so i saw this misquoted post and went into an entire essay about the meaning of what jess is actually saying here and it got waaaaay too long to reasonably just post as a comment, so yeah.
i could be wrong, but i'm almost 100% certain that he actually says "the girls that i like don't give a damn about me". it's a small change, but one that i think is incredibly important and sent my brain into a tailspin needing to dissect my bby boy jess mariano
okok so obviously in this scene, jess is primarily talking about rory which is emphasized by the rest of this line where he calls out luke for waiting around for lorelai (though he doesn't directly mention her name, the audience knows)
however, in the line above, he didn't say girl he said girls which implies a pattern of jess liking girls who either don't like him back or don't want to like him back, even if they do (the latter being the case for rory)
not to go all 2012 tumblr with this, but it reminds me of we accept the love we think we deserve
so let's go back over what we know about jess
his dad walked out on him when he was a baby. a child could easily interpret that as them being undeserving of love
his mom was neglectful (and likely at least verbally abusive based on the way speaks to tj) and seemed to always put boyfriends/husbands above jess on her priorities. again, this would also likely be interpreted by a kid as being unworthy of love
then he got shipped off to a grumpy uncle and a town that hated his guts before he ever stepped foot off of the bus. sound like it could make his feel unworthy of love (though he was already unaccepting of it by this point)
then he meets rory and feels an instant connection with her and he doesn't really know what to do with that plus he's a teenager who has never had any real stability in his life, but he does start actually putting effort into his interactions with rory (the sleigh, the bid a basket, bringing food over, etc) and even furthers that when she asks for him to try to be nice to her mom.
it's almost like he's trying to make himself feel more worthy of love, but he is still a highly traumatized child, so he's less than perfect, but he does end up catching rory's interest
she then kisses him before running off to washington and not speaking to him for 3 months
all of that effort got pushed right back into his face which, you guessed it, put him right back into the place of feeling undeserving of love.
so he gets with shane and - according to jess - they treat each other like crap. we don't know much about shane, but it seems like she probably also had a background that made her feel like it was okay for jess to not care about her as long as she also showed she didn't care about him
however, we do see some minute level of care in the fact that jess chooses to break up with shane before getting together with rory. while this normally shouldn't be noteworthy, any instances of not choosing to cheat when you could cheat in gilmore girls is kind of a big thing
so at this point, rory and jess are finally together and, unsurprisingly, jess fucks things up. not to say that rory was a perfect girlfriend, but more on that later. jess is 100% the reason that their break-up happens in the way that it happens (though i do believe a break-up was inevitable even if everything had gone to plan)
jess, who has never been shown proper love, doesn't know how to be in a proper relationship, but we do see him making effort. he doesn't want to go to friday night dinner, but he does. lorelai tells him off for not calling rory (even though if you rewatch that episode, the promise to call wasn't a set in stone thing, more of a way to end the conversation bc lorelai interrupted them), he takes her out to see the distillers and then we see them talking about hanging out and watching movies 3 nights in a row. he may not have known exactly what to do or say all of the time, but the boy was genuinely trying
and then the world collapsed around him and he went with one of the only survival tools in his belt, running.
he tried to make himself what he would view as worthy of love, he tried to give rory proper love back, but he was never given any new tools for what to do when things go south. if he had had therapy (which should have been required given his circumstances) he could have learned better ways to handle the floor falling out from under him, but he didn't. he put in a ton of effort, but without the help of a better toolbox, the trauma response kicked in
so he finally tried to accept love that he likely felt unworthy of, just for the world to laugh in his face for having the audacity to try to escape the cruel fate of a seemingly loveless childhood
obviously jess comes back a few times, but i'd rather tackle those from rory's side but still with respect to good ol' chbosky's we accept the love we think we deserve
so rory and jess are two sides of the same coin when it comes to their background. they were both raised by single mothers and had absent fathers. the difference is that lorelai always put rory and her needs above all else while liz seemingly didn't.
rory never had to know what not being loved felt like. being loved is her default. and i am not in anyway admonishing lorelai for doing that, i respect the hell out of her for always always always putting rory first, but between her, her grandparents, and the either town of stars hollow, love became being put on a pedestal. the problem with that is that rory is a human being in the human world who is interacting with other humans. but the expectations ingrained in her are unachievable. this is not to say that expecting someone to treat you well is too high of an expectation, but when doing that from a pedestal, the ones who put you up there will never accept anything other than their own expectations
we first see this with dean. at first, lorelai hates him, but once she sees him as the nice guy who changes out the water bottle and ethically gets rid of spiders, she gains a far more positive view of him
so when the first rory and dean break-up happens, lorelai and the town turns on dean for not living up to the expectations that they had for his and rory's relationship
then lorelai finds out about the reason for the break-up, and rather than trying to help rory through her feelings and to navigate what it is that she wants, she just tells rory to not be afraid of love. this tells rory that love is a guy like dean. it doesn't matter if she feels love, it doesn't matter what her perspective of the relationship is and whether she feels like she loves him or not, no. it's that from lorelai's pov, he was a nice guy who loved rory and treated her well (again, just from lorelai's pov, bc she doesn't see the side of dean that is incredibly controlling and gross)
so to rory, love is the guy who calls (even if it's 20 something times in like a 3 or 4 hour period bc why tf does no one ever talk about that scene?? and how did lorelai not get a major fucking ick from it??? idek man), the guy who helps her mom out around the house
her feelings in love don't matter, what she gains from love is what matters.
but then jess comes around and she tries not to be around him too much, but when she is around him, there's an undeniable spark (like the picnic basket to pizza to bookstore shopping pipeline). the problem is, he's nothing like dean
he's nothing like who she has been told embodies love and that scares her to the point that she denies her feelings for jess for a long time, misses her mother's graduation because she chose to go see jess, cheats on dean by kissing jess, hurts jess by running off and not talking to him for moths, and then she's pissed when she gets back and he's not just waiting for her like dean would have done
she's never taught what love should feel like, only what it should look like to people outside of the relationship
so even though she clearly wants something more with jess, she refuses to break things off with dean bc dean = love and jess = bad news
again, her actual feelings don't matter at this point bc of the love she's been told to accept isn't necessarily what love seems to feel like for her
but obviously rory and jess do eventually get together and she immediately starts comparing him to dean (which is why i mentioned earlier that rory was not a perfect girlfriend). she is able to accept that the relationship is different in some ways (like the fact that she and jess actually have stuff in common and it also seems like there was more of a physical desire there than we ever saw with dean ((ex. rory and dean never getting a horizontal kissing scene until it's time to for the affair vs rory and jess having one very early on in their relationship, rory talking to lorelai about potentially sleeping with jess when she never had that thought process with dean))).
so it seems like she was finally having the feelings of love, but because his actions didn't match what dean would have been, she feels insecure. and that insecurity is exacerbated by lorelai also always comparing jess to dean
and then the friday night dinner, jess shows up late with a black eye. rather than her trying to listen with empathy and trying to understand the circumstances behind the situation, she freaks out because it's not what dean would have done AND it goes against everything emily would expect of the guy rory is with.
so, again, rory's view on a relationship is more based on how others perceive the relationship rather than her own feelings of her relationship. but she's also just a teenage girl who is doing what she's been taught to do: rely on others expectations rather than her own feelings
and we see time and time again, that anytime her relationship doesn't live up to the expectations of those around her, she bottles it up and refuses to try to have an actual honest and open conversation about her feelings and what she needs out of her relationship
jess only even finds out rory is upset with him because lorelai tells him. and, as mentioned earlier, once he knows, he makes a much bigger effort to be what rory deserves
then obviously everything goes south and rory ends up with her heart broken, but it also seems like she doesn't feel like she can open up to anyone about the heartbreak without hearing a million i told you sos because no one ever thought jess was good enough for her, so she has to squash that pain down, but we definitely see it throughout s4 esp considering it's the only season of the entire show that rory is single the entire time
she put herself out there for someone she was told was less than her and it slapped her in the face. and jess comes back and tells her that he loves her and then again to ask her to run away with him, but she's already been burnt from trusting a love that others told her was beneath her and she's not in a place to take that chance again
so what does she do? she runs to dean even though he's married. she was always told he was what she deserved, so maybe she could erase the pain from taking a chance on someone who wasn't in a place to be able to handle life like an adult (bc he wasn't an adult, SHOCKER!!) so she sought refuge in who she was told was right for her
and then everyone (rightfully) judged her for it. and she tried to stick it out with dean bc he was supposed to be the perfect one. even when we see in s5 where things are so clearly not working out between the two of them, she once again refuses to break anything off bc of the messages that she's received her entire life. he does eventually break things off with her again, but this time it seems a little less dramatic than their previous ones bc suddenly stars hollow isn't rory's main tie anymore, now it's yale and the world of her grandparents.
which brings us to logan.
dean is to lorelai as logan is to richard and emily
rory is fully integrated into yale by s5 when she meets logan. he represents the world of her grandparents and their expectations for her and what kind of love she should receive.
it should be one based on family name and earning potential. and it helps that logan is also attractive
so with rory spending exponentially more time in her grandparents world than she ever had before, she starts to take on their expectations for what she should be looking for
it shouldn't matter if logan is gone all the time, bc richard is gone on business trips all the time
it shouldn't matter if she is able to realize her dream of being a journalist bc emily is a stay at home wife who manages their social calendar and the employees who work in their home
it shouldn't matter if she even graduates as long as she gets a MRS with a blue blood
logan doesn't know rory's birthday, but no big deal bc richard is constantly forgetting about events emily has told him about
logan got her a birkin bag!! something she didn't even know what it was or the value of it, but emily is jealous so it must be a good gift even if it doesn't actually mean anything to rory
logan cheated on her with all of honor's bridemaids?? it's merely a small thing to overcome just like richard metting pennilynn lott monthly for decades without telling emily about it. they worked through it, so that's gotta be love, right?
and as rory falls deeper and deeper into a world that she's naturally great at fitting into, logan doesn't even notice or care to notice how she's drowning in living up to the expectations of her grandparents vs the expectations of her mother vs her expectations of herself
and she's still never been taught to talk through feelings, so she just continually sabotages herself and logan doesn't give a fuck about it until suddenly rory's ex is back in the picture
and what do we see of jess in his s6 return(s)? we see a more grown up jess who took all of his broken pieces and tried to turn them into somebody that he's proud to be, though he doesn't wear it with arrogance
obviously we see very very little of his life, but it seems like he has finally found that the most important person to love him has to be himself. he tried to fix himself for rory and it didn't work. but he fixed himself for himself and he's suddenly achieving dreams he didn't even know he was worthy of having to begin with
however, rory is now the one in the situation where she isn't loving herself or taking care of her own wants and needs enough to be able to accept the love that she truly deserves, because she's never been given those tools
and i'm not saying that rory didn't love logan, but it does feel very much like she was expected to love logan. and after the philly visit when she might have finally been reconsidering what she wants love to look like in her life, logan nearly dies and she has to put her own wants and needs on the backburner for him
she has to make herself small while he heals
and then s7 doesn't even matter bc asp left and the show gave logan a complete personality switch where he suddenly gave a shit about things other than getting wasted and having fun with the ldb
and then in ayitl we still see rory constantly self-sabotaging until jess, who was never supposed to be good enough for her, gives her the nudge she needs to take a more proactive role in her own life (for the second time)
idek what all of this means, but it's just so interesting that neither of them were ever taught what love should actually be, but jess is given the room to grow and discover at least some level of self love, while rory, ever the gifted and talented kid, keeps getting stuck in the cycle of other peoples expectations vs her own
which makes writing her book even though lorelai wasn't thrilled about it all the more impactful and it was something she wouldn't have done had she not talked to the guy who everyone else always villainized and learned that expectations are not actually reality