Years after Rory Gilmore and Dean Forrester ended their ill-fatedrelationship, some GilmoreGirls fans still hold out hopethat the duo will find their way back to each other. There is a good reason forthat, too. Dean was Rory’s very first love. While LorelaiGilmore insisted that Dean was the perfect “first boyfriend” for Rory, it’spretty clear the pair were never meant to be.
Rory Gilmore and Dean Forrester had completely differentgoals in life
Rory and Dean had completely different goals in life. Duringtheir high school years together, it was pretty apparent that Rory’sIvy League aspirations didn’t mesh well with Dean’s plans to attendcommunity college and work. Dean wanted a wife that would stay home and take careof the house while he made money. While there is nothing wrong with Dean’sgoals, they certainly weren’t in line with what Rory wanted.
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Dean’s aspirations were actually more in line with Lindsay’sgoals. 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 marriageto Lindsay as a “cryfor help”, they were well suited to one another. The real problem was that Deanwas 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 smoothfirst relationship. Dean was sweet in the beginning. He accompanied Rory to thedance 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, andit showed.
By the time they tried to make their relationship work forthe third time, Dean was over even pretending he was interested in Rory’s futureplans. When Rory asked him what he thought of an article she wrote, hebasically danced around commenting on it. One may even venture a guess that hedidn’t bother to read it. Considering how important TheYale Daily News was to Rory, he could have at least made an effort toshow he had read the piece.
Rory and Dean actually had nothing in common, other than theplace they lived
When you break down Dean and Rory’s relationship and look atit from every possible angle, it becomes increasingly clear that Rory and Deannever actually had anything in common. Rory was a diligent reader who had nointerest in sports. Dean, while presumably an average student, was moreinterested in sports and cars. The only thing that brought them together wastheir good looks and the fact that they both lived in Stars Hollow.
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Once they headed into their college years, it became evenmore noticeable. Rory was on an Ivy League track, while Dean had completelywalked away from academia and worked three jobs to make money. Both paths are entirelyvalid, but Dean had no understanding of Rory’slife, and Rory had no knowledge of his. They also didn’t seem particularly keenon learning more about each other, which ultimately led to their final breakup.
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