… and actual garbage.
Most people I know would consider Dean to be the best boyfriend Rory ever had, because he was just so nice. Not like that asshole Jess who would constantly get into fights, act like a cranky bad boy teen and judge Rory for her interest in town activities. Or that rich boy Logan who has had everything in life handed to him on a silver plate, whose favorite pastime is to be pretentious af, get drunk, waste lots of money and judge people who aren’t as rich as him. Well, I’m here to ruin that image you have of Dean by pointing out all the major red flags and flaws so many people have swept under the rug throughout the years, because they were too busy focusing on the fact that he would occasionally buy Rory ice cream or “put up” with her and her mother’s quirks. Ugh.
!!! Major spoilers by the way, but I feel like that kinda goes without saying, also this show is nearly 20 years old (holy shit) so if you haven't watched it by now... you're missing out. Maybe also don't read if you don't want to be spoiled. Fanx.
1. His possessiveness over Rory and his inability to listen to her
Whether Rory was dealing with asshole Tristin or mysterious Jess, Dean was always hovering passive aggressively in the background, always assuming the absolute worst about what Rory was doing. This often resulted in Dean shouting at Rory before even hearing her out or letting her explain. It even got to the point where he felt like he should intrude on Rory’s play rehearsals just so that he could watch over Tristin and make sure Rory didn’t do anything with him. Which, surprise surprise, just ended with Tristin provoking Dean and there being another fight. Instead of trusting Rory or listening to what she had to say, he always lashed out and refused to let her explain her side. In the end, Rory even felt like it was better to hide things from Dean because she was too scared of getting into another fight.
A prime example is when she had told him that she wanted a night to herself – which she truly did – but because of circumstances beyond her control, both Jess and Paris ended up crashing at her place with a ton of food. Then Dean, unbeknownst to the situation at Rory’s place, wanted to come over with some ice cream. Rory freaked out and tried to shove Jess out of the house before Dean got there, but it was too late. Dean saw Jess, Jess left (after provoking Dean for a little bit), and then he started yelling at Rory before she even got a chance to explain. He stopped yelling only when Paris came up with a fake excuse as to why Jess was there, claiming that she was into him and had asked Rory to invite him. Only then did Dean calm down, but he still acted cold towards Rory. This sort of behavior is just not cute. Nothing about being this jealous, stubborn, aggressive, and unwilling to listen is good boyfriend behavior. At one point, he even threatened to kill Tristin – drama queen much? You should be able to voice your concerns without raising your voice or becoming unnecessarily aggressive. Jumping to the worst possible conclusion is also not cute, as it only unveils your ugliest insecurities and trust issues.
Yeah... such a nice guy.
2. The fact that he tried to make Rory feel guilty because she couldn’t say “I love you” back
This happened when they celebrated their 3-month anniversary. First, they had a nice dinner at a restaurant, and afterwards they were going to watch the bonfire. But before the bonfire started, Dean surprised Rory by taking her to a junkyard and showing her the car he was building for her. She got very excited, and they ended up sitting in the car for a bit while talking. During their talk, Dean told Rory that he loved her. Rory was shocked and didn’t know how to respond. She couldn’t say “I love you” back, most likely because she wasn’t completely sure if she loved him yet, and because she thought it was a thing that shouldn’t be thrown around so easily.
Dean got visibly upset, and started frowning and pouting like an angry toddler. Rory got incredibly sad and wanted to explain, but again Dean didn’t hear her out and just wanted to go home. In the end, Rory revealed to her mom that he had dumped her over this. Not only is that probably the biggest overreaction ever (hello, they had only been going out for 3 months) but breaking up on your anniversary is probably the douchiest thing you could do. And without even trying to talk things out. Not to mention that you shouldn’t pressure someone or make someone feel bad for their (lack of) feelings. Dean said that he felt like an idiot for saying that he loved her while she couldn’t say it back. Yeah, he should feel like an idiot, because what he did afterwards truly makes him deserving of an award in idiocrasy. He has probably one of the most fragile egos ever. Obviously, it might not be super nice to not have your feelings 100% reciprocated, but he should have been able to take a step back and realize that Rory will eventually be able to say it back, and to just give her some time.
3. Him demanding that Rory spend all her free time with him
When Rory was scrambling to figure out what extracurricular activities she should join to have a better chance at getting into Harvard, Dean was upset that Rory didn’t have as much time to hang out with him anymore. Instead of supporting her and her ambitions, he again tried to make her feel guilty and tried to make it all about him. This time for not prioritizing him over her education and future. Being in a relationship means sticking by your partner’s side through thick and thin. That means that sometimes your partner might be busier than normal. Maybe you’ll end up feeling a little bit left out or neglected, which is understandable. What’s not understandable, however, is taking these feelings out on your partner and trying to make them feel bad for being busy – something they most likely can’t control very much.
4. His possessiveness as an ex
After Rory and Dean had broken up for a second time, Rory ended up getting into a relationship with Jess. And although Rory was quite a bit of an ass for the last part of her relationship with Dean (she had feelings for Jess but was too much of a wuss to break things off), Dean became just a tiny bit too salty. He confronted Jess late one evening when Jess was taking out the garbage. Completely unprovoked, he tried to get Jess to fight him. This time around, Jess wasn’t too keen on trying to fight with him anymore. Dean had no business behaving that way towards Jess, and even though Jess is also a bit of an asshole, Dean could have taken the high road and tried to just move on from the whole thing. He had already given the relationship with Rory a shot twice, and at this point you’d think that he’d be so over it that he wouldn’t even bother giving Jess this kind of attention.
Rory and Dean later became friends, as they thought the town is too small and they’ll be bumping into each other anyway, so might as well be friendly towards one another. And although I see the logic in that and why both Rory and Dean would be comfortable with it, it was also obvious that a part of Dean wanted them to be friends just so that he could get back at Jess and taunt him. This could be seen during the winter festival when Dean was waving his friendship with Rory in front of Jess’ nose very passive aggressively. Absolutely pathetic.
5. Cheating and being emotionally abusive (this time with Lindsay)
Once Rory and Dean had broken up “for good”, Dean quickly married another girl, Lindsay. She ended up living the Donna Reed lifestyle that Dean wanted in a girl, by being the perfect housewife who cooks roast beef for her husband every night. Dean ended up cheating on Lindsay with Rory, which Lindsay later found out about. We, as viewers, don’t get to see a whole lot of what goes on in their relationship, but it’s clear that Dean’s heart and mind isn’t totally in it and that he’s still somewhat pining after Rory. One night, while Lindsay was home alone (and this was after Dean cheated with Rory), she answered Dean’s phone. Rory had called him, expecting Dean to answer, but when Lindsay answered she freaked out and hung up. Later when Lindsay told Dean about getting that weird call, Dean freaked out and yelled at Lindsay for answering, making up an excuse that it could have been his boss with an important job offer. It was clear he just didn’t want her to find out about the affair with Rory and therefore wanted Lindsay to not touch his belongings.
... Rory on what Lindsay should do with Dean.
What I love about Gilmore Girls is the fact that every character is flawed in some way. Obviously it wouldn’t be a very realistic (or fun) show if every single character was perfect and had perfect relationships and friendships. However, something that I have quickly grown tired of is how both characters in the actual show (such as Lorelai) and people who have watched the show are glorifying Dean and making him out to be this wonderful boyfriend who always treated Rory with respect. That simply isn’t true. He was flawed, just as anyone else, both as a person and as a boyfriend. I started watching this show when I was very young, and the more I’ve re-watched it, the more I start to see the depth of all the different characters and their off-putting behaviors.
Rory is by no means a saint either, I could very much write about how she was a bad girlfriend too, and I probably will write a take about that in the future. I’m currently re-watching the show, and the chapter with Dean just ended. As I keep watching, I will collect some mental notes regarding Rory’s behavior as a girlfriend and will later on write a similar list about her.
Yes I'm obsessed with the show shut up.