so, going through the dairena tag, I have to say that I really think that their dynamic is so instrumental in understanding each of the three characters. they really are all tied together through their love for each other.
they really are, it's so...blair and serena knit their souls together when they were children, and it just shapes....everything
dan's entrace into their world is his love for serena, which begins at a faroff look at a party, where he sees BOTH OF THEM. TOGETHER. but he begins to really fall after he really sees her. after witnessing the photoshoot and the fight of 1x04, the first time he and Blair really connect. he learns to see the both of them, Serena and Blair, as real people with real flaws and real virtues. it's Serena as a whole he falls for, but he doesn't until after he sees her best friend as a whole person too.
Serena falls for Dan after coming back to NY after doing the wrost thing she could do to Blair. She promises herself to stay away from Nate completely out of love for Blair, and in concurrence with that choice, she finds Dan.
Blair is forced to reckon with Dan when her best friend Serena sets her sights on him, and then he's always just, around. but he gives decent advice, and Serena is happy. happy in a way that Blair can't remember seeing before, which makes her jealous, both of Serena and of Dan. that Serena can be happy and that Dan can make her so. And then, when Serena shows up at her door broken and scared, and then Dan comes looking for her, Blair breaks his heart. because she loves Serena, and Serena won't see him.
and years later, when Serena breaks again, and Blair has to be the one to fix it, she knows that the only person who cares as much as she does is Dan, so she goes to him. "You love Serena, don't you? Then we have that in common."
and then Blair and Dan find points of connection that arent' Serena, but she's always there. she's an indelible part of each of their hearts, even after they fall in love with each other.
but when it looks like they could be something, Blair backs away, parly because of her own fear of what they're becoming, but mostly, she loves Serena. and Serena is hurt by this, so there's no way Blair can pursue it. so she pursues Louis instead.
eventually blair and dan's gravity is too much for them to hold back anymore (not that dan ever really tried that hard), and serena is made to see what they mean to each other, and because she loves them, she has to give them their chance, since blair tried to give her so many
I could go on, but you're so right, every choice they make regarding each other is wrapped up in the other person. they're so intrinsically connected.
i think robby vs frank's sexism is so interesting and i know its def a point that has been made before, but robby's sexism isnt obviously presented as such but you clearly see it in the way the show often frames the woman as being hysterical and unreasonable (i think this is more a fault of the writing but) and robby talks to the man in a given pairing in order to ~sort things out~, or how he doesn't take david's threats seriously meanwhile dr mckay pulls him aside many times to try and underscore the severity of the situation, and points out that robby is clearly prioritizing david's feelings/life/experience compared to any harm he might inflict on the girls on his list. despite this his character usually comes off very empathetic, well-intentioned, etc which makes it hard to pin down that he an obviously misogynistic character.
meanwhile frank's sexism isn't subtle and is pointed out when it happens. both times he tries to diminish abby's work as a (presumably) stay at home mother with 2 kids under 4, and clearly doesnt think abby's work is as hard as his ("im a doctor"), dana comes back at him right away. it also fits in with the initial impression of his character, which is a little uncaring, a little more abrasive, a little more dismissive, etc than robby (i dont mean to say frank is uncaring, i just think this is an easy impression if compared to, say, robby. but i also just think the way frank cares looks different.)
i also think its worthwhile to note that robby's strongest connections in the pitt are frank (star resident until he isnt), abbott, previously adamson, and then when it comes to the newbies it would probs be whitaker. meanwhile, frank's strongest relationships i would say are mel (obviously), and then close, playful relationships with dana, collins, and garcia. there obvi are exceptions, like frank looks up to robby a lot and think they're friends, and robby Was close to collins but they now have a tenuous relationship. but i think its interesting to pay attention to this.
Taylor is like... weird when it comes to ending relationships. Per The Bolter she has the habit of running head first Fearless from her relationships (whether that be solo or not) even back to the Drew of it all (Mr. Midnight Rain himself).
She had dreams she had to pursue. He had a simple life he wanted to live and was perfectly suited for. They broke up because they were heading in different directions (literally. Man was fully moving away for college) but she seems to feel as if like, she was at fault because she wanted to pursue a career in music and had she not they would've "worked out" (just ignore that had she not wanted to be a musician she wouldn't have moved to Hendersonville, and they wouldn't have met😭).
Then you've got the Taylor situation where she not only ditches him for being nice but (mainly), for someone else entirely. Then Matty 1.0 who she... ditched. Then Calvin who she ditched both for someone else and because he was "holding her back" ala Drew. Then Tom who she again ditched, specifically for someone else (also cause he's weird). Then Joe who she... ditched both for someone else and because the trajetory and pace of their relationship was no longer meeting her personal goals (and because he wasn't equipped to handle the New Heights of her career's trajectory). Which then leads to Matty who... ditched her, which I think highlights another key pattern in her discography - her deepest heartbreaks come from two scenarios: when she HAD to bolt, and when the other person beat her to it (or worse, both!)
Sam Sam Sam cheated, leaving her no choice but to bolt. In turn he got like 90% of the Fearless breakup songs. Joe J just dipped, leading her to drag his name through the mud. John seemingly just like... got bored and stop calling (effectively bolting), which evidently gave her the clarity to realise she needed to bolt (not pick up his calls when they eventually started coming back through).
Jake was so flippy-floppy that despite him being the one to "bolt" initially, she was the one who had to tell him to keep running and also run herself (interesting parallel between "running scared" and "the bravest thing I ever did was run"). Harry was back and forth, but it seems like HE was the one to "end things" (though like Jake he did come crawling back). And with Matty, she has the guilt of leaving him the first time, and then the betrayal of him leaving HER the second time, after she fucked up her life for him😭😭
This got VERY ranty. My apologies for that. Anyway, in conclusion, girl is MESSY, and it makes her simultaneously endearing and frustrating.
THE GIRL IS SO MESSY AND THIS IS VERY ON POINT THO. You know your lore lol. You do know your lore.
I feel like it’s not a stretch to say that Dair’s previous relationships/sexual partners paralleled each other in one way or another (this got long so added a read more):
DAIR APPRECIATION WEEK 2021 DAY ONE: Why do you love Dan and Blair?
I broke down what I love about Dan and Blair into five parts under a read more below. The tldr is: their compatibility, their parallel arcs, their slow burn, the larger message it would've given GG if they were endgame, and finally their mature, adult relationship (aka "pure and simple love").
Warning: I basically wrote a fucking essay lmao. Cited my sources and everything.
I. Compatibility
Dan and Blair have great chemistry sure, but they have something that I don't think any other pairing on the show really had: common interests. They were pseudo-intellectuals who could talk about books, literature, art, etc. with each other ("Dan and I have a real connection. We did things like visit the Dia and debate Charbol versus Rohmer..."). And I know in TV world all anyone cares about is chemistry, but in the real world the key to a long lasting relationship is common interests.
And yet they are also still an opposite attracts pairing, just in the best way, where they are opposite in personality and background, but still share lots of common interests. Blair was the rich mean girl from the Upper East Side and Dan the "poor" loser from Brooklyn, but they still can relate to one another, they can still find stuff to talk about together, they still come to enjoy each other's presence and friendship.
And back to their chemistry: it isn't steamy chemistry 100% all the time (although they can certainly go there). Their's is a sweet chemistry, a chemistry where it's clear that they respect each other, that they know each other on a deep level, that they understand each other more than anyone else. It's a chemistry that you believe could lead to a satisfying marriage one day.
And I know I've said this before, but to me Dan and Blair are just soulmates.
II. Parallel Arcs
I am such a sucker for when two characters' life journeys parallel one another and Dair had that in spades. In season 1 especially, they were both dealing with the abandonment of a parent (Dan's mom/Blair's dad), they both lost their virginities and entered into sexual relationships with much more experienced partners (Serena & Chuck), and they both had their sights set on one school (Yale & Dartmouth - although come season 2 this became Yale for Dan, giving them even more in common).
I've also already talked on here about how you can parallel all of their other romantic/sexual relationships to one another, as well as how they both were abandoned by their best friends sophomore year. And, they both have a bad habit of going back to the same person over and over again (again, Serena & Chuck).
To me, Dan and Blair are almost narrative foils. Dan's relationship with his father starts out pretty solid but deteriorates over time - Blair's relationship with her mother is the exact opposite. Dan pines, while Blair loves to live in denial. Blair sees her life as a movie, Dan sees his life as a novel.
And that makes it all the more satisfying to see them come together, to learn to appreciate their differences, to accept their similarities, to see them grow together (albeit briefly) over seasons 4 and 5.
III. Slow Burn
A lot of people on here use this word incorrectly. If the characters kiss during season 1 (unless it’s under false pretenses) it’s not a slow burn! But Dan and Blair are a true slow burn (whether or not that was intentional).
From that hallway scene in 1x04, it's clear that Dan and Blair have a deeper connection and understanding of each other than they are letting on. We get brief glimpses into that in 1x15, 2x08, 3x18, and 3x22. All of that very slow build up makes it all the more satisfying when they become friends in season 4.
I truly think the W arc is the best written arc of the entire show. You very slowly see them accept their common interests, grow to begrudgingly respect one another, even begin to accept that there might be an attraction there. It never feels rushed, when they kiss in 4x17, it's earned (I use this word a lot - buckle in).
And then, yeah, the Louis arc was fucky (I stand by that they should've kept the love triangle Dan vs. Chuck, or Dan vs. Louis, all three was too much). But Dan standing by Blair through everything she went through that season was beautiful, to see her depend on Dan in her darkest moments, to see her realize that he's the one who will always be there for her...it just really, really worked.
And so that moment when Blair finally calls him "Dan" to his face, when it becomes clear they are finally going to be together...it's one of the single most satisfying moments in the entire show. Because, again, it was earned.
IV. Larger Message
As this video essay posits, the showrunners were left with a choice after the 2008 economic recession: "Either adjust to the times or lean further into an escapist fantasy where extreme wealth is the status quo...and lean they did. For the sake of providing their audience with an escape, the dark underbelly of extreme affluence became the show's core theme. The more it began to sell cynical opulence as standard escapism, the more the writers and fans turned on the less wealthy characters."
Furthermore, by revealing Dan as Gossip Girl, "It transitions him from pretentious soft boy to borderline sociopath, actively ruining the lives of his friends, family, and crush just to get a foothold in Upper East Side society. And then the show did something it had seldom deemed to do for a less wealthy character: it rewarded him...And thus, the show presented us with the most insidious message of all: wealth, privilege, and power corrupt...and that's okay."
By having Chuck & Blair and Dan & Serena as endgame, GG became one of the most cynical shows on the planet, where (to quote Constance Grady) "all relationships are transactional".
But yet: "The sole bright spot in the midst of this cold universe in which relationships are bought and sold like real estate came in the form of Blair’s brief season four romance with Dan...it marked the last hurrah of the first version of Gossip Girl: In a world in which money is so powerful that it makes romantic relationships indistinguishable from prostitution, Dan and Blair were working to create an authentic, meaningful bond outside of the influence of wealth and privilege."
If Dan and Blair had been endgame (and Dan hadn't been GG - although we all know that one is bullshit anyway), it would've been a rebuke to that ideology, it would've shown that there is more to a good marriage than a shared tax bracket, that a genuine connection is more important than wealth and privilege. That abuse does not equal love.
But alas, that was not the story they wanted to tell I guess.
V. Mature, Adult Relationship (aka "Pure & Simple Love")
I am personally not much of a fan of grand romantic gestures. I often find them shallow, childish, and showy. To me, it is far more romantic for Dan to have secretly written a book about Blair, for Blair to submit Dan's article to Vanity Fair, for Dan to say "it wouldn't to me" when Blair asks if it would matter if she was pregnant with another man's child (especially since this moment is (take a shot here), you guessed it, earned - we know he's being honest because we already saw him do this with Milo).
Now, I am personally not as much of a fan of the Met Steps moment as everyone else (Blair's desire to be royalty is probably the thing I like least about her), but that was probably Dan's grandest romantic gesture and yet...it's still so simple. It's really just a plastic tiara and a cab ride. Which is what makes it so beautiful. Because it's not about the money or the extravagance or showing off to anyone else...it's about Dan showing Blair he truly knows her. And to me, that's the healthiest way to do a romantic gesture.
I also love their bad sex arc in 5x18 because a) it's real - most real world couples don't have earth shattering sex the first time together, it takes time to learn what your partner likes and needs and b) because they actually (after getting drunk at Dorota's & Nate's) communicate about it and work out their problem like adults.
Because that's the thing about Dan and Blair - it's a real adult relationship. It's not a never-ending game of cat and mouse, it's not a fallback, it's not a bad habit...everything else just melts away when they're together. They grew and changed together...they learned to put aside their prejudices and see each other beyond their facades. They became better people together. They always had someone they knew they could turn to.
warning : my take on the characters. i haven’t watched the show in a while, and might be remembering them the way i want to, not to mention my bias because the humphrey siblings are my favourite characters, especially jenny, who i have become increasingly defensive of.
i think it’s interesting that alot of the people that have had significant impacts on dan and jenny’s lives are women and men respectively. with dan, it’s his mother, serena, blair, vanessa, jenny, even georgina, lily, the list goes on. with jenny, it’s rufus, eric, dan, nate, chuck, damien, etc. i wonder if it ties into their respective problems with their parents. as we see throughout the show, dan is clearly much closer to rufus than he is to their mother, whose leaving he still suffers consequences from. while i don’t doubt jenny deals with these same issues (albeit in vastly different ways), it seems she is much closer to their mother, whereas as we see she and rufus almost never seem to be on the same wavelength.
dan, as a result of much of his anger/disappointment over his mother leaving, clearly has abandonment issues, he “clings” to those in his life, he would do anything to make them stay (i still think his relationship with vanessa just being left like that is incredibly ooc but oh well, the writers aren’t exactly good at their job so), i think most significantly shown in his relationship with serena, blair and georgina (yes, georgina). with serena, as i’ve mentioned in a different post, he clings to the girl he once knew, to the girl he fell in love with, because he wants things to be as they once were (at least with her), if he doesn’t have her, what does he have left? (at this point, she really is all he has left, because he has fallen out with everyone else in his life) with blair, he is insecure, afraid she will leave him for chuck (which, ultimately, she does), so he gives her an “ultimatum”, me or him, he tells her he loves her in an attempt to make her stay (of course, this is likely not the only reason why he tells her, as we’ve all seen, dan really does love her, so it isn’t something he was just saying). with georgina, dan knows what he’s getting himself into. whether he ever had genuine feelings for her is a whole other conversation, but he knows how things will end with her. they both get what they want, and no one gets hurt.
jenny strives for control. much of her loss of control (or, never having much of it in the first place) is in part due to men in her life : rufus and chuck. of course, we should keep in mind she is only 14 at the start of the series, so it makes sense that she wouldn’t have the freedom her father offers to dan, who is 17 (or 16 i’m not 100% sure). however, we do see that at no point in the series, even when she’s older, does she ever get the same treatment her brother does. where she ultimately loses all her control (or feels like she does) is when she is first sexually assaulted by chuck. jenny doesn’t encounter this once, but three times. the second when she is left drugged at a party (or was it drunk i’m not entirely sure forgive me i’m not fact-checking lol) by someone she considers a friend intending for her to get raped, the third when she loses her virginity to chuck, the person that had assaulted her all those years ago, an interaction that at best has dubious consent (and at worst, which i think is the correct interpretation, is rape). coincidentally (or maybe not), in all three occurrences she is “saved” by men, dan (&serena), nate, dan and eric, respectively. [there are many great reads on the internet about jenny’s arc and her strive for control over her life after the first assault, but i won’t link them because there are too many, and some have controversial takes that i don’t agree with so]. now, this could be just the writers letting their misogyny show through, which would not surprise me because they do this on more than one account, it could also be really, jenny does not have very many women in her life. that’s not to say there are none, or that there are none that have had significant impacts on her life, i just think the men have been much more signifant in her life, since much of her arc and growth involves the males in her life, the women all being mere passersby (lily, who tries her best to be the mother jenny never had, her biological mother, who while she is close to, has made the active decision to not be in her children’s lives, serena, who also tries to be a sister to jenny, blair, who punishes jenny time and time again (it will be said, that blair has a lot of unaddressed internalised misogyny), agnes, who jenny genuinely believes to be her friend and betrays her more than once, vanessa as well, who jenny has seen as a friend and sister, betrays jenny by taking away the one thing she has been clinging onto, the one person that is safety and security to her - nate)
that’s to say, something they have in common is when they feel abandoned both will do anything to get things or people back. where they differ, i think, is dan will hurt the people that leave him, whether that is with his words or actions. jenny does the same on a few occasions, but mostly she lashes out at third parties or at herself when she feels hurt. note that a lot of the way they feel and the actions they take as a result is also influenced by their ages and levels of maturity, because even when jenny leaves, she is only the age that dan is at the start, so there’s quite a difference there.
i doubt it was deliberate because once again, the writers aren’t exactly the brightest, nor do they care enough about characters that aren’t chip whiskers to bother with the humphreys, but i like thinking too much about everything so
As a Taylor Swift expert, Gaylor hater, and recovering 1989er, you probably don't want to know that apparently in the notes of the re-recording Taylor Swift talks about how she wasn't dating any of her female friends, and the Gaylors are having meltdowns on twitter. Words like "gaslit" and "queerbaiting" are being used.
of COURSE I want to know about that, I need to go log back into my twitter account RIGHT NOW
also goddddd as a certified 1989 enjoyer I'm gonna have to listen to Taylor's Version :/
You are so right about Serena but can we talk about Jenny. I understand why people hate her but I always thought she was funny and had so much potential to be an interesting foil to dan. It still infuriates me that in the first ep they have Chuck try to assault her and in her last appearance as a series regular he sleeps with her (while she's like 16) and then acts like it's her fault he and blaire aren't together. I like to think after she left she got to be the main character and had a bunch of London girlfriends
oh jenny is literally my favourite gg character and i will die defending her. the way both the fandom and the show treated her was absolutely horrendous because jenny was arguably the Best Person out of the entire main cast (second maybe to vanessa, because the way they wrote her out with that juliet/serena plot was so insanely ooc and just a way for the writers to throw the poor black woman under the bus to prop up the rich white kids) and yet she was repeatedly demonised by the writers, the fans, and the other characters.
the thing about jenny humphrey is that she made a lot of mistakes and did a lot of things wrong but she was punished far more than the ~njbc~ (hell dynamic) and even her brother ever were. jenny learned very quickly that if she wanted to survive in the world of the upper east side then she needed to learn how to play their games, and then she was hated for doing exactly that. chuck committed abuse and sexual assault and was forgiven by the audience, the writers, AND the characters (because even pre-blair, the way blair, nate, and to a lesser extent, serena, suggest that what chuck did to jenny was not a One Off and they were all just willing to look the other way). but jenny loses her best friend, her family berates her, and she's banished from the city she's lived in her whole life because of something that wasn't...really her fault. given jenny's mental state at the end of s3 and chuck's previous behaviour towards her, i do think there's a lot of ambiguity around how much jenny could Consent, especially that she regrets it immediately after (and not just because of the blair of it all).
blair's treatment of jenny also becomes grosser and grosser to me with each rewatch, because jenny did not deserve how cruel blair was to her, again and again. you could argue that jenny got her own back in the back half of s1, but her actions were a result of spending months being demeaned by blair, and basically acting as a servant for this girl she just wanted to befriend. blair is the reason behind a lot of jenny's ~corruption~, and yet blair is the one who hates jenny the most for it. and the show wants us to root for blair even in her cruelest moments, whereas jenny is seen as nothing more than a calculating bitch.
i think people would like jenny more if she just learned to stay in her place, be docile for blair, and recognise her ~inferiority~ because she wasn't born into generational wealth. sure, dan's shunned for the first few seasons, but the characters are a lot more open to him because dan rarely pushes back. jenny always does, because jenny is smart and determined and capable and refuses to spend her life being a doormat. jenny knows that power comes with a price, and she's willing to fight for it, but unlike the others, jenny isn't allowed to lose. not only because she isn't able to bounce back like blair or chuck or nate or serena, but because it's a lot harder for jenny to live with the things that she's done. serena, nate, and to a lesser extent blair and chuck, do feel remorse at times, but jenny doesn't know how to cope with the consequences of her actions. and i don't think it makes her a bad person, i think it makes her so tragic, because she's willing to play the game, but gets so caught up in it that she forgets that the rules are rigged against her. and so she loses, and the people in her life can't forgive her, but she also can't forgive herself.
and the way she's written off is so infuriating, because it does demonise jenny, who was a seventeen year old girl struggling with so many demons. in season two, she was briefly homeless, had her work ruined by someone she considered a friend, and was so badly bullied that she stopped going to school (that throwaway line about someone trying to set her hair on fire in class...what!!!) she's already in a bad place when s3 kicks off and everything that happens just sends her on this downward spiral, because she has to play the game to survive but doing it is killing her from the inside out. and nobody except nate notices or cares, and so she latches onto him and crosses the line, but of course she'd be drawn to him. everyone else in her life was either taking advantage of her, openly hating her, or ignoring her.
jenny was pushed and pushed to her breaking point and then she was demonised for finally losing it.
something that's really telling about the way the show viewed jenny is how she's just...never brought up in the context of the dan and blair dynamic. which could be my bias talking but also. dan was so overprotective of jenny in the early seasons, and even though he forgot he was a brother for the majority of s3, he's the one that recognises the chuck/jenny situation for what it is (this begins and ends with chuck.) dan knows better than anyone just how much blair tormented jenny, and yet he's somehow...willing to forget all of that once he starts getting to know blair better? i know dan can be short sighted and he hates confrontation, but he does think that people should take accountability for the things they've done, and yet never expects blair to own up to and apologise for how she treated jenny. just....insanely ooc and proof that the writers didn't think jenny's feelings mattered, and basically wanted her gone from existence.
(which is also why they allow chuck and dan to have that weird semi friendship in early s5).
all jenny ever wanted was to be accepted and loved and wanted and respected, and the characters, the narrative, and the fans punished her because she was willing to fight for those things.
for the Character Asks, how about I give you your pick of any/all of our 3 established Gossip Girl Main Characters bc we're writing a whole show about these 3 rich dysfunctional gays lmao
hello YES! i enjoy our rich disaster gay trio sitcom (/dramedy) headcanon chats! work with for the other two so it would largely be headcanons anyway. i decided to go with jenny since the others don't have much canon to work with.
How I feel about this character: my beloved <3 more seriously, she's the character in gossip girl i find most interesting so this is going to be. long. anyway. she can be flawed and self-righteous and self-destructive and petty and she can be awfully, egregiously cruel, she knows how to take someone's insecurities or mistakes and hit them where it already hurts -- and despite all that, she's so sympathetic. because she's also ambitious and creative and starts off the show so optimistic and relatively happy-go-lucky, even with her parents' separation. she's cutthroat because she HAS to be, because she would never be able to hang in the upper east side if she wasn't, and that's the path she sees towards her dreams and doesn't she deserve her dreams? she knows she can hack it if she can just GET THROUGH THE DOOR. she's funny and charming and witty and SAD, sadder than i think anyone in the show realizes until she's imploded by the end of season three. she develops this armor of black clothes and sharp eyeliner and bitchy witticisms in season two and season three even moreso and so many people see this as character derailment or think it makes her awful or irredeemable somehow but i look at her and see a girl who's been tread on too many times, with chuck and with damien and with agnes and the guys in the club and what they almost did. with her father, even, and his lack of ability or willingness to understand where she's coming from, that she's not just sad or lonely at school, she's in DANGER. (evidence: the reference to the fact that apparently everyone except two girls in her chem class apparently tried to light her hair on fire?) so she builds up walls and she isolates and she makes decisions that maybe aren't great but she doesn't have the support she needs and all of this makes me feel so soft and sad for her and protective OF her and protective, even, of her right to be flawed, of her right to make mistakes. every other character in the show has equally (or even worse) egregious flaws that get excused or hand-waved by not only the fandom, by the narrative. jenny is held to a much different standard. the narrative screws her and casts her aside (and yes, i get that taylor momsen wanted to leave, i respect it, and i even respect that it's a teen drama and her exit was always going to be a little dramatic, but they did not have to do what they did) and if they didn't think all of this was the perfect storm for me to emotionally adopt her into the list of blorbos in constant rotation in my head-oven well. they've got another thing coming. tldr; jenny is the Born To Die trope except it's more like Metaphysical Innocence Born To Be "Corrupted". it's so clear what they're doing even in the pilot. i will go to my grave defending her.
All the people I ship romantically with this character: jenny x therapy LMAO. actually answer is uhhh idk. might be easier to give a list of my DEFINITE NOTPS (easily guessable, i'd assume.) i simultaneously DO headcanon jenny as having had a crush on blair and think they have interesting dynamic (and lots of angst and turmoil and admiration/jealousy psuedo-political warfare that makes me understand why people DO ship it) while also not really wanting it be like. A Thing. (i also think their relationship was too fraught and blair in particular was too awful to jenny for them to ever have a healthy romantic relationship, so.) i have... a soft spot for nate and jenny let's say? i don't think canon was the right time for them to be together, obviously, and i can easily see how some of her feelings could come across as comphet (especially with him being so constantly unavailable). at the same time, i think they have a lot of sweet moments that are rooted in like, affection and genuinely liking who the other person is. he's very gentle with her and i think jenny could have used a lot more gentle moments in the show. at the same time, i'm not sure they're ultimately the right fit for each other, and i don't really imagine that they're "end game", so to speak, but i do like reading the occasional post-canon fic about them. so that's where i land on them, i supposed. in actuality, i think jenny probably realizes she's queer in some capacity eventually, but that's a whole other question lmao.
My non-romantic OTP for this character: jenny and eric! but also jenny and dan! but also jenny and serena!! it's hard to pick lmao. i think the show does a pretty decent job showing the complexities of the friendship between jenny and eric given eric's limited screentime lmao. i think they hit something very grounded and real with eric and jenny's back and forth, which how much they love and need each other and also can't stand each other half the time, how their introduction was a really simple moment of jenny showing him compassion and him meeting her back with that effort full-force, with how they both value each other more than is common in heterosexual romance-based western cultures but also can't or won't or don't know that they need to or how to admit that to one another. it's a very honest depiction of a friendship at this age and of this kind, at least for me.
i was about to say that my feelings about dan and jenny are simpler, but i don't know if that's true? i might be repeating myself here, but if there's one thing gossip girl does well, it's grounded and realistic dynamics. they tease each other lightly and they tease each other too harshly sometimes, they fight, and they try to understand each other but often can't, they secret-keep for each other until that's no longer viable, and they do their best to protect one another and it's all just so balanced. one scene that stands out to me is when jenny steals the dress in season one and dan goes into talk to her and it's so clear he's had to take on somewhat of a parental role with her since their mom has been gone? and i'm sure that's frustrating for both jenny and for dan. but despite taking on this role of care, he doesn't treat her condescendingly or with any ire, he tries to be understanding and careful and thoughtful where rufus couldn't be. and while i'd say the show does a disservice to their relationship as time wears on, i think when dan gets the CHANCE to be a good big brother to her, he always always is. he tries to do right by her and even in her harsher, more isolating days, she still tries to trust him and lets herself be jenny around him moreso than she knows how to do with other people.
with jenny and serena -- i think i love what their dynamic could have been more than what it was? watching the pilot for the first time, i was sure there were going to be more big sisterly moments between them, but they end up going for conflict instead. which is understandable; like i said, it IS a drama. but serena tries so hard to be kind to jenny in the first season and while jenny wants to BE blair, i think serena's kindness lets her hold onto her dream a little longer, imagine that there's a world where she gets in with the in-crowd and someone like serena is there to back her up. i also think there's a really intriguing theme of jenny's arc paralleling what's serena's been through in terms of assault and sexual exploitation. the "the sixteen year old virgin" really exemplifies how serena WANTS to protect jenny from going down a path of self-destruction that could lead to her getting hurt even more. and just. that's an interesting but woefully underexplored dynamic. she also has the best approach (at first) in that episode which is to just like. talk to jenny like a peer. explain her worries over a shared pint of ice cream. it's only when she panics and starts Plotting that it becomes Too Much. anyway. there's a world in which their relationship was meatier and i want to live in it!
My unpopular opinion about this character: she deserved way better than the narrative throwing her under the bus to prioritize ch*ck.
One thing I wish would happen / had happened with this character in canon: i think i wish dan would have found out somehow about jenny getting drugged by agnes. on the one hand, nate telling him maybe would Kind of Not Be Cool, buuut it's tv the characters are allowed to be flawed and messy. plus! it makes the most sense. i feel genuinely feel that if dan found that out, she would be able to open up to him and they would figure out what was best for her (going to stay with their mom for senior year, lots and lots of therapy) sooner and without the ch*ck of it all.