#lesbian serena van der woodsen
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Modern Gossip Girl AU headcanons (Blairena edition w boys and other characters mentions at the end):
Tw: alcohol, addiction, noncon, ed and drugs mention but its all mostly already canon. (hey, it's Gossip Girl).
Trans headcanons and gay headcanons. Long post.
Social media:
Blair is a girlblogger, she has a tumblr and a meme instagram account where she blogs about all her thoughts on creative mode
She loves to dress in that aesthetic and in her public ig she posts some looks but they don't get the attention she'd like. She also makes a lot of custom designs and gives a modern twist to the old money, school girl looks she had on the original gg. She is very inspired by alternativ, artsy, recycled fashion styles.
This one time GG finds her blog/ig and exposes her and she gets very selfcounsious about it but at the end everyone likes what she posts so she gets way more followers and becomes very relatable. People find that she's very smart and deep and funny.
Blair likes reading and doing reviews of the things she reads, mostly novels.
When she starts her online journey she did it when she was in a bad place and felt very alone but when people show her love and support she gets comfortable with herself and her following.
Serena is known for doing tiktoks showing her outfits and she introduces Blair to tiktok and forces her to do challenges where they change outfits and ppl have to guess which style is who, that's how Serena introduces her bestie actually and her followers start shipping them.
Serena is a party girl, it girl influencer but her sunny personality makes her very likeable online and so she has a big following. She wears an outfit that B personalized for her once and everyone goes crazy for Bs designs so they start making content w Bs clothes.
Blair and Serena together are the moment, whether they are on a tiktok or walking to school together or at an event people are there for them bc their styles are so iconic and together they match in the best ways. They both basically look like rich monster high dolls. They get vogue to do a note on them and so on.
Sexuallity and gender:
B for Bi, Blair is bi, she is so certain about it since she kissed Serena when they were tweens bc Blair wanted to practice kissing but she was scared to tell Serena because for Blair feelings are very important and she didn't wanna ruin her friendship w S. (She totally posted a lot of situationships memes and blogged about it as a coping mechanism later).
Serena is pan at first but after dating a lot of guys and not falling really in love with any of them she realizes she's a lesbian cause being w Blair fills her with a much stronger kind of love that surpassed all of the others and suddenly her lack of romantic interest and why she can't commit in relationships makes total sense for her and everyone.
Blair is trans, she knew it since she was very young so she had an early transition. Her parents supported her a lot, Her mom being a designer and her dad being gay, they knew all about it. Serena ofc was w her for all of it and was the first to know. When they were little they liked to play dress up w their moms designer clothes and thats how everyone found out.
Serena goes by she/they pronouns, and there's a point in her life where she just doesn't give a fuck about gender or pronouns cause she's very free about it like why do we have to have gender... can't we all just be people? She's very that mentality.
They are very disrupting and that's what makes them so special, more of a force together.
Drugs, addictions and mental health:
Blair vapes and smokes weed, she started smoking with Nate and they just hang out to smoke and talk about feelings, at first Blair had a crush on nate cause he was so charming and they dated but... well you all know what happened. After that they were distant but grew together again as besties.
Blair had an ed and she had an ed twt, Serena made her delete it when she caught her crying with it open. After that she went to a clinic like in canon.
Serena struggles with an addiction with alcohol, she started to drink to cope with stuff, but then she abused it and got to a very bad place and after intervention from her friends she got sober but struggles w it sometimes, she relays on Blair for support.
(Tw noncon) Serena tried coke with Georgina but left it after Blair found out and got really upset about it. Blair got into a fight w georgina about this and the other noncon stuff she did to Serena in canon. Georgina gets cancelled.
Serena and Nate both have adhd and struggle together in class and then in life. Blair, Chuck and Dan helped them study.
Relationships (Everyone):
Like I hinted, Serena and Blair eventually get together. They are the main focus of the story, not in a romantic way but in a soul mates, best friends who love eachother kind of way, the romance ends up being all the things they do for eachother, the risks taking and the heartbreaks and finally the realization. Blair loves reading romance novels and wishes she were in one but little does she knows... until she realizes and starts to obsess with Serena as her prince charming.
Blair has a thing for Jenny at one point but then she sees Serena is dating Georgina and totally goes insane with jealousy and the need to get them apart. Jenny notices a fixation with Serena on Blairs side and gets emo and dark about it, teaming up with Georgina to get Blair and Serena apart. This doesn't work and Jenny realizes too late that she fucked up but at the end of it the only thing that was right was her intuition that there was something going on with S and B that was more than friendship. Jenny gets very heartbroken. She had pictured a life alongside Blair as very famous fashion designers, she hates Serena for taking that away from her.
Serena tries dating Dan and Nate. First Nate and she friend zones him, then Dan and they both realize they are gay together and become besties. Dan goes to Serena with relationship problems. Serena goes to Dan with Blair problems.
Nate, Chuck and Dan are together... Chuck and Nate were besties as kids but Chuck is basically Max from the new gg and started to have a lot of relationships while Nate is more of the romantic type. He falls for Serena first but in doing so he meets Dan and totally falls harder and fast for him. When they start dating Chuck notices and gets jealous, like someone touched his property. Chuck shares this with Blair and Blair just tells him to get over it and since he's the great Chuck Bass, he shouldn't have a problem with getting Nate back. Chuck tries this but Dan doesn't let him, they start an enemies to lovers arc fighting for Nate and then falling for each other. Is so much drama w them.
Georgina is obsessed with Serena in a toxic way, she can't stand Serena's love for Blair being stronger than Serenas love for Georgina so she does pretty nasty stuff to get Serena away from Blair, this ends up blowing up in her face and getting them closer than ever.
Chuck is also trans, his dad was not cool about it and he had a harder time transitioning but he did it anyways. Hes also bi like Blair. Him and Blair are the t4t it couple. They try dating like Serena and Dan but end up as besties who scheme together for Nate and Serenas (and then Dans) love. Nate is pansexual and Dan is gay. Nate uses he/they pronouns and feels about gender very much like Serena. Dan is the only one who is cis.
Well I know this is long but the thing is that I've been thinking about this since I watched gg for the first time like a year ago or smth. I know the fandom is very cishet but idk maybe someone likes this so I'm putting it out here.
#gossip girl headcanons#gossip girl fanfiction#blairena#waldsen#derena friendship#chair friendship#nerena friendship#gg headcanons#modern au#gg sm au#gossip girl social media au#gossip girl modern au#blair waldorf headcanon#serena van der woodsen#serena van der woodsen headcanons#blair waldorf#lesbian serena van der woodsen#bisexual blair waldorf#gossip girl#mine#trans gossip girl headcanons#gg is the friends we made along the way#gay dan humphrey#gay chuck bass#pan nate archibald#blerena#blair x serena#nate x chuck x dan
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Tag Game: Pick your top two favorite characters from five of your fandoms and explain why. Bonus points if the two characters have some sort of relationship (romantic, platonic, etc).
I was tagged by @talesofruby01. Thanks for the tag!
I did six fandoms, because at first I could only think of three and then I thought of six. Oh well.
Gilmore Girls - Jess Mariano and Paris Geller
Gossip Girl - Serena van der Woodsen and Jenny Humphrey (sorry Blair!)
Yellowjackets - Jackie Taylor and Shauna Sadecki née Shipman
The Marvelous Mrs. Maisel (TMMM) - Luke Kirby's Lenny Bruce and Astrid Weissman (sorry Imogene!)
The Vampire Diaries - Elena Gilbert and Katerina/Katherine Petrova/Peirce (Nina Dobrev supremacy!)
The Hunger Games (THG) - Katniss Everdeen and Peeta Mellark
Tagging: @dayenurose, @stellaluna33, @strideofpride, @hydesjackiespuddinpop
Explanations on my choices under the cut! You're about to find out way too much about me via the blorbos :)
Gilmore Girls - Jess Mariano and Paris Geller
Criminally robbed of the besties bonus points I deserve...
Jess Mariano is my character of all time. I'll fight you. The highlights: Jess comes from an abusive, loveless family situation and is a bit prickly from the ordeal (both to himself and others), but is just such a goodhearted and hardworking person that he gets out the other side with both loving relationships (with himself and others) and a good, safe life that he’s built for himself. Character of all time!!! Who does it for us like Jess Mariano?
Paris is incredibly ambitious and a little bit of a bitch (in a cool, sexy way), and therefore I love her. Also, your honor she’s a repressed lesbian. These things happen. And I will never get over how quickly she comes to understand Marxist theory when working her first job. She was never a snob; she literally was just never exposed to anything outside the upper-class.
My man Jess would have helped her with that and it would have been amazing. And he would have been comfortable living in that scary apartment with her (and Doyle) and Rory.
Gossip Girl - Serena van der Woodsen and Jenny Humphrey
When I have to shorthand my self, I say "I'm a Serena van der Woodsen type". The only reason I relate more to her than Jess in terms of self is because Serena and I shared the incredible lows of teenage girldom (plus we’re both exceptionally beautiful). Also, Jess never did drugs (cigarettes count, but they don't, also I don't think they were really a habit). Good for him! Don't do drugs! Serena definitely did drugs, and she started them (and boys, who don’t love her but sure do think she’s pretty!) very young. The incredible lows of teenage girldom... and how they stick to you into womanhood... She tries so hard to “change” when really she needs to change her situation, but that’s the struggle... How do you leave everyone and everything you’ve ever loved? And even if you could, is there really anywhere on earth you can escape the incredible lows of girldom/womanhood?
Which brings me to Jenny Humphrey. I’m not even gonna start on the incredible lows of teenage girldom because just watch the show, my poor girl... ANYWAY! Did I mention that I love seeing ambition in girls and women? She’s the living embodiment of going after what you want, *and she’s earned it*. She becomes Queen, not once, not twice, but THREE TIMES, and it was only sort of on purpose once!! And do not get me started on her high school fashion career. It kills me that her family wasn’t more supportive, but I know she’ll be successful because literally no one and nothing could ever stop her. And, I know this one is probably a hot take, but I honestly think she’s a really good person. She fights against the corrupting force of the UES better than most, and she is a really sweet and earnest person when she feels safe enough to just be herself.
Yellowjackets - Jackie Taylor and Shauna Sadecki née Shipman
Bonus points: They're in love! (Yes, present tense.)
Talking about teenage girldom and how it sticks to you into womanhood... I could write essays, but I'll just say this. Jackie is my favorite. She's most of us (I say assuming my experiences are universal). She is the metaphor for what happens when you devote yourself to the role assigned at teenage girlhood (it makes you repressed, i.e. the death of the self).
Shauna is a metaphor for all the fight it takes to survive teenage girldom into womanhood, and how it's a never-ending fight (she's the friend/lover, she's the mother/daughter, she's the hater/butcher/killer).
Teenage girldom is traumatic experience and it colors your adulthood, and that's the show, but also these two characters are the clearest metaphors on that main theme. Everything is a metaphor!!! Also, they're both sides of the repressed sapphic romantic-friendship. Hard relate, my girls!
TMMM - Luke Kirby's Lenny Bruce and Astrid Weissman
Some of you may be asking, Why not Midge? Why not Susie? Well, this is my list and I do what I want.
Luke Kirby's Lenny Bruce needs no explanation. He is the dream man. He's earnest and exceptionally romantic, and there's something about him you can't help find admirable to the point of inspirational. Maybe it's that he's brave and honest. Maybe it's that he's ambitious in that way that's hard to be as a woman. Maybe he's just really charming, because he's that for sure. But, of course, he's a mess too. Who isn't?
Astrid Weissman! She's so so so funny. She's not trying to be funny. She's not making jokes. She's just delightful! Also, all of us out there swimming in cultures that are not those in-which we were raised. Astrid Weissman has got you with her over-correcting, overcompensating, and just sheer enthusiasm. You go, Astrid!
The Vampire Diaries - Elena Gilbert and Katerina/Katherine Petrova/Peirce
Bonus points: They're related/doppelgangers!
UGH! If they aren’t the dichotomy of self, idk what is!!!
Elena is *such* a good person. She is literally the martyr she is such a good person. She loves and she will die for that love. That’s Elena. But it’s all about circumstances. Elena is an orphan (she had a beautiful, loving family before they died) suffering from survivor’s guilt, and she’s mostly keeping herself together with her love for her loved ones. If she isn’t living for them, she’s just gonna disappear.
Now, Katerina/Katherine, she’s got kind of the opposite thing going on. She had her newborn baby she loved very much ripped from her arms before being disowned by her family and banished from her hometown. She has no one who loves her and no one to love. She holds herself together with love of self or she’s just gonna disappear. And that she does. She is a ruthless pragmatist, because she has to be to survive. Because the world is harsh and cruel (and frankly really sexist), but she’s clever and strong, and she survives. That’s what she does. Elena dies for you. Katerina/Katherine survives despite you. Everything is a metaphor!!! My favorite thing about Katerina/Katherine is that she doesn’t *just* survive. No, she *loves* life. She’ll literally be being held captive by a vampire who has been hunting her relentlessly for hundreds of years, and she’ll take a moment alone in the house to drink and dance, because what’s a spare moment if it’s not being lived? Life is not just about survival.
THG - Katniss Everdeen and Peeta Mellark
Bonus points: They're basically soulmates!
Here's the thing. Katniss is a survivor/pragmatist with zero social skills, but an endless and earnest pit of love and enough passion to literally fuel a revolution.
Peeta is a child abuse victim who has learned to wield social manipulation (the charm offensive! plus literally lying!), but hasn't met an honest expression of emotion in his life (until he figures he's about to die so he might as well tell Katniss she's pretty) and doesn't know how to receive love.
They literally just fit each other. Peeta is charming when Katniss literally cannot. Katniss helps him survive when he's literally dying in a river camouflaged in mud and plants. But most importantly, Peeta teaches Katniss how to live in more than just survival mode, and Katniss reaches into her deep well of love and teaches Peeta how to be loved. Everything is a metaphor, but your honor, they are the couple of all time!!!
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I found one of my old AUs from my Gossip Girl Fanpage (I found quite a lot of edits to be fair), and idk, I felt like sharing 🤪
#one had to be sad#of course it was Chucks#btw Serena Van Der Woodsen is a lesbian#pass it on#gossip girl
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still not over this character
#a simple favor#blake lively#emily nelson#stephanie smothers#anna kendrick#kiss#lesbian#Bisexual#ryan reynolds#outfits#deadpool#gossip girl#stephanie x emily#anna kendrick x blake lively#serena van der woodsen
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Chapters: 1/1 Fandom: Gossip Girl (TV 2007) Rating: Teen And Up Audiences Warnings: No Archive Warnings Apply Relationships: Dan Humphrey/Blair Waldorf Characters: Blair Waldorf, Dan Humphrey, Dorota Kishlovsky, Nate Archibald, Serena van der Woodsen, Rufus Humphrey, Lily van der Woodsen, Jenny Humphrey, Eric van der Woodsen, mentions of Chuck Bass, mentions of Louis Grimaldi, mentions of a few other characters too but those are the two that probably need the most warning Additional Tags: AU after 4x20, Alternate Universe - Canon Divergence, Alternate Universe - Time Travel, Time Travel Fix-It, Not Chuck Friendly, mentions of abuse but nothing that wasn’t in the show, lesbian!Jenny, van der humphrey family meals my beloved, this is so domestic it’s not even funny Summary:
So, she’s woken up five years in the future. And she’s married to Dan Humphrey. And apparently works for Vogue too. Blair really, really hopes that she doesn’t have any children, this whole situation is strange enough as it is without Blair having to parent a child she doesn’t even know.
Or, Blair wakes up in a future in which she’s married to Dan.
#it's finally here!#only been talking about it for months lol#i may actually pin this one we'll see#dair#gossip girl#dan x blair#dan humphrey#blair waldorf#my fics#otp: dan loves me for me
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reasons vanessa abrams is the coolest gossip girl character
when she’s back in town after a year her first suggestion to dan is egging rich kids’ houses and slashing their tires for fun. nobody was doing it like vanessa abrams
she doesn’t take anyone’s bullshit, and isn’t intimidated by anyone, not even blair & chuck
it’s heavily implied that vanessa was super immersed in lesbian culture as an ally to her sister, and it’s also heavily implied that vanessa took nate along with her to lesbian events, which is objectively the best thing ever
had a threesome with hilary duff. need i say any more?
cares more about jenny’s problems in school than dan, her actual brother
spent blair waldorf’s seventeenth birthday flirting with serena van der woodsen
can objectively critique literature, even if she’s dating the person who wrote it (yes, this is a call out for dan)
driven, ambitious, etc but also creative!!
i definitely had more but i don’t remember. i started listening to hilary duff and now i can’t stop
#i always loved vanessa but realising how overhated she is makes me love her more tbh#vanessa abrams#gossip girl#found this in my drafts . going to bed#if anyone wants to add nice things about vanessa feel free
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Drop the Evie essay you wrote
okay so first of all it wasn’t really an essay the way some of my ramblings are, more like just me writing down all of my thoughts in a vaguely coherent manner bc my brain was running too fast to really organize it
and second of all, just to be on the safe side, these are the potential trigger warnings that I would give for the essay — I don’t know if they all actually come up or not, but better safe than sorry, so proceed with caution!
Potential TWs: being outed, parental neglect, character death (canon), suicide attempts (semi-canon), eating disorders, lots of mental health issues, and lots of general trauma and feelings of never being good enough, and canon typical references to drinking/drugs/partying/etc
so just like a fun fact, Evie’s vitamin water of choice is zero sugar strawberry lemonade and yes i spent too long reading reviews on different flavours all because gossip girl did an entire product placement episode
anyways now onto real thoughts let’s go lesbians let’s go
so okay evie has a... very negative experience with Lily’s various boyfriends and husbands. When Evie was younger she was always hopeful that this time would be different, that they’d be a family, that her mom would actually stick around, and every single time she’s been let down and left heartbroken. When her mom starts dating Bart, Evie is very against it but she just can’t be bothered to even try to talk to Lily — Lily will date him, maybe get married, play house, abandon her children, then get divorced, and the cycle will repeat, and Lily will never give a shit about how her children feel about it. Bart is just the latest rich man for Lily to set her sights on. Given the overall shittiness of most of Lily’s exes, Evie had figured she would be a lot more vocally against Lily dating again, but Bart...
Bart himself may terrify Evie, but Evie’s unwavering faith that Chuck will always protect her outweighs that fear, and Evie has long since given up on her mom caring about her opinions so she just takes comfort in the fact that Chuck will be there and tries to just ignore the rest — and the fact that Bart is pretty much always away does help with that. That being said, she was very distraught when Bart spends season 1 christmas with them, but then Bart’s “present” for her was flying Chuck home for a few days because Lily mentioned that Eric was teasing Evie about being excited about having Chuck as a brother, and he's trying to semi-win over the kids (aka bribe them into accepting him as Lily’s fiancé)
Evie speaks several languages! She started learning French and Spanish at a very young age, and then picked more up from Lily’s various husbands. She’s not fluent in all of them but she can hold conversations in eight languages — and four of them were from Lily’s boyfriends (and italian was half pieced together from French and Spanish), and she just keeps learning more because she tries to keep herself too busy to think at any given moment
Rufus is her favourite step-dad by far, but Chuck is her favourite step-sibling (and second favourite sibling, after Eric). That being said, Bart was surprisingly decent to her because even he quickly figured out that Evie has the innate ability to get Chuck to do basically anything, and he wanted her on his side, only he underestimated how much Evie hates him for treating Chuck like shit — as she says in 2x07, “if you want us to be a family, you should learn how to be a dad”
Evie has a bit of a thing for stealing coats lmao — it’s not unusual to find her stealing Chuck, Eric, Theo, or even Nate’s jackets when she gets cold or starts feeling particularly self conscious. At the housewarming party she actually gets to bothered by all the media watching her constantly that Chuck goes and gets her one of his blazers to replace the cropped one she was wearing, and she immediately feels a bit more at east
Evie is a jock like it’s understated but she’s on multiple sports teams at school and plays outside of school too — she’s also in dance classes several times a week, along with private vocal lessons, and being part of every theatre production at Constance Billard (musicals and plays), and is on the yearbook committee. Basically, Evie needs a fucking nap, and with a lot of pushing from Chuck and Eric and Theo (to balance out Blair “do absolutely everything in the name of Yale” Waldorf) she does eventually ease up on her extra-curriculars
She holds far too much power in the Constance-St Jude hierarchy. She’s a freshman, but it’s well known that Evie is completely untouchable. Some people (cough Jenny) might try to cross Blair, but no one is stupid enough to go after Evie — she’s not just Blair’s protégée, she’s also under Chuck’s protection. And when Jenny does try to cross her in season 3 (physical and emotional bullshit, public humiliation, telling the entire school she’d tried to kill herself and had been at Ostroff not “in florida”), well... she learns that even being family won’t stop her entire life from being destroyed
Speaking of Jenny... that’s a very messy relationship — I want to like Jenny, I really do, but I just... don’t so far. They’re a very sweet relationship early on, neither of them had dated before and they were just really smitten with each other and things were good. There were definitely some issues because of the Jenny-Blair war, but they’d been okay — or so Evie had thought, until Jenny dumped her by means of introducing everyone to her new boyfriend, Asher. Then of course there’s the party and Jenny outing her, and then just not talking to her for months until she needs something from them (an in to the White Party). Eric manages to convince Evie to play nice, but he does so under the impression that Jenny had apologized to Evie — he didn’t know she’d only apologized to him. Eventually Jenny does apologize and Evie tries to forgive her, and she keeps giving Jenny more and more second chances (especially once they become step sisters), but Jenny really just keeps hurting Evie to get on top because with Blair gone, Evie immediately becomes the new queen, and Jenny cares more about being queen than being nice. Little does she realize that part of why Evie became queen with no challenge is because she’s nice.
and regarding Evie’s other relationships... so serena was a really good big sister when Eric & Evie were kids — Blair was the responsible sister and Serena was the fun sister, but it was a good balance and it worked. But when the twins were around eleven and Serena was around 13, she became besties with Georgina Sparks, and everything went to shit. Serena started getting into partying and drinking and drugs and became just as flighty and unreliable as Lily, which takes a significant toll on the twins’ mental health — side note, one of their therapists at the Ostroff Centre believes that their significant codependency stems from the abandonment issues they have as a result of Lily and Serena just up and leaving them whenever anything “better” comes along.
And unfortunately for the twins, this was around the same time (grade 6) that Theo got sent to boarding school, so really they lost both their sister and their best friend at the same time, and Theo leaving also messed up the overall group dynamics and they half lost Nate too — he was still in their lives but he went from being the dad to Blair’s mom to being more of a big brother, and there was this sort of hole that didn’t get filled until a couple of years later.
And of course, a lot of it then fell to Blair to try to fill that hole and the holes left by Serena and Lily and went from being sort of “mom friend big sister” to “literally the closest thing we have to a mom”, which is also just a lot of pressure for a thirteen year old girl and part of why Blair and Chuck got a lot closer after he ended up becoming their dad was because she finally had someone that she could talk to too.
Also like full disclosure, Chuck never really intended to become their dad. He started off as a reluctant big brother because he was Nate’s best friend and Nate was the dad friend when they were younger, and Evie just kind of decided that she loved him and like no one can argue with Evie so all of a sudden he was part of the family. He doesn’t really become dad until the van der Woodsens move into the hotel because suddenly Eric and Evie are just always there, and he doesn’t even realize it until months later, after Serena is gone and he realizes that he’s been skipping parties to like play mario kart and shit with the twins and Blair is just like “lmao yeah buddy you’re the last one to get this memo”
and then there’s this list that I made of the NJBC’s roles in raising the twins and theo back when they were younger
Blair: holds their hands to cross the street, teaches them not to talk to people who wear sneakers or to strangers, teaches them how to dress themselves like respectable people, makes them finish their homework before watching tv, hates all of their nannies and only trusts dorota to take care of them Nate: teaches them to tie their laces and their ties, plays video games and sports with them, helps them with homework and doesn't get impatient when they struggle, lets them use his notebooks to draw in when they're bored Chuck: will destroy anyone who hurts them, teaches them street smarts and how to tell when someone is lying, is the one who lets them do dumb and reckless things because he'd rather they do them when he's there to get in trouble, still refuses to believe that they know what sex is Serena: reminded them that it's okay to have fun and draw outside the lines, stood up for them when lily was being a shit mom and always tried to protect them from the worst of her neglect, came up with games to play when they were sad to take their minds off whatever is upsetting them
And Theo!!!!!! Theo has been their best friend for their entire lives! They’ve known him since they were babies and the three of them have always been inseparable! Like highkey they were just a more functional NJBC lmao, and we love them for it! Theo getting sent to boarding school was really hard on all three of them but they stayed in constant contact and whenever Theo is back in the city, it’s almost impossible to see them not together. Theo does know that they were in the Centre, so once he’s back full time, he’s spending as much time visiting them as he can! Even when Eric and Theo are dating (and later when Evie and Theo are dating), the group dynamics really never change! It’s still always the three of them, and sometimes Jenny in s1, they’re still each other’s family, and they’re still just a bit too interdependent to be entirely healthy (it’s the trauma and neglectful parents)
on a slightly related note, neither of the twins drink anything other than champagne and sometimes wine, and neither of them touch drugs at all, and it’s entirely because of Serena. They’ve both seen how much she’s changed since she got into that scene, and especially since ‘liking partying’ turned into ‘alcohol addiction’, and they’re both too afraid of ending up like that to even take the risk. It’s something that definitely sets them apart from pretty much any of their peers, but they’ve gotten very good at just laughing it off with a “hey, I just don’t want to end up on Gossip Girl tomorrow” which people generally accept
(that being said, Evie did smoke for a while pre-canon bc cigarettes curb hunger, but she hasn’t smoked at all since ending up in the Centre, and once she’s out too many people have an eye on her for her to even try, and she does want to stop)
(TW ATTEMPTED SUICIDE, fairly detailed discussion) so okay the breaking point for the twins... lily had just gone awol again and Blair was away visiting her dad and evie was at the archibalds’ house hanging out with theo, who was home for a weekend, and eric didn’t want to call anyone because lily’s disappearance had left him in a spiral of feeling annoying and like people didn’t really want him in their lives and there wasn’t a specific trigger but instead of the spiral slowing down or evie/chuck/blair being able to pull him out of it, it just kept getting worse until he was slitting his wrist in the bathroom — only Evie had just gotten home and when he didn’t reply to her calling his name, she got freaked out and started looking for him and when she saw him, she just... couldn’t deal. She called 911 for eric but then she was just in the bathroom and covered in his blood and she didn’t know what to do and she needed to calm down so she grabbed a bottle of valium that she thinks was Lily’s but instead of just taking one pill she ended up taking all of them and downing them with a bottle of vodka serena had hidden — once she realized what she’d done she called Chuck and basically just said “I think I fucked up” and Chuck freaks out (understandably) and rushes to their suite and gets there basically just in time to see both of them being loaded into an ambulance; he claims he’s their brother and rides with them to the hospital where he calls blair, and arranges for his jet to pick her up asap, and then tries (unsuccessfully) to get in touch with lily
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thanks to jj’s post here and because it’s pride month, here’s a list of my muses’ sexualities. of course this doesn’t mean i am only interested in romantic ships but it’s an easier way to make my mutuals feel safe and comfortable when approaching me.
agatha night (caos) — aromantic/bisexual.
zelda spellman (caos) — bisexual.
donna troy (dc comics/titans) — bisexual.
lena luthor (supergirl) — bisexual with preference for women.
lucy lane (dc comics) — bisexual.
sara lance (dctv) — bisexual.
wally west (dctv) — bisexual.
lorelai gilmore (gilmore girls) — bisexual with preference for men.
serena van der woodsen (gossip girl) — bisexual.
callie torres (grey’s anatomy) — bisexual.
ella montgomery sloan (grey’s anatomy oc) — lesbian.
mark sloan (grey’s anatomy) — heterosexual.
aaliyah zabini (harry potter) — heterosexual.
angelina johnson (harry potter) — bisexual.
bellatrix black (harry potter) — aromantic/heterosexual.
emmeline vance (harry potter) — lesbian.
gideon prewett (harry potter) — heterosexual.
gwenog jones (harry potter) — lesbian.
padma patil (harry potter) — lesbian.
pansy parkinson (harry potter) — bisexual.
tracey davis (harrypotter) — lesbian.
zoe hart (hart of dixie) — bisexual.
morgana pendragon (bbc’s merlin) — bisexual with preference for women.
andrea labonair (the originals au) — bisexual.
lizzie saltzman (legacies) — bisexual.
rebekah mikaelson (tvd/the originals) — bisexual.
emma swan (ouat) — bisexual.
regina mills (ouat) — bisexual.
abigail thompson (dhampir oc) — bisexual.
courtney difronzo (mafia oc) — bisexual.
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her character is basically serena van der woodsen turned lesbian.
OKAY BUT WHY IS NOBODY TALKING ABOUT BLAKE LIVELY’S WARDROBE IN THIS NEW SIMPLE FAVOR MOVIE LIKE
LORD PLEASE
#what a wonderful combination#the style omg jevgzjdvvzgf#blake lively#serena van der woodsen#gossip girl#a simple favor#outfit#lesbian
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Gay- Serena Van Der Woodsen
Pairing: Serena Van Der Woodsen x Reader
Characters: Serena Van Der Woodsen
Warnings: N/A
Request: Anon- A Serena Van Der Woodsen imagine where the reader comes out (as gay) to Serena and Serena confesses her feelings? Thank you or running this blog, it’s great.
Word Count: 457
Author: Charlotte
When you arranged for your close friend to come over for a drink, it seemed like a good idea but seen as you knew that you wanted to tell her something terribly important, you were very fearful of what would come from it. Serena had been your friend since you wore nappies, your mothers having been friends since school as well. Although you had been dear friends for as long as you could remember, you pretty much always knew that wasn’t the full extent of your feelings.
It was a hard fact that you fought with throughout your teen years and now into your early adulthood. All you had ever been taught as acceptable was being heterosexual but deep down you knew that you had far more interest in women. You tried to fight it and even dated and slept with men, but you never felt anything for them.
Finally, you had come to fully accept yourself and you hoped that your best friend would feel the same. You doubted that she would ever love you in return but all you could hope was that she would still want to be your friend after she found out that you were a lesbian.
When she arrived, the two of you talked for a bit before she noticed your nerves. It wasn’t normal for you to be so nervous and she knew that.
“What’s wrong?” She asked.
You took a deep breath, knowing it was now or never.
“I need to tell you something Serena,” you sighed. “And I just really hope that you don’t hate me for it.”
“I could never hate you,” she assured, reaching across the table to take your hand.
“I’m gay.”
Maybe you could have thought of a more eloquent way to tell her about your sexuality but at least it was out there now. Now she knew you liked women and it was just down to her reaction.
“How long have you known?” She asked softly.
You shrugged your shoulders. “I guess I’ve always known. Once I first found a girl that I liked, I realised I never actually liked the any of the guys whom I had seen.”
She cocked an eyebrow at you.
“Who was your first female crush?” She questioned.
You paused. You hoped you wouldn’t have to tell her that part.
“Um… it was actually you.”
Serena let out a laugh. “And how do you feel about me now?”
Your cheeks became bright red as you saw any form of escape disappear from your sights.
“I feel the same.”
A smile curled onto her lips. She didn’t say anything more, rather leaned across the table until her lips pressed against yours. That went a lot better than you imagined.
#Gay#Request#Anon#Serena Van Der Woodsen#Serena Van Der Woodsen Imagine#Serena Van Der Woodsen One Shot#Gossip Girl#Gossip Girl Imagine#Gossip Girl One Shot#GG Imagine#GG One Shot#GG#Charlotte
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Serena van der Woodsen is a lesbian
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Love, Simone (Chapter 5)
Chapter 1, Chapter 2, Chapter 3, Chapter 4
Sorry for not posting an update in so long guys! Finally got around to Chapter 5, hope you all like it!
Words: 1442 It had been several weeks since Simone had caught you with your pants down in the shack at school. She had tried to process her feelings, but all of them had led to an answer that she was too afraid to confront. Was she really jealous of the fact that you had been making out with someone who wasn't her? Or was it just fear that she was not the only girl in your heart anymore? Emily had never thought about being with women, but now that she has taken time to think about it, there was no one she’d rather be with than you.
All of these questions seemed to lead to one conclusion: Emily wanted to be with you, as more than a friend. However, that also begged the question of how long she had been feeling this way. Emily liked men, that much was for certain. But now, there seemed to be a possibility that she liked women too, a possibility that she had never considered before. Sure, she had looked at attractive girls a certain way, but she never considered being with them an option. It seemed like her feelings wanted to be known, but she was just too scared to admit it. There was no doubt that she had always liked you, she’s just never considered being with you an option until now.
With these thoughts swirling around her mind, she thought it would be best to search online for people who may have felt exactly what she was feeling now. She knew she was most likely not the first person (or the last) to feel this way about her best friend.
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It wasn’t like you had been cheating on her or anything, so there was no reason for her to be mad or upset about what you had done. The thing was...she was acting distant like somehow your friendship had changed just because you decided to move on and be with someone else.
There were only a few people who were “out” at school, and Emily thought that it would be best to enlist the help of people who may have gone through what she is experiencing at the moment. She was finally directed to the teacher who most of the students knew to be gay. It felt scary going up to a teacher to ask questions about their sexuality, but Emily believed that if anyone knew what she was going through, it would be Ms. van der Woodsen.
“Hi Ms. Woodsen, can I ask you a question?”
“Yes, Emily is it? How can I help you? Besides, you can call me Serena when we’re not in class.”
“I think I have a problem. My best friend, who has recently come out to me as a lesbian, has found someone who she seems to like. I don’t have a problem with that, but it seems like I don’t like it at the same time. It feels like the person she found can’t treat her right, only I know everything my friend likes. But I’ve only ever dated guys, and I don’t think I’ve ever felt, you know, like that towards any of the girls I’ve been around.”
Serena smiled as she looked at Emily. “I believe the word you’re looking for is ‘jealousy’.”
“Pfft, why would I be jealous? I don’t even know for certain if I like girls, that way.”
“Well, in my opinion, the fact that you’re here to tell me about how you feel about your friend shows a lot. Maybe more than you know. I think it would be best to go home and think about why you went through all the trouble of figuring out why you feel the way you do. Maybe taking a few nights to think it over will clear things up.”
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As time went on, Emily realized that she couldn’t find a good reason as to why she went through all the trouble of finding out why you being in a relationship with Taylor was bothering her. All of her reasons came back to an image of you and her, together holding hands. Even the thought of the two of you together in her bedroom, laughing until your sides hurt, made Emily miss you. The fact was that Emily has had feelings for you ever since the two of you started spending time with each other. Sure, her feelings had been platonic (or so she thought), but ever since she realized you were a lesbian it was like there was something different between the two of you. Maybe there might be something more between the two of you if she wanted to take the leap.
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Emily absent-mindedly rode her bike up and down her block as she waited for you to come over. Her parents had left for the day, and she knew that the two of you could have the privacy to talk about what’s been on her mind. Finally, she saw your car pull up in her driveway and ran over to open the gate.
After you walked with her into her house, there came a period of awkward silence as the two of you sat, waiting for the other to speak first. Finally, it was Emily who broke the silence.
“It’s been a while since I’ve seen you. Several weeks in fact.” You saw Emily’s face lower in embarrassment. This caused you to hesitate from making any more scathing remarks about Emily’s recent behavior. Maybe she wanted to use this chance to explain why she had been acting so strange around you.
“Well. I guess I should explain myself a bit, huh?” Emily fiddled with the cup in front of her, and it seemed like she couldn’t (or wouldn’t) meet you in the eye. You waited for her to speak as the silence stretched on. Minutes seemed to drag on for hours as Emily opened and closed her mouth several times. “I don’t have any problem with you being gay.”
“Which hasn’t been demonstrated by the fact that you have been avoiding me for the past few weeks. Ever since you caught me making out with Taylor.”
“Why did you keep that relationship from me? I thought we were friends! We told each other everything.”
“We are friends! I didn’t think it mattered that much! It wasn’t like my ‘relationship’ with Taylor was serious or anything. It wasn’t important enough for me to say anything!”
“It’s just that --” Emily’s voice cracked. It hurt you to see her like this, tears in her eyes and not looking directly at you. “It just seems like things have changed ever since you came out. I know you’re still you, but it just seems like something between us has changed. What’s wrong, Simone?”
“Because you’re you, Emily. We’ve been friends since kindergarten, and I’ve realized I have been in love with you ever since the day we met. Ever since I realized I had feelings for you, I knew that I would do anything to be with you. Whether it means I get to be with you the way I want truly want to be or being your best friend and pretending I’m not in love with you, I knew I would do anything for you.”
Emily looked down awkwardly and fiddled with the cup in front of her. “You know, I’ve been thinking of me. Of my feelings, more specifically.”
“What about your feelings?”
“I’ve been thinking about why I’ve been acting weird for the past couple of weeks. I don’t know, it might be because I’m feeling jealous.”
“Jealous about what?” This situation was becoming more and more confusing by the second.
“Jealous over the fact that you liked someone, and that person wasn’t me. That has been why I’ve been avoiding you. I didn’t how to react to the way I was feeling.” Once Emily started talking, it was like she wanted to get everything out in one go before she could stop herself.
“So...what are you saying? That you have feelings for me too?”
Again, there was a long period of silence before Emily spoke. “I am saying that I believe I’ve always liked you. As a best friend, and possibly as something more.”
“Does that mean that you want to be with me?”
“Maybe we can figure this out? Over dinner? At your favorite place?” Emily looked scared, afraid that her actions had pushed you away for good.
“I would love to.” You were unsure of where this road might take you, but if there was anyone that you wanted to explore the unknown with, Emily was the one you would choose.
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My angel, sweet twin @daddybarnaclebarnum tagged me in this thing, and I have a few people in mind automatically BUT DO I HAVE FIVE?! We shall have to see. Also I have a chance to showcase my gayness.
LETS GO, LESBIANS.
#1 Shay Mitchell.
I’ve been in love with her since I first saw Pretty Little Liars. If you don’t think she’s perfect you can form an orderly queue and fight me.
#2 Hilary Duff
This love has lasted since Lizzie McGuire and now I’m even more in love. She’s my favourite Disney star, and I’ll always be a loyal fan. Also have you seen her face lately?
#3 Olympia Valence
I don’t think I need to explain this one. Just look at her. Wow, it’s hot in here.
#4 Blake Lively
Serena Van Der Woodsen. 💦
#5 Margot Robbie
Words aren’t necessary. Lesbihonest.
I don’t know that many blogs by memory so everybody do this. @mitsukoxaki @sundaydrivexo @lungstofill @macabremusings @thereismylittlerainbow
#babes#shay mitchell#hilary duff#olympia valance#blake lively#margot robbie#girls who like girls#lesbian#i am so gay i cant control it
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Maya’s brother threw a dinner party at his house and Kaitlyn showed up wearing a dress that’s more Gossip Girl than Willow Creek family dinner 😁
Although I did kind of base Kaitlyn off of Serena Van Der Woodsen (except less scandalous and lesbian instead of straight) who I had a crush on when I used to watch Gossip Girl 😊
#ts4#mysims#Maya Feldman#Kaitlyn Chen#Luna Feldman#Alicia Feldman#Maya's mom is a little scandalized#She's kind of old fashioned but nice
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17 + Serena and vanessa
“okay, but this is really important,” vanessa murmurs, whispering in serena’s ear. “i know this doesn’t mean anything to you, and frankly, it doesn’t mean anything to me, either, but there are people around us, and if we get in trouble, it could be really bad.”
“come on, isn’t that half the fun?” serena grins, flipping the page of her magazine, drawing a clownfish on a male model’s abs. “you dated nate, don’t tell me you didn’t show up to high society events, well... high.” she giggles.
“on the contrary, i kept him sober,” vanessa says, poking at serena’s shoulder. “well, i tried.”
“you would,” serena says, laughing softly, kissing vanessa’s cheek. vanessa can feel people’s eyes on them, and she swallows.
“i need you to behave,” she says, softly.
“we both know i’m not good at that,” serena says cheerfully, laughter in the tone of her voice. and then she catches the look on vanessa’s face. “what’s wrong?”
vanessa shakes her head. “it’s nothing.”
serena puts her magazine away, uncrosses her legs and sits properly, quickly rearranges her hair with her fingertips, and looks put together. “there, i’m behaving. now. tell me?”
vanessa exhales. “i don’t think your grandmother likes me.”
“cece?” serena asks. “don’t take it personally, she doesn’t like anyone.”
“no, i mean, i think she really hates me,” vanessa says, quietly.
serena puts an arm around her. “what did she say to you? did she blame you for my misbehaviour? she was really horrible to dan, once, and i know she can be bigoted and mean.”
vanessa sighs. “i never felt like this with nate,” she says, softly. “maybe because nobody was accusing me of turning him lesbian, i don’t know.”
serena snorts. it’s an unnatractive snort. “neither of us is even lesbian.”
“tell your grandmother that,” vanessa says, and then blinks, as if startled to have said it.
serena laughs, covering her mouth with her hands to stifle it. “yeah, i’m sure she’ll understand. maybe she’ll even drive the float when we go to pride together. i can see her behind the wheel...”
the image is too much for vanessa, who smiles despite herself.
“let’s get out of here,” serena says.
“it’s the van der woodsen family dinner, can you get out of here?”
“vanessa, you are my family,” serena says quietly. “more than them. so yes, i can get out of here. i’m doing it right now. let’s go. can you drive a car?”
“i’ve got the keys to the lincoln hawk van,” vanessa says.
“dan never had the keys to the lincoln hawk van,” serena says, awed.
“well, obviously not, i’m cooler,” vanessa says, smiling.
serena leans over, kisses her forehead, takes her hand and marches out of the room with her. “you absolutely are,” she says.
#long post#serenessa#gossip girl#my writing#i feel like i should slap this under a read more but i don't know where i'd put it#so im just tagging long post instead LKDHLKGH#sorry this got angsty!!#we did get happy ending city tho
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so we all know that serena van der woodsen is a lesbian and when she gets back from boarding school in s1 she’s like “blair i did sleep with nate but only because i was struggling with my sexuality and now i know i’m a lesbian!” and proceeds to date Brooklyn Butch Lesbian Dan Humphrey BUT! the other side to this story is part of her sexual awakening to begin with is carter baizen, former upper east side wild child, who had many ~sexual tension filled~ exploits with serena...even if serena was too unwilling at that point to admit what was going on, carter sure as hell knew serena was into her. anyway so carter ditches her family and the entire upper east side for a while (because of their homophobia i assume) but eventually, unwillingly, returns to the fold (because she needs money). but hello, at least serena van der woodsen is apparently openly into girls now! so thus begins carter and serena’s story throughout the seasons, which yes, one day will end up with them getting married and settling into a more exciting and appropriate-for-them version of domestic bliss
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