Years after Rory Gilmore and Dean Forrester ended their ill-fated relationship, some Gilmore Girls fans still hold out hope that the duo will find their way back to each other. There is a good reason for that, too. Dean was Rory’s very first love. While Lorelai Gilmore insisted that Dean was the perfect “first boyfriend” for Rory, it’s pretty clear the pair were never meant to be.
Rory Gilmore and Dean Forrester had completely different goals in life
Rory and Dean had completely different goals in life. During their high school years together, it was pretty apparent that Rory’s Ivy League aspirations didn’t mesh well with Dean’s plans to attend community college and work. Dean wanted a wife that would stay home and take care of the house while he made money. While there is nothing wrong with Dean’s goals, they certainly weren’t in line with what Rory wanted.
Dean’s aspirations were actually more in line with Lindsay’s goals. In fact, Lindsay fit the plan he had in his head perfectly. While Jared Paldecki, the actor who portrayed Dean for five seasons, once described Dean’s marriage to Lindsay as a “cry for help”, they were well suited to one another. The real problem was that Dean was still pining over Rory when the popped the question.
Dean never took an interest in anything Rory was doing
When Dean and Rory first got together, they enjoyed a smooth first relationship. Dean was sweet in the beginning. He accompanied Rory to the dance he didn’t want to go to and stood up to Tristan for her. Aside from that, though, Dean had almost no interest in what Rory was doing with her life, and it showed.
By the time they tried to make their relationship work for the third time, Dean was over even pretending he was interested in Rory’s future plans. When Rory asked him what he thought of an article she wrote, he basically danced around commenting on it. One may even venture a guess that he didn’t bother to read it. Considering how important The Yale Daily News was to Rory, he could have at least made an effort to show he had read the piece.
Rory and Dean actually had nothing in common, other than the place they lived
When you break down Dean and Rory’s relationship and look at it from every possible angle, it becomes increasingly clear that Rory and Dean never actually had anything in common. Rory was a diligent reader who had no interest in sports. Dean, while presumably an average student, was more interested in sports and cars. The only thing that brought them together was their good looks and the fact that they both lived in Stars Hollow.
Once they headed into their college years, it became even more noticeable. Rory was on an Ivy League track, while Dean had completely walked away from academia and worked three jobs to make money. Both paths are entirely valid, but Dean had no understanding of Rory’s life, and Rory had no knowledge of his. They also didn’t seem particularly keen on learning more about each other, which ultimately led to their final breakup.