From Dean's feelings for Rory to Lindsay's wildly unrealistic expectations, every Gilmore Girls fan knew this marriage wouldn't last.
In the third season of Gilmore Girls, Rory found out that Dean had moved on with her former classmate, Lindsay Lister. The two looked perfect together and incredibly smitten, which made Rory feel a whole mix of emotions. Shortly after the two started dating, they got engaged, and the two were married by season 4.
Fans (and Rory) were shocked by their whirlwind romance but the truth eventually unraveled itself. As time went on, Dean and Lindsay appeared to be miserable. It didn't help the fact that Dean was still chasing Rory around town. And as quickly as they started, the two were done by season 5. Lindsay and Dean were doomed from the start.
Dean and Lindsay were right out of high school when they got married. Being around 18 and 19 years old and being married is hard - especially today, when the expectation is to wait until a lot later in life. It's hard to settle down, get a house, and lease a car when a person doesn't have much life experience. Whether they divorced over Rory or something else, it was bound to happen eventually due to their age.
When Dean and Lindsay became serious, he told Rory that he had a five-year plan and that she shouldn't worry. It's assumed that his plan involved parts of his marriage, but also finishing college.
Down the line, however, Dean told Rory that he was taking time off from school in order to work more because Lindsay had certain expectations in their marriage that weren't being met. Once Dean started working more and Lindsay didn't contribute, it's fair to see how their wires crossed and they just didn't have the same vision of their future.
Dean and Lindsay's marriage was never going to thrive until Dean moved on from Rory. He must have thought that once Rory went away for college, he wouldn't see her as much and be able to get over her. But that wasn't the case. Rory was always in Stars Hollow and saw Dean around town frequently. Instead of keeping a safe, friendly distance from Rory, he went out of his way to see her (the Dragonfly Inn, Yale, etc...). Dean should have realized on the night of his bachelor party that he was still hung up on his ex-girlfriend and shouldn't have married Lindsay.
It was clear from the start that Lindsay's parents had a heavy influence on their relationship. They were heavily involved in the wedding, supported Dean while they were engaged, and were even entangled in their demise.
Lindsay's mom joined her when she visited Dean at work, and it's safe to say that wasn't the only time during the week that Dean was up against his wife and mother-in-law. It makes fans wonder if Dean and Lindsay ever had a say for themselves as a couple.
Dean was never too sure about his college dreams but once he and Rory broke up, he made the decision to apply to four-year universities. On the night that Rory was accepted into Harvard, Dean told Rory that he was also accepted into Southern Connecticut State and was thrilled over it. However, whether Lindsay liked it or not wasn't said. Considering the fact that Dean left school to work more, it seems like Lindsay was more interested in her husband working and bringing home money than getting an education.
In "That Damn Donna Reed," Dean told Lorelai and Rory that he didn't see anything wrong with Donna Reed's lifestyle. As a man, he also enjoyed the thought of a woman staying home to cook, clean, and take care of the kids. His mother was also a stay-at-home mom and he wouldn't have it any other way. And upon meeting Lindsay, that seemed to be her vision as well. But somewhere down the line, Lindsay wanted the wealth and Dean's presence all at once, and didn't seem to realize that if she wanted the money, he would need to be out working to get it. Being a stay-at-home wife at 19 years old was not realistic for a couple like Dean and Lindsay.
It was shocking when Dean pulled Rory aside and told her that he and Lindsay were engaged. They were only dating for a few months and were so young, why the rush? Rory didn't react well to the news and there have been a few theories as to why Dean proposed.
Some fans told Reddit that Dean proposed spontaneously after the fight against Jess at the house party. Perhaps Lindsay was livid that Dean cared so much about Rory, and in an attempt to save her from leaving him, Dean proposed. Others think there was a pregnancy scare for the couple and that getting engaged was the right thing to do.
There was nothing wrong with Dean being friends with Rory during his marriage to Lindsay. However, there was something wrong with the intentions of the friendship when Dean was hiding it from his wife. Lindsay didn't know how close Dean and Rory were until she overheard Rory and Lane talking poorly about her relationship. It was then that she realized Dean told Rory all about their marital issues, causing insecurities.
Clara was Dean's younger sister who popped up every now and again. Rory and Clara weren't particularly close but they liked each other. When Dean and Rory began their affair, which inevitably broke up Dean and Lindsay's marriage, Clara admitted to Rory that she liked her way better than she liked Lindsay. Knowing that even Dean's family wasn't supportive of Lindsay and were always #TeamRory had to have taken a toll on his marriage.
Did Lindsay and Dean love each other or did they just love the idea of each other? It seems like they both dreamed of being in a marriage like their parents but didn't feel as strongly for each other as they wanted to. After only dating for a few months before getting married, Dean and Lindsay didn't know each other that well. They simply liked the idea of being married.
