Top 10 Times Dean Was the Worst on Gilmore Girls

We know from practically the moment we meet Rory in the first season of “Gilmore Girls” that she's destined for great things at an Ivy League school. Her dream has always been to go to Harvard, and throughout the first few seasons she bases all her life decisions on achieving that goal. When it comes time to get serious and work on her application, however, Dean begins to put doubts in her mind about their relationship’s future. After she meets with a Harvard alumnus, he brings up the impending end to their romance, totally ruining her vibe.

In the first season of the show when Rory and Dean have just started dating, they, along with Lorelai, watch an episode of “The Donna Reed Show” together. While Lorelai and Rory mock the antiquated notions of how women are portrayed on the show, Dean defends the concept of a woman who wants to make supper for her family. This entire episode shows how not woke Dean is, as he defends a woman’s “right” to want to make sure her husband has a nice dinner on the table when he gets home from work—and expresses that he thinks it’s a “nice” concept.

Rory and Dean are high schoolers when they begin dating, so it makes sense that they’re excited to celebrate the momentous occasion of their three-month anniversary. Dean makes a pretty over-the-top gesture by restoring a vehicle for Rory, but not only that, he also tells her he loves her—then can’t understand when she isn’t ready to say it back. The two end up breaking up because they’re not on the same page, and Dean is visibly frustrated that Rory isn’t as serious about the relationship as he is. Let’s all remember that they’ve been dating for three months!

In this season two episode, Lorelai goes away for a spa weekend leaving Rory with a rare opportunity to have the house to herself. She’s excited to order takeout and have some alone time, but Dean insists on coming over even after she makes it clear that she doesn’t want him to. This is just one instance of Dean showing how clingy he is. Later in the same season, when he feels like he’s losing his grip on their relationship, he calls Rory a whopping 14 times when he can’t manage to get in touch with her.

From their very first interactions, Dean shows some red flags in terms of his behavior towards Rory. He openly admits when they first start talking that he’s been “watching her” and has been closely observing her behavior for some time. Rather than being creeped out by this, Rory is charmed that he has noticed her. This is the classic sort of behavior that can fly in a romance movie or TV show storyline but would be considered pretty problematic in real life. When you’re interested in someone, perhaps trying talking to them instead of stalking them.

#5: His Jealousy Over Tristan Dugray Various Episodes

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Throughout his time with Rory, Dean shows jealous behavior on a number of occasions. Starting in the first season, he gets into a fight with Tristan at Rory’s dance - though to be fair Tristan was clearly trying to instigate a conflict. As the story went on, however, Dean continued to be jealous of Tristan even when there wasn’t anything going on between him and Rory. Should Rory have told Dean about the kiss that took place while they were broken up? Absolutely. But Dean’s behavior was still over the top. Later, when he becomes jealous of Jess, he starts acting out in the same ways all over again.

#4: Being Awful to Lindsay Lister Various Episodes

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Dean having an affair with Rory is terrible -don’t worry, there will be more on that later - but the way he treats his wife, Lindsay, throughout the process makes the entire situation even worse. Lindsay hasn’t done anything wrong and in fact has only tried to be a perfect wife all along. But after Dean sleeps with Rory, he basically gaslights his wife and gives her a hard time when she answers his phone for him. Obviously he’s on edge because he doesn’t want to get caught, but let’s just say he totally deserved what he had coming to him.

#3: Not Letting Rory Study Various Episodes

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Despite the fact that when they met Rory was a teen whose focus was on getting into a good college, Dean managed to try to make her entire life revolve around him. In season two when Rory starts to worry that she doesn’t have enough extracurriculars to make her application stand out, Dean seems to only focus on the fact that she’s bailing on plans with him. For Rory, priority number one is getting into Harvard, yet Dean can’t seem to handle taking the second-place spot, and often makes a big deal about it.

In the first season, Dean makes a big deal about going to Rory’s dance with her at Chilton. By season three, once he’s desperate to make their relationship work, they go to another dance together: the Stars Hollow Dance Marathon. At this point Dean has—reasonably—become suspicious of Rory’s feelings for Jess. Rather than deal with the matter privately, however, he breaks up with her dramatically in front everyone at the Dance Marathon. Sure, Rory should have sorted out her relationship with Jess by this point, but Dean screaming at her and publicly shaming her was absolutely not necessary.

#1: His Affair with Rory “Raincoats and Recipes”

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There were definitely two people to blame in this situation, but Dean was married when he and Rory slept together. So this makes him slightly more guilty in the fact that he was the one cheating on a partner while Rory was single. Dean and Lindsay’s relationship seemed somewhat doomed from the start because they chose to get married so young—not to mention the fact that he was clearly still harboring feelings for Rory at the time. Rory and Dean sleeping together when he was married was obviously a terrible idea, and the way he behaved afterwards and the way he treated his wife made the entire affair all the more unforgivable.