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

Almost two decades after it all happened, Gilmore Girls fans are still perplexed about one major storyline. They can’t wrap their heads around why Dean Forrester decided to marry then cheat on Lindsay Lister. The pair were engaged after just months of dating. They married shortly after graduating high school. While the reason for the marriage is never explained, fans have some theories about what prompted their engagement.

One Reddit fan theorizes that a pregnancy scare might have forced him into an engagement

A Reddit user has an interesting theory about Dean and Lindsay’s marriage. The user suggests Lindsay and Dean’s rushed wedding was the result of a pregnancy scare. They point out that Dean, ever the traditionalist, would have felt compelled to propose if his girlfriend was pregnant. They also point out how quickly the marriage took place. Dean proposed in May or June of his senior year of high school. They were married by the following fall.

The theory, while interesting, seems unlikely. Dean and Lindsay never had any children, nor was it ever suggest that they were sexually active before their marriage. Lindsay’s mother, Theresa, was clearly jazzed about the idea of the pair having kids, but they never got around to it. If a pregnancy scare had occurred, it likely would have been mentioned in the show. 

Dean’s marriage to Lindsay might have been an overreaction to being dumped by Rory

It seems more likely that Dean asked Lindsay to marry him as a severe overreaction to his breakup with Rory Gilmore. Think about it, Dean and Lindsay had dated for less than six months when he proposed. They started dating within two months of Dean and Rory ending their long relationship, and Dean still seemed to have a problem with the fact that Rory was with Jess Mariano.

It seems possible that Dean, still battered from his breakup with Rory, decided he wanted the security of a long-term relationship. Since his parents were happily married, he may have thought that was the best way to get what he wanted, even if it was not with the girl he necessarily wanted.

Dean could have been trying to prove that he was over Rory

The timing of Dean’s proposal is a bit suspect, points out another Reddit user. Dean proposed to Lindsay right after he and Jess fought at the party of a high school friend. The fight, which was prompted by Dean seeing Rory crying, was so bad that somebody called the police, and the house was completely wrecked.

Is it possible that Dean and Lindsay argued over Dean’s feelings for Rory? If they had an off-screen argument, it’s possible he proposed to prove he was over Rory. It also seems likely that Dean did not want Lindsay to end their relationship, so proposing was a way to ensure no one would ever break up with him again.