Though Gilmore Girls' Dean Forester appears to be Stars Hollow's golden boy at first glance, some serious flaws lie beneath his "perfect first love" image. He isn't just the athletic teen who teaches Rory Gilmore what love is, but is instead a person with underlying insecurity and jealousy that goes way beyond what can be deemed acceptable. He has redeeming qualities (like genuinely caring for Rory and going out of his way to take care of her), but he also has an unwavering devotion to his increasingly outdated vision of their relationship.
While some of the things he does all the way up to Gilmore Girls season 5 can be chalked up to just being an insecure and immature teenager, that's not the case for everything. Simply put: at times, Dean is just the worst.
Dean can be clingy and possessive
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One of the biggest red flags throughout Dean's Gilmore Girls story is his clingy and possessive nature. He struggles with Rory's independence, getting upset when she prioritizes schoolwork or spending time with Lorelai. Both Jess and Logan are better about allowing Rory to be an independent individual, without feeling threatened when she prioritizes other things (or people) in her life.
Dean resents and complains about Rory's ambitions
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Simply put, Dean doesn't accept how talented and driven Rory is! When Rory panics about getting into Harvard, Dean is unsupportive of her dreams and complains about how busy she is. Instead of recognizing that Rory's ambitions are important to her (and that they don't mean she cares about Dean any less), he becomes threatened by her goals and frustrated that they have different priorities.
Dean tends to react in anger
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When Rory tells Dean she broke her arm while she was with Jess, Dean *completely* loses his cool. He ends up kicking a duffel bag out of anger, which feels like an unfair reaction. Rather than addressing the situation calmly and finding out exactly what had happened, Dean reacted terribly and inappropriately.
Dean has a hard time respecting Rory's boundaries
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When Rory expresses that she wants a quiet night in, Dean shows up at her house anyway. When she's busy and not answering the phone, he decides to call her 14 times! Throughout Dean's Gilmore Girls arc, he's unable to accept that she has a life of her own and can't always be available to talk to or be with him.
Dean pressures Rory into saying "I love you"
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Saying "I love you" for the first time should be something incredibly special and heartfelt — and shouldn't come at the request of someone else. Dean doesn't seem to get this memo, as he pressures Rory to say "I love you" to him on their three-month anniversary. When Rory expresses that saying it is hard for her because of what happened with her parents, Dean's incredibly dismissive of her feelings.
Dean is over-the-top jealous
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When Rory stars in Romeo and Juliet at school, Dean's unfairly jealous of her playing a romantic part opposite Chad Michael Murray's Tristan. Rather than showing any type of maturity and recognizing that it's just acting, Dean goes so far as to come to every one of her rehearsals.
Dean is a little too old-fashioned
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If both parties in a relationship choose to conform to typical gender roles, that's totally fair. However, Dean's a little too hell-bent on the idea of women being the ones cooking and cleaning. He's unable to see the sexism of The Donna Reed Show and isn't very willing to listen to Rory and Lorelai's take on it.
Dean publicly embarrassed Rory when he broke up with her
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Dean doesn't have to stay in a relationship if he's not happy any more, but breaking up with Rory in front of everyone in the middle of season 3's dance marathon is just plain wrong. It proves that he tends to act out of emotion, with little consideration to whether or not it's the right time or place. He humiliates Rory unnecessarily, and could have just waited to end things with her later in private.
Dean was a horrible husband to Lindsay
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Dean marries Lindsay even though he knows he's still in love with Rory, and he treats Lindsay horribly. He snaps at her for no reason and resents the fact that he has to financially support her — even though he chooses to marry her!
Dean has an affair
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The cherry on the top of this horrible cake is that at the end of Dean's Gilmore Girls plot, he ends up cheating on poor Lindsay with Rory. Afterwards, he gaslights Lindsay and makes it seem like she's in the wrong for unknowingly picking up his phone to discover the affair. He never should have allowed things to happen between him and Rory when he was still married, and it emphasizes how bad Dean's judgement can be.
What's your opinion on Dean's Gilmore Girls story? And who's your favorite of Rory Gilmore's boyfriends?
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