than Luke could offer her, just like Rory would always want more than he could provide. The bitterness was almost painful. By the time fans caught up with Dean in Gilmore Girls: A Year in the Life, things seemed to be better. He had moved away, remarried, and had several children. Still, most viewers can’t shake how Dean changed over time.