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17 Reasons Jess On 'Gilmore Girls' Was The Most Toxic Boyfriend Ever

This may put me in the minority in the Gilmore Girl fan world, but Jess Mariano was not my favorite when it comes to Rory’s boyfriends. When I first watched the show back in my early twenties, I guess I had a little bit of a crush on the guy. I mean, he’s easy on the eyes and he’s got that bad boy charm we’ve all been programmed to kind of enjoy. And yes, he has good taste in music, and he’s well-read and all. But the fact remains, Jess Mariano is the worst.

That’s not to say Dean or Logan were all that much better, but there’s already been plenty of analysis when it comes to Rory Gilmore’s boyfriends. They were all teens (and young adults) on the show, so of course they were all bound to make plenty of mistakes, and they did. We’ve all been there. And this also isn’t to say that I totally hate Jess, because I still enjoy him to an extent. But of all of Rory’s beaus, I find him to be the most toxic, borderline-abusive jerk of them all. And while he doesn’t ever cheat on her (honestly, I can forgive Logan’s indiscretion because to me it did seem like they’d broken up but that’s a conversation for another day), he does basically toy with her and treat her like crap, only trying to make up for it when it’s obviously way too late. When it comes to the way Jess treated Rory, she could certainly do better. If you’re skeptical, let’s revisit their relationship:

He Started Going After Rory Even Though He Knew She Was Seeing Someone

When Jess first arrives in Stars Hollow, he is almost immediately intrigued by Rory. Within days, she introduces Jess to her boyfriend Dean. Jess decides that this, of course, doesn’t matter, and starts finding ways to move in on Rory anyway. Not cool.

And His Way Of Getting This Was By Belittling And Humiliating Dean Every Chance He Got

So many examples of this, but here’s the first one that comes to mind: In the episode “A-Tisket, A-Tasket,” Jess puts his plan to get Rory away from Dean in action by out-bidding him on her basket at the town auction. Dick move, Mariano. And frankly, a perfect example of the sexist mindset that underscores his whole strategy to "win over" Rory: that women can be easily swayed away from one man and into the arms of another if the new guy just shows up a lot and talks shit about the first guy.

He Had Zero Respect For Everyone, Even Lorelai

Dude is basically out to insult or disrespect everyone on the show except himself. When Rory tries to get him and Lorelai to bond by having him clean the Gilmore’s rain gutters, he decides instead to go and help himself to a beer from the fridge. Like, I get it. He’s a teenager. But still. And the way he talks to Lorelai and Luke (and especially in reference to their friendship) is always way out of line. Respecting someone you're dating doesn't mean barging in and creating discord within the most important relationships in their lives, and that's what Jess shamelessly, habitually does with Rory.

He Crashed Her Car. HE CRASHED HER CAR.

When Rory tries to tutor Jess, he’s bent on finding any way out of it, and convinces Rory to go get ice cream with him instead. Rory ends up letting him drive (WHY, RORY? WHY?!) and he gets distracted eating the damn ice cream and crashes her car. The beautiful classic car that her boyfriend freaking built for her because dude was the most amazing first boyfriend a girl could ever have (totally with Lorelai on this). And then, instead of facing the music (and checking to see how Rory is since she broke her actual arm in this accident meaning it was no small accident), or offering to help pay for the car (since she is now car-less), he just dips out. (I'm sorry, how are any of you guys Team Jess again?)

He Never Knew How To Apologize

My memory is a bit rusty on this, but how often did we see Jess apologize for all his lousy behavior on the show? I’m guessing any apologies (that were actually sincere) were few and far between and less about him genuinely being sorry and more about him realizing that even Rory "You Can Do Whatever You Want, Jess, It's Fine" Gilmore would need him to make occasional, paltry attempts at remorse if he was going to be allowed to continue touching her headband.

He Was Negative About Pretty Much Everything

Jess was always whining about everything. He hated living in Stars Hollow. Hated everything about the town. Hated Dean. Hated Luke (sometimes). Hated Lorelai. Hated school. When Luke tries to congratulate him for getting employee of the month, he hated that, too. The chip on his shoulder was nearly permanent (except once he dated Rory, and then he was at least a little less of a jerk about everything...in front of her, anyway). Seriously though, why would anyone want to be around that for long?

Plus, The Kid Had Major Anger Issues

Jess always had a fully crap attitude, and was apparently constantly getting into fights at school (one of which Dean tried to break up, at which point Jess tried to punch him, too). Granted, the big Jess/Dean fight scene got started because Dean punched him (but in his defense, Jess left a bedroom he and Rory had been in and Rory is crying so at this point Dean assumes what anyone else would, which is that Jess disrespected Rory in some way, which he did, so I give Dean a pass on that one). I’m sure he was more than happy to fight, anyway.

He Inadvertently Caused Rory To Miss Her Mother’s Graduation

Alright, so this is more on Rory than it is on Jess, but it's a clear testament to the impact that toxic people have on the people around them. Basically, Jess called Rory up on the night before her mom's big day and the next day, Rory cut school (WHAT?) to take a bus to New York (WHAT WHAT?!) just to spend some time with the dude. And then, of course, he just acted like he didn't have anything to do with it (as though he hadn't been playing mind games with her the whole time). Bah.

He Treated Women Like Crap In General

For a while, Jess dates this girl Shane (obviously a rebound after his almost-relationship-but-not-quite with Rory). He treats her like so much garbage it’s not even funny. At one point, he even hides her in a closet in Luke’s apartment. He even takes her to go and creep-watch Rory at the Dance-a-thon, and dumps her like it’s no big deal when Dean breaks up with Rory and he realizes now is his chance. Yuck. Again, it really doesn't say much about Rory that she even likes this dude. Like, does she think that she's so exceptional that it's somehow OK for her to be the only person that Jess even halfways treats decently (if you can ignore him being manipulative, divisive, and wholly toxic to every single part of her life that means anything to her)? Or is she just so oblivious that she doesn't see the fact that he treats women like shit? What's her deal here?

He Could Not Make Nor Stick To Plans

When they finally do start dating, Jess’s inability to make concrete plans with Rory (that aren’t vague and all, “let’s hang later”) starts to really bother her. And why wouldn’t it? Plans make life a little more manageable. You can plan the rest of your day around them. Having them means not having to spend time waiting around for a phone call or visit (because you know when to expect it).

...But Expected Rory To Be There Whenever He Wanted

In one episode, Rory gets fed up waiting for Jess to call so she goes to a hockey game instead. Jess is obviously annoyed that she’s not around when he wants her, and brings her concert tickets, which are supposed to make everything alright again. They do, because Rory is 17 and not wise enough to realize he’s a manipulative jerkface. Worse than that, she ends up making up excuses for his behavior when others around her notice he’s being a jerk. Wake up, Rory! You’re smarter than this!

He Tried To Pressure Rory To Have Sex With Him

SERIOUSLY, FRIENDS. This is probably my main issue with him. In the house party episode where Jess is all blah because he knows he’s not going to graduate, he totally acts like a jerk to Rory. They both end up going into a bedroom and start making out. He wants things to go further; she doesn’t. She stops him, and suddenly he goes into jerk mode. Watch the scene above and tell me that isn’t screwed up.

...And Then Yelled At Her When She Wouldn’t

Still regarding the last scene I mentioned, but these are two separate but equally messed up things to do to your girlfriend, who has been nothing but kind and understanding toward you. One thing is to try to pressure someone (which is awful in and of itself). And then another is to shout at her afterward for it and make her feel like crap. This is not OK. This is not healthy. It really freaks me out to think that there are so many girls out there idolizing this guy who at one point acts borderline rape-y and is verbally and emotionally abusive to boot. Nope. Nuh-uh. Not OK.

He Could Not Communicate At All. AT ALL.

This is an overlying theme throughout the show for Jess. For all his sarcastic verbosity, he sucks at communicating important shit. Like how he’s failing high school. And how he won’t be taking Rory to prom (which resulted in the aforementioned incident, although that’s NOT an excuse). And how his father showed up randomly. And how he left to go see his dad and missed Rory’s graduation. And, and, and...

He Didn’t Have The Courage To Break-Up With Rory In Person, Or At All, Really

They had one major fight and instead of, I don’t know, going over to Rory’s house to have a chat on the porch about their major miscommunications, he figured, “Nah, I think I’ll go kick it with my dad and see what that’s all about.” Could have at least left her a note, jeez.

He Showed Up Unannounced, Convinced That A Declaration Of Love Will Be Enough To Make Her Forget What A Loser He Was

But this time, Rory was older and wiser and realized that no, actually none of his bullshit is OK. BYE.

And Finally, Even Years Later, He Tried To Act As Though He Knew Her Better Than She Knew Herself

I was excited for Jess to come back in general in the final season, but I didn't dig the way he went about calling Rory out on her whole throwing-caution-to-the-wind phase. Sure, she had always been a meticulous planner and college had always been her dream, but things change. People change, especially young adults. Oh, suddenly because she wasn't doing things the way he wanted and expected her too, it was his job to tell her how much she was screwing up? Yeah, no. This from the guy who left her high and dry on a number of occasions and was expecting her to understand that he'd "finally changed"? Sigh. Jess never stopped being a bottomless hell-pit of worthlessness and acted as nothing but a painful, derailing force in Rory's otherwise stable life. End of story.