His smile could easily make a girl melt in a matter of seconds. He was passionate about books, he enjoyed intellectual conversations and he loved clever literary references. He was also witty and adventurous, and he had that bad boy charm that no one could resist. Jess Mariano was essentially every book nerd’s dream guy (and arguably one of the best characters on Gilmore Girls). He and Rory also seemed to fit together like hand in glove. But even with their cutest moments and Jess’s better qualities, we can’t deny the fact that he was actually a huge jerk.
He did so many selfish and unforgivable things, but what’s more frustrating is the fact that he often got away with his behavior because of his charm. During their relationship, Rory had to put up with so much of his crap, and in the few times that she called him out, he never really owned up to his mistakes. He either shrugged it off or somehow turned the blame on her. This isn’t to say that her other boyfriends were a lot better than he was (Rory had the worst luck with guys, unfortunately). But if we had to pick the most inconsiderate, manipulative, and borderline abusive boyfriend of the group, then it would totally be Jess. Here’s why:
1. He Had A Temper Problem.
Jess was rarely ever in a good mood. He was always so angry and he was constantly on edge, ready to snap at anyone who rubbed him the wrong way or get into a fist fight if somebody offended him (including Rory’s ex, Dean). We totally get that he had a rough past, but that was no excuse for lashing out and projecting his anger onto innocent people. It only ever created even more drama.
2. He Rarely Ever Took Responsibility For His Actions.
As far as Jess was concerned, he could do whatever he felt like doing, regardless of the consequences. And if they turned out to be bad, he didn’t really care and it was almost never his fault. For instance, when he was flunking in school, he didn’t own up to the fact that it was because he kept skipping classes. He just figured that he didn’t need classes anyway because he was a genius and school was for losers.
3. He Tried To Pursue Rory, Even Though He Knew She Was Taken.
When he found out that Rory had a boyfriend, he didn’t do the respectful thing and back off. He only took that as a sign to try even harder to win her over. And how did he do it? Well, he belittled Dean every chance he got and then flirted with Rory as if she were single. Then, to top it all off, he intentionally showed up to a Stars Hollow dance with a date to make Rory jealous. Definitely uncalled for.
4. And When He Got Her, He Showed That He Couldn’T Care Less About Her Interests.
It never mattered that Rory really wanted Jess to take her to prom or join her for movie night with her mom. If he wasn’t interested, then he had no intention of doing it. No matter how important it was to Rory. The fact that he couldn’t care less about her hobbies and interests should’ve been a major red flag pretty early on. But hey, at least he still had his charm… right?
5. Yet He Always Expected Rory To Comply When It Came To His.
Though he didn’t show much interest Rory’s hobbies, he always expected her to jump at the opportunity to do whatever he wanted and he always expected her to be available. In one episode, he left Rory waiting for him for what felt like forever and showed up to not see her there. He got pretty angry, and poor Rory was forced change her plans and go to a hockey game instead. So when Jess showed up with concert tickets without offering a sincere apology… let’s just say we were too amused. But for ROry, just like that, all was well.
6. He Had No Respect For Rory’S Mom.
It’s like he didn’t even try. And the most frustrating part is that Rory practically begged him to be nice to Lorelai. But still, throughout his entire relationship with Rory, he didn’t show a single ounce of respect. Some of his comments were straight up rude, and his conversations with her usually felt forced and awkward. He made no attempt to change this. But if he had a conscience at all, or care for Rory, he would’ve at least had the decency to make an effort.
7. …Or For Luke.
Though they did have quite a few great bonding moments, the kid drove his poor uncle up the wall. Luke was so generous and he tried to be reasonable, but Jess maintained a sour attitude and showed so much disrespect – often times for no reason at all. He just came off as an annoying and ungrateful brat. But thankfully, they managed to find some common ground after Jess grew up and moved away. (FYI, that scene where Luke pushed him into the lake? Easily one of the top five scenes to ever air on the show.)
8. He Disrespected Literally Everyone, Basically.
He even told Rory this and admitted that he only liked her (which is actually extremely creepy and very unhealthy in a relationship… but we guess it’s hard to see that when you’re a lovesick teenager). He was so hostile and rude to everyone else, and it didn’t matter if they were perfect strangers or if they were Rory’s relatives. For example, remember that one time when Emily planned a dinner to meet Jess for the first time? He had the nerve to not just show up late, with a black eye no less, and then had too much pride to tell them that he was attacked by a goose. That would’ve been better than anything they were thinking!
9. He Seriously Sucked At Communicating.
Aside from the fact that he couldn’t hold a decent conversation (or any conversation, for that matter) over the phone, Jess never really communicated about his personal issues with Rory. For instance, he never told her about the fact that he couldn’t take her to prom because of his awful grades – and he never told her that he was failing in the first place. He also never mentioned that his reason for running off was to go see his father, which was kind of a huge deal. But see, good communication is a huge factor when it comes to successful relationships, so with this kind of behavior, he and Rory were basically doomed from the get-go.
10. And He Was So Whiny.
Jess complained about literally everything because he was always in such a bad mood and he hated everything. He didn’t like school, Stars Hollow, or even the people in Stars Hollow. And he never hesitated to remind Rory of this. Talk about annoying.
11. He Once Totaled Rory’S Car.
To be honest, Rory is partly to blame for this. After all, this never would’ve happened if she didn’t let Jess, an inexperienced driver, control her car. But anyway, this all went down when Jess tried to talk Rory out of tutoring him and suggested they get ice cream. She agreed, but then she asked Jess to get behind the wheel. Moments later, Jess crashed the car because he was too busy focusing on his ice cream (and Rory), leaving our girl with a broken arm. Did we also mention it was the car that Dean built for her?
As far as we know, Jess didn’t even offer to pay for the damages or fix her car …Of course not.
12. He Tried To Sexually Assault Rory.
If this doesn’t make Jess the worst boyfriend in the world, then we don’t know what does. He and Rory went to a house party in one episode, and he felt all moody and upset because he learned he couldn’t graduate. To get it off his mind, he started a makeout session with Rory while they were in a room. But then he came on way too strong after they ended up on the bed. Rory told him to stop and he still kept going — trying to unbuckle her be;t. It got to the point where she had to raise her voice and get away from him. Not cool.
13. Then Made Her Feel Like She Was In The Wrong For Trying To Stop Him.
So of course, Jess then got annoyed because he didn’t get his way. Even though Rory tried to explain that she didn’t want to lose her virginity to him that way, he started yelling at her for coming up to see him in the first place like it was her fault he couldn’t control himself because she was there. Rory actually left on the verge of tears. (And of course, a fight between Dean and Jess proceded over Rory’s honor.) Now tell us, does that sound like a good boyfriend to you?
14. He Was Emotionally Abusive.
If you really think about how Jess treated Rory throughout their relationship, you’d see that he was often cold, neglectful, and extremely inconsiderate of her feelings. It’s kind of disturbing to think about, considering the fact that he claimed she was the only person he liked. But whenever he was in the wrong, he always managed to manipulate Rory into thinking that it was somehow her fault. He ignored her a lot, and for some reason, whenever she tried to stand up for herself, he got irritated.
15. He Dropped The “L” Word At The Worst Possible Time.
When he finally returned to Stars Hollow, he popped back into Rory’s life and decided that declaring his love for her would automatically solve everything. But no amount of charm or “I love you”s could erase the fact that he was a total douchebag to her. Like, who runs off without warning, returns and then expects everything to be okay? Thankfully, Rory knew better than to fall for the grand gesture.
16. He Stormed In And Out Of Her Life… And Always Expected Her To Be Waiting For Him
Even before they were dating, Jess ups and leaves Stars Hollow after a fight with Luke. He comes back on the day of Sookie’s wedding and then plants a kiss on her — even though she’s still dating Dean. Then he finally gets her, just so he can leave (without saying goodbye) at the realization he’s not going to graduate from Star Hollow High. He comes back, says he loves her, leaves. Comes back again, asks her to run away with him, doesn’t take her ‘no’ for an answer, he leaves again. Honestly, I’m getting whiplash just thinking about it!
17. He Expected Her To Run Away With Him.
We’ve mentioned this, but it needs to be emphasized. He *literally* tried to talk Rory into leaving Yale and her family behind to go and run away with him. …Like, really?? After all that he put her through, did he really think that she’d throw away her Ivy League education to be with him? A guy who totally disrespected her family, dismissed her interests, and never even had the decency to say goodbye when he left? …PLEASE.