Reasons why Dean from Gilmore girls was an Awful Boyfriend™

… 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.

... true!

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.


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lumos is a GirlsAskGuys Editor
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Most Helpful Guy

  • Caveat: I've never watched the show. I don't know who these characters are. I was only dimly aware of the show's existence. This is ancillary to your topic, Lumos. This isn't about you, Lumos. This isn't about this Dean character. This isn't about the show.

    "Dean got visibly upset, and started frowning and pouting like an angry toddler."

    "Not to mention that you shouldn’t pressure someone or make someone feel bad for their (lack of) feelings."

    If all one does is visibly become upset when they're being rejected, they are NOT necessarily doing that to make you feel bad. They are doing it because THEY ARE HUMAN. They have feelings, they are understandably hurt, and quite understandably those emotions or bleeding through on their faces.

    I can't tell you the number of times I've heard both in real life and on GAG about someone rejecting someone, and the rejector mistakenly believes that because the rejected cried or teared up or his/her voice cracked, or he/she displayed some sign of pain, that it was automatically assumed the rejected was making an attempt to make the rejector feel guilty.

    I've rejected women who have cried or at least teared up, and because I knew them well, I knew they were NOT attempting to make me feel bad or pressure me. They were crying because THEY'RE HUMAN. They're not Vulcans. They have feelings. They are understandably hurt. Those feelings are understandably expressing themselves.

    Now, before anyone reading this thinks something like, "Well, *I'VE* been rejected, and*I* never cried in front of the person rejecting me," I have this to say: Whoopty fucking do. I've never cried in front of my rejectors either. That doesn't mean the rest of the world can behave that way. That doesn't mean the rest of the world *SHOULD* behave that way. It just means they're different from you and me.

    By the way, I am *NOT* talking about the jackasses who lash out with name calling, stalking, or worse behavior.

    Don't assume that because someone is visibly upset when you're rejecting them that they're trying to make you feel bad, or pressuring you, or trying to make you feel guilty. They're visibly upset because they're humans with feelings, and those feelings are being hurt, and quite understandably it's showing on their faces.

    That being said, it does sound like this Dean ain't such a good boyfriend.

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    • You put maybe a bit too much emphasis on him being visibly upset. My point wasn't that his pouty face made her feel guilty. My point was that what made her feel guilty were his actions and words that followed; he wouldn't let her explain how she felt, he jumped to the conclusion that since she wasn't able to tell him that she loves him it somehow automatically meant that she didn't want to be with him, and he also ended up dumping her over it. Him making a pouty face wasn't what I wanted to highlight, it was his temper tantrum. If he had let her explain her side of it, then maybe he wouldn't have ended up feeling so hurt. He overreacted.

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    • Well, again, that wasn't the point I was trying to make and I never wanted to make it seem like him being visibly hurt is what made Rory feel guilty, because it wasn't. I don't have a problem at all with people being visibly hurt. It's a completely understandable reaction. However, like in this situation, despite being hurt, he should have given Rory a chance to explain herself.
      I only put the "Dean got visibly upset, and started frowning and pouting like an angry toddler." sentence in there to give the readers a visual of what was going on and how he was reacting. Not because I think being visibly hurt is somehow inherently wrong. Just that in this case he was being silly.

    • " I don't have a problem at all with people being visibly hurt."

      Yes, I believe you. That's why I wrote, "This isn't about you, Lumos."

      I am not just speaking to you. I'm speaking to anyone who happens to read this, including some I'm sure who have felt that any display of hurt is an attempt to make the rejector feel bad. They should reconsider.

Most Helpful Girl

  • I love Gilmore Girls more than I can possibly describe in words, but Dean has always bothered me, for all of these reasons. Initially he seems great, and their relationship is innocent and sweet. But when problems start to arise, it reveals his issues as a boyfriend. Granted, towards the end of their relationship, he was justified in feeling hurt and jealous because of Rory’s behavior with Jess. She was obviously falling for him and I can’t blame him for sensing that and reacting. But other than that, he was out of line. And all the fighting really revealed his true colors. It bothers me that the show idealizes him as the perfect boyfriend, because he’s not. He’s actually the classic “nice” guy who seems sweet but presents major issues.

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What Guys Said 6

  • You do make some good points. When I compare the pros and cons of all three boyfriends, Dean gets the greatest amount of pros on my list. I guess you can say that all three were not 'The One' for her, but I am still on team Dean.
    It's definitely a great show. Do a myTake on Lorelai and her boyfriends. Luke, Christopher, Max. And who's team are you on?

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    • I’m team Jess post Stars Hollow. Once he got out of there and ditched the moody teen persona and actually did something with his life (wrote a book), all the good things about him really shone through. It’s a shame that we didn’t get to see more of the matured Jess and how he could have treated Rory.
      Thanks for your input :D

  • I'd be hovering too if I were him.

    I mean, we're talking about a drama TV series correct? If there's one thing that girls from those are good at, it's cheating without "technically" cheating.

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    • Rory never did that. Dean was just extremely jealous of the guys who were interested in her, and for no good reason. She tried to push them all away on several occasions but of course, Dean convieniently wasn’t hovering when that happened.

    • conveniently*

  • Lmfao when Jared is Dean here but he's Sam in supernatural

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    • I know haha, when I started watching Supernatural I had to perform quite a lot of mental gymnastics to get used to it and not mix up the names haha

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    • Exactly what I thought 😂

    • That's comdey gold tbh lol

  • I don't know who the Dean is and don't want to know just tell me how did you get that TM (trade mark) in title of this take

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  • I think you've spent way too much time watching this show.

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    • But it’s such a fun show :D great to have on in the background when you’re cooking, cleaning or putting on makeup.

    • I think I've watched the entire series through about ten times now. It's witty, entertaining, creative, and heartwarming. You can't beat it.

  • Dean wasn't so bad he Just happened to be in a relationship with a horrible person.
    Rory sucked and here are some reasons.
    1. She threw away her expensive education.
    2. She behaves like a spoilt child. We all know Lorelai isn't just any mom—she's a cool mom. But the friend/parent dynamic often gets blurred, and Rory takes advantage of their relationship. Whether she's inviting her grandparents to Lorelai's graduation or going to Anna Nardini's store after being asked not to, Rory's like, Boundaries? What are those? Not only does she not respect Lorelai's limits, but she's selfish and hypocritical. She throws tantrums when her mom doesn't take her dating advice—remember when she told Lorelai to slow down with Christopher (David Sutcliffe) in season seven, then got mad when they married in Paris?—yet freezes Lorelai out when she voices concerns about the many, many questionable decisions Rory makes with her own love life.
    3. She can't make it in the real world despite a yale education and yuppy connections.
    4. She had a poor upbringing with a flaky mom who was more intrested in being a "cool mom".
    5. Her mother gives her a poor example of being in a relationship with a man what with her Dad Christopher being a dead and the conga line of deadbeat would-be stepfathers that followed. Rory like her mother wasted her twenties on the cock riding carousel until she got the wall after reaching her thirties and got pregnant to Logan hoping to trap him and get him to leave his fiancee. After turning Logan's marraige proposal down years ago she basically wants him to provide a life of comfort now that she has failed to make it in the real world. She will try for the guys that weren't good enough for her in her teens and twenties like dean or jess or maybe the guy who's name nobody can remember if she fails to steal wealthy alpha male Logan from his fiancee.
    6. she's a homewrecker. She sees nothing wrong or immoral with sleeping with a married or engaged man. Obviously the cheater is the most immoral then again Rory cheated on her then current boyfriend with Logan.
    7. She is a criminal. She Stole a Yacht and Dropped Out of College Just Because Her Boyfriend's Dad Told Her She Was a Crappy Journalist. Being told you suck at your dream job is a bummer for sure, but let's be real—Mitchum was right. While all her friends were making moves to score internships over summer, Rory headed off to Europe with her grandmother. When she finally did land a gig...

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    • ...(and only because of her boyfriend), she spent the whole time playing personal assistant and brown-nosing the staff, instead of going out in the field and actually finding original stories to write about.
      8. She's the Poster Child of White Privilege
      One of the most infuriating aspects of Rory's character is her inability to recognize just how privileged she is. Both Rory and Lorelai like to believe they're more connected to the working class because of Lorelai's effort to distance themselves from Richard and Emily's money through the years, but they have no problem taking family money when it's needed or given— like paying for prep school, getting a new car, tuition at Yale, trips to Europe—the list goes on.
      When we left Rory at the end of the series, she was taking off on the campaign trail to cover then Senator Barack Obama's presidential campaign, but only after she disappointedly had to tell her grandparents she couldn't take them up on their offer for a free apartment...

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    • Did you even read my take? Lol no wonder you’re anon

    • I read it. Its a goodtake I just don't agree.

What Girls Said 5

  • THANK YOU. I always hated Dean. He's a self-proclaimed "nice guy" and a controlling, emotionally manipulative piece of trash. He's a crybaby beta and in every scene, I have the urge to strangle him lmfao. Literally every other guy on that show was better and more mature than Dean. I'm Team Jess cause he is always genuine af and actually proves to be a good man as the show progresses. He really understands Rory and actually listens to her unlike Dean... and he's much better looking and smarter. Honestly, Jess is now too good for Rory and I feel sorry for him... -_- Lmao I could rant about Dean forever.

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  • I really loved this show and was sad when it ended.

    I'm glad someone feels the same way as I do about Dean. I never rlly liked him and prefered Jess over him.

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  • Yep Dean was kinda trash.

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  • Yep Dean was kinda trash. Hkjjhjf

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  • Is it bad that I never really cared to watch that show.

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