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Rory Gilmore’s love life was a point of interest in Gilmore Girls early on in the first season. During the show’s seven-season run, fans watched Rory cycle through three main boyfriends. While they initially loved Dean Forrester, Rory’s high school boyfriend, the shine wore off quickly. Jess Mariano was much beloved, regardless of many of his less-than-ideal qualities, and Logan Huntzberger had a hard time making headway with fans. Still, Dean was probably the mellowest of Rory’s suitors and not all that bad when you think about it.

Dean accepted that Rory and Lorelai were a package deal

Dean might have had some pretty awful qualities. Still, there were plenty of moments where he came through for Rory. When he and Rory first got together, he recognized that Lorelai Gilmore was a part of the package. At 16, he was mature enough to realize that if Lorelai didn’t like him, he didn’t have a shot with Rory, and he managed to win her over. He was polite, helpful, and, overall, pretty understanding.

Sure, Dean had moments of petty jealousy, but he managed to deal with everything the Gilmore girls threw at him with grace and dignity. Fans of the series tend to focus on his moments of anger, but it really did take a lot to upset him when you think about it. His biggest point of contention was Jess. Most people would have reacted to Rory’s growing interest in Jess the same way in the real world.

Dean tried to show an interest in the things Rory liked

Dean and Rory didn’t have a ton in common. She was a prep school student from a rich family, while he had a decidedly middle-class upbringing. Dean didn’t have Ivy League aspirations, while Rory did, and he was way more into athletic pursuits than she was. He also wasn’t a huge fan of reading.

Jared Padalecki as Dean Forrester and Alexis Bledel as Rory Gilmore in 'Gilmore Girls: A Year in the Life'
Dean and Rory in ‘Gilmore Girls: A Year in the Life’ | Netflix

Still, he managed to show an interest in the things Rory liked, and he even sacrificed time he could have spent doing what he wanted to be with Rory. Dean attended the Chilton dance when he didn’t want to. He navigated bookstores and fairs because Rory wanted to go and wore a tuxedo for her. he even put up with Jess scamming on his girlfriend because Rory asked him to be nice to him. Jess certainly wouldn’t have done any of that.

Dean tried to remain friendly, even after Rory humiliated him in front of the whole town

Even after Rory humiliated Dean in front of the entire town by making her interest in Jess obvious, he wanted to remain friendly. Dean went out of his way to be kind and relaxed around Rory. He manages to be kind even while he was still upset about the breakup. Sure, he had a reason for pursuing the friendship. Still, he went out of his way to make Rory feel comfortable.


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Reddit fans do point out that Dean’s attempts to remain friendly certainly had an ulterior motive. He was hung up on Rory long after they broke up and was interested in rekindling a relationship with her, even as he prepared to marry Lindsay Lister. In the end, Dean turned out to be pretty awful, but he was a good guy initially. Fans could easily chalk up a lot of his bad moments to immaturity and inexperience.