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* BrokenBase: Whether Blair should end up with Chuck or Dan. At-the-time showrunner Josh Safran was wholly on board the Dair train and believed that the divide was about 50/50. In truth it was closer to 80/20 in Chair's favour, and when Josh Schwartz and Stephanie Savage re-took the reins for the final season they steered the show back towards Chuck and Blair, hoping to salvage the ratings. It worked so-so.

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* BrokenBase: BrokenBase:
**
Whether Blair should end up with Chuck or Dan. At-the-time showrunner Josh Safran was wholly on board the Dair train and believed that the divide was about 50/50. In truth it was closer to 80/20 in Chair's favour, and when Josh Schwartz and Stephanie Savage re-took the reins for the final season they steered the show back towards Chuck and Blair, hoping to salvage the ratings. It worked so-so.so-so.
** Newer viewers finding the show on streaming services are far less tolerant of Chuck's repeated sexual assaults and exploitation of women on the show than most of the viewers were during the original TV run. This also has a side effect of these new viewers liking the canon Chuck & Blair relationship far less than others on the show such as Dan & Blair.
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** In the Season 2 finale, Blair makes a joke about Chuck being spotted in France, Germany and Italy on the Gossip Girl Website after which she says "I hope he has so much fun that they have to quarantine him." Considering the Coronavirus outbreak of 2020 which hit Italy, France and Germany the most, this joke takes a much darker turn.

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** In the Season 2 finale, Blair makes a joke about Chuck being spotted in France, Germany and Italy on the Gossip Girl Website after which she says "I hope he has so much fun that they have to quarantine him." Considering the Coronavirus outbreak of 2020 which hit Italy, France and Germany (and the most, rest of the world), this joke takes a much darker turn.

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* DarknessInducedAudienceApathy: Because the show revolves around a bunch of heavily flawed and polarizing characters who can be be very dishonest and unsympathetic towards each other in their own different ways, it can be a bit difficult to really root for any character when things go south for them or to even care at all if they forgive each other.


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* TooBleakStoppedCaring: Because the show revolves around a bunch of heavily flawed and polarizing characters who can be be very dishonest and unsympathetic towards each other in their own different ways, it can be a bit difficult to really root for any character when things go south for them or to even care at all if they forgive each other.
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Jail Bait is now a disambiguation. Deleting/replacing wicks as appropriate


* TestosteroneBrigade: To go along with the aforementioned EstrogenBrigade, the show also had a lot of male fans who watched it for Creator/BlakeLively, Creator/LeightonMeester, Creator/MichelleTrachtenberg, Creator/TaylorMomsen ([[JailBait for teenagers]]), Kelly Rutherford (for [[LikesOlderWomen fans of older women]] and/or ''Series/MelrosePlace'')... and that's just the regulars/semi-regulars.

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* TestosteroneBrigade: To go along with the aforementioned EstrogenBrigade, the show also had a lot of male fans who watched it for Creator/BlakeLively, Creator/LeightonMeester, Creator/MichelleTrachtenberg, Creator/TaylorMomsen ([[JailBait ( for teenagers]]), teenagers), Kelly Rutherford (for [[LikesOlderWomen fans of older women]] and/or ''Series/MelrosePlace'')... and that's just the regulars/semi-regulars.
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** Also Nate's relationship with Catherine after Chace Crawford began dating Erin Andrews who is 8 years his senior
** The second season focuses on Blair's feelings of jealousy towards Serena and the way she kind of coasts through life getting handed the things she wants. In real life Blake Lively and Leighton Meester don't get along, apparently not interacting unless they have to. The reason? It's said that Leighton dislikes how Blake has managed to become a sensation despite her character not being as popular (some would also say well rounded) as Leighton's because of her beauty and A-list boyfriends.

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** Also Nate's relationship with Catherine after Chace Crawford Creator/ChaceCrawford began dating Erin Andrews who is 8 years his senior
** The second season focuses on Blair's feelings of jealousy towards Serena and the way she kind of coasts through life getting handed the things she wants. In real life Blake Lively Creator/BlakeLively and Leighton Meester Creator/LeightonMeester don't get along, apparently not interacting unless they have to. The reason? It's said that Leighton dislikes how Blake has managed to become a sensation despite her character not being as popular (some would also say well rounded) as Leighton's because of her beauty and A-list boyfriends.
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** Agnes roofies Jenny and then abandons her at a club surrounded by men having a bachelor party, with the express purpose of [[RapeByProxy getting her raped.]] Agnes does this as revenge for Jenny [[DisproportionateRetribution contacting potential clients with her behind Agnes’ back]] back in Season Two— ''which she already burned Jenny’s dresses and kicked her out for.''

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** Agnes roofies Jenny and then abandons her at a club surrounded by men having a bachelor party, with the express purpose of [[RapeByProxy getting her raped.]] Agnes does this as revenge for Jenny [[DisproportionateRetribution contacting potential clients with without her behind Agnes’ back]] back in Season Two— ''which she already burned Jenny’s dresses and kicked her out for.''
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** Agnes roofies Jenny and then abandons her at a club surrounded by men having a bachelor party, with the express purpose of [[RapeByProxy getting her raped.]] Agnes does this as revenge for Jenny [[DisproportionateRetribution contacting potential clients with her behind Agnes’ back]] back in Season Two— ''which she already burned Jenny’s dresses and kicked her out for.''
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** In the early episodes of the first season many fans preferred the combo [[BirdsOfAFeather Chuck/Blair]]-[[YourCheatingHeart Nate/Serena]]-[[UnluckyChildhoodFriend Dan/Vanessa]] to the then [[OfficialCouple Official Couples]] [[StrangledByTheRedString Nate/Blair-Dan/Serena]], but never thought the writers would abandon Nair or Darena. Fast forward to season 3, and Chair-Serenate-Danessa are the current pairings.

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** In the early episodes of the first season many fans preferred the combo [[BirdsOfAFeather Chuck/Blair]]-[[YourCheatingHeart Nate/Serena]]-[[UnluckyChildhoodFriend Chuck/Blair]]-Nate/Serena-[[UnluckyChildhoodFriend Dan/Vanessa]] to the then [[OfficialCouple Official Couples]] [[StrangledByTheRedString Nate/Blair-Dan/Serena]], but never thought the writers would abandon Nair or Darena. Fast forward to season 3, and Chair-Serenate-Danessa are the current pairings.

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* FamilyUnfriendlyAesop: Close to the end of the series Dan becomes the world's biggest ass to his UES friends [[spoiler:(not to mention the reveal what's been all along)]] and [[JerkJustifications insists that it means being "one of them" and "finally gaining their respect"]]. His actions are not portrayed sympathetically. Dan's father, the local paragon of morality, is disgusted. Dan's friends are also disgusted. And then they forgive him, accept as one of them, rave [[spoiler:at the information he's been Gossip Girl all along]], he gets the girl, happy ending.



** As of Season 4, Vanessa has no friends left, among the characters or the viewers. Frustrated with how the NJBC seem to [[{{Karma Houdini}} always escape the consequences of their actions]], she gave up the integrity that used to separate her from them in an ill-advised and ill-fated attempt to beat them at their own game. [[{{An Aesop}} Now she's just the dog sitting next to a river, watching her steak float away]], and even her fans want her to Just. Go. Away.

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** As of Season 4, Vanessa has no friends left, among the characters or the viewers. Frustrated with how the NJBC seem to [[{{Karma Houdini}} always escape the consequences of their actions]], she gave up the integrity that used to separate her from them in an ill-advised and ill-fated attempt to beat them at their own game. [[{{An Aesop}} [[AnAesop Now she's just the dog sitting next to a river, watching her steak float away]], and even her fans want her to Just. Go. Away.
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* VindicatedByHistory: Back in the show's heyday, the pairing of Dan and Blair was only seen as an obstacle for Blair and Chuck's relationship, and was overall less popular than it was. Nowadays, while some fans still have this mindset, the ship has grown a lot in popularity and has many devoted fans. Claiming it one of the most mature, if not the most mature, relationships on the show.
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* Chuck, probably because hes the wish fufillment type that does shady things and gets away with it while having the main female fall for him to add towards the man fantasy sex machine wankage.

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* ** Chuck, probably because hes the wish fufillment type that does shady things and gets away with it while having the main female fall for him to add towards the man fantasy sex machine wankage.
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* Chuck, probably because hes the wish fufillment type that does shady things and gets away with it while having the main female fall for him to add towards the man fantasy sex machine wankage.
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** Serena gets so much hate from both old and new fans that she's bordering on this territory. This mainly stems from the fact that she [[KarmaHoudini doesn't suffer any major consequences for her malicious actions later in series]] unlike her friends and peers. Her decisions and thought process makes her come across as misguided at best and a DesignatedHero at worst. Doesn't help that she's also supposed to be the main character. Key words here being [[OutOfFocus "supposed to be".]]

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** Ed Westwick and Creator/LeightonMeester had quite the following, most of it on Website/LiveJournal. Jessica Szohr, who was dating Westwick at the time, got the DieForOurShip treatment. Of course, it doesn't help matters that there is a video up on Website/YouTube where [[https://www.youtube.com/watch?v=-PHo-yBBB70 Westwick curses like a sailor]] over Meester leaving a party with her boyfriend.
*** Also doesn't hurt that Meester is infamous for ad-libbing lines in their scenes together. Including "If I were you, I would have rode me harder."
*** And Westwick's comment in an interview: he hopes Chuck and Blair will get back together because "I like kissing Leighton".
** Matthew Settle and Kelly Rutherford, who play Rufus and Lily, have also gotten this treatment.
** On the flip side, then-actual couple Penn Badgley and Creator/BlakeLively got practically none of this.

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** Ed Westwick Creator/EdWestwick and Creator/LeightonMeester had quite the following, most of it on Website/LiveJournal. Jessica Szohr, Creator/JessicaSzohr, who was dating Westwick at the time, got the DieForOurShip treatment. Of course, it doesn't help matters that there is a video up on Website/YouTube where [[https://www.youtube.com/watch?v=-PHo-yBBB70 Westwick curses like a sailor]] over Meester leaving a party with her boyfriend.
***
boyfriend. Also doesn't hurt that Meester is infamous for ad-libbing lines in their scenes together. Including "If I were you, I would have rode me harder."
***
" And Westwick's comment in an interview: he hopes Chuck and Blair will get back together because "I like kissing Leighton".
** Matthew Settle Creator/MatthewSettle and Kelly Rutherford, Creator/KellyRutherford, who play Rufus and Lily, have also gotten this treatment.
** On the flip side, then-actual couple Penn Badgley Creator/PennBadgley and Creator/BlakeLively got practically none of this.
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** Likely also a result of retooling after the PilotEpisode. The original intention was likely to position Chuck as the antagonist rather than an anti-hero protagonist.
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** Many fans (especially Dair fans) like to pretend season 6 as a whole doesn't exist.
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** Other examples include Derena (Dan/Serena), Nair (Nate/Blair), Serenate (Serena/Nate), Nenny (Nate/Jenny) and Rufly (Rufus/Lily).

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** Other examples include Derena (Dan/Serena), Nair (Nate/Blair), Serenate (Serena/Nate), Nenny or Jenate (Nate/Jenny) and Rufly (Rufus/Lily).
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Deleting Natter/an attempt at a Justifying Edit.


*** Georgina made Serena's life hell in late Season 1 without any provocation that I can see. In fairness, though, she tried to make amends for that in late Season 2.
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** Gossip Girl title remixes are becoming popular on places like Twitter. That's editing the title to spell out answers for Blair to statements by Serena. One of the more common if not first one is [[SignificantAnagram "Go piss Girl"]].
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** [[spoiler: Dan Humphrey]] did everything ever. Won [[Series/{{Glee}} Nationals]]. Killed Disney/{{Bambi}}'s mother. [[Series/PrettyLittleLiars Is A]]. Is Series/VeronicaMars. [[Franchise/StarWars Luke's Father.]] [[Series/HowIMetYourMother Ted's Wife]].

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** [[spoiler: Dan Humphrey]] did everything ever. Won [[Series/{{Glee}} Nationals]]. Killed Disney/{{Bambi}}'s WesternAnimation/{{Bambi}}'s mother. [[Series/PrettyLittleLiars Is A]]. Is Series/VeronicaMars. [[Franchise/StarWars Luke's Father.]] [[Series/HowIMetYourMother Ted's Wife]].
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Sister Ship is being cut per TRS; already mentioned under Ship Mates


* SisterShip: Chuck/Blair and Nate/Serena are this to each other.
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** Jenny and Agnes, before things go sour. They become friends and then roommates ''very'' quickly, and have moments that come off as flirtatious, such as Agnes vampishly asks Jenny if she’s “[her] bitch,” which Jenny agrees to. They even end up taking their shirts off and dancing together, to Music/{{Tatu}}’s cover of ''“How Soon Is Now.”''
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** In the Season 2 finale, Blair makes a joke about Chuck being spotted in France, Germany and Italy on the Gossip Girl Website after which she says "I hope he has so much fun that they have to quarantine him." Considering the Coronavirus outbreak of 2020 which hit Italy, France and Germany the most, this joke takes a much darker turn.

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** Blair's repeated conflict between her mother has some unfortunate parallels with Leighton Meester's real-life troubles with her own mother. A very public legal battle erupted between them when it was discovered that Leighton was paying her mother $7500 a month for her brother's medical care (as he had just had brain surgery) but it was discovered the money was being spent on cosmetic surgery and other beauty treatments.



* UnfortunateImplications: The show tries very hard to downplay Jack Bass attempting to rape Lily in season 2, but the audience never forgets. So when Chuck [[spoiler:sets Blair up to sleep with Jack in exchange for his hotel]], he is not only [[spoiler:expecting her to prostitute herself]], but also [[spoiler:placing her in direct danger]].

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* UnfortunateImplications: The show tries very hard to downplay Jack Bass attempting to rape Lily UnnecessaryMakeover: There's Chuck's odd choice of hairstyle in season Season 2, but the audience never forgets. So when Chuck [[spoiler:sets Blair up to sleep with Jack in exchange which does nothing for his hotel]], he is not only [[spoiler:expecting her to prostitute herself]], but also [[spoiler:placing her in direct danger]].actor's features.
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this was a relic of an earlier time - in the existing gg fandom today the most popular serena pairings are still derena and serenate, with carter/serena barely having been a blip on the radar


** As of the season 3 premiere, ''a lot'' of people prefer Carter/Serena over any other Serena pairings, ''including'' the original alpha couple.
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** Dan. The one genuinely nice guy on the show, or a misogynistic hypocrite [[spoiler:and with the reveal that he is Gossip Girl, stalker]]?

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** Dan. The one genuinely nice guy on the show, or a misogynistic hypocrite [[spoiler:and [[spoiler:(and with the reveal that he is Gossip Girl, stalker]]?stalker)]]?



** Rufus and [[AsHerself Lisa Loeb.]], Worst of all, [[spoiler: it's Canon!]]

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** Rufus and [[AsHerself Lisa Loeb.]], ]] Worst of all, [[spoiler: it's Canon!]]
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** Matthew Settle and Kelly Rutherford, who play Rufus and Lily, have also gotten this treatment.
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** Many people stopped shipping Derena after it was revealed they shared a sibling, despite the two of them not actually being related. Most fans who stuck around abandoned the ship after the series finale reveals [[spoiler: Dan is Gossip Girl, who had been particularly cruel to Serena.]]

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** Many people stopped shipping Derena after it was revealed they shared a sibling, despite the two of them not actually being related. Most A lot of fans who stuck around also abandoned the ship after the series finale reveals [[spoiler: Dan is Gossip Girl, who had been particularly cruel to Serena.]]
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** Other examples include Derena (Dan/Serena) and Nair (Nate/Blair), Serenate (Serena/Nate), Nenny (Nate/Jenny) and Rufly (Rufus/Lily).

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** Other examples include Derena (Dan/Serena) and (Dan/Serena), Nair (Nate/Blair), Serenate (Serena/Nate), Nenny (Nate/Jenny) and Rufly (Rufus/Lily).

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* OneTruePairing:
** Still Chuck and Blair for some fans.
** Some have jumped to Dan/Blair, as it's free from the whole step-siblings issues that the Dan/Serena ship has, and well, Dan hasn't whored out Blair yet. Not that he's treated her well either. Intentionally ruining her wedding to Louis and letting Chuck take the blame, for instance.

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* OneTruePairing:
**
OneTruePairing: Still Chuck and Blair for some fans.
** Some have jumped to Dan/Blair, as it's free from
many fans, although not everyone was happy with the whole step-siblings issues that the Dan/Serena ship has, and well, Dan hasn't whored out Blair yet. Not that he's treated her well either. Intentionally ruining her wedding to Louis and letting Chuck take the blame, for instance.way it developed (see AbandonShipping).



** Most common is Chair (Chuck and Blair).
** Gossip Girl [[spoiler: him]]self likes to call them Waldass. Never caught on with the fans.
** Other examples include Darena (Dan/Serena) and Nair or Blate (Nate/Blair).
** Serenate (Serena/Nate).

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** Most common is Chair (Chuck and Blair).
**
Blair). Gossip Girl [[spoiler: him]]self likes to call them Waldass. Never Waldass, though that never caught on with the fans.
** Other examples include Darena Derena (Dan/Serena) and Nair or Blate (Nate/Blair).
**
(Nate/Blair), Serenate (Serena/Nate).(Serena/Nate), Nenny (Nate/Jenny) and Rufly (Rufus/Lily).



** Chair has been used as both a positive name or a negative one with gifs of broken chairs or people throwing them.



** Cheath. Shipping Chuck and Chuck being killed. Which apparently some of the actors support.



* ReplacementScrappy: Anyone who likes Jenny, will likely despise Ivy because she seemed to be a lame attempt to hide the fact that Creator/TaylorMomsen didn't want to be on the show anymore. Ivy tends to be ignored or outright erased in fanfiction.

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* ReplacementScrappy: Anyone who likes Jenny, Jenny will likely despise Ivy because she seemed to be a lame attempt to hide the fact that Creator/TaylorMomsen didn't want to be on the show anymore. Ivy tends to be ignored or outright erased in fanfiction.



** People who ship Chair (Chuck and Blair) tend to be positive of a Serenate (Serena and Nate) pairing since it for one keeps Nate away from Blair and for another means the NJBC is nicely paired off. Dan/Blair fans seem to convenience ship Serena/Nate as well, although some seem to ship Nate/Jenny and [[PairTheSpares pair]] Serena with Carter [[DieForOurShip if anyone]].
** People going with the canon finale seem to ship Chuck and Blair, Dan and Serena, Nate and Jenny (who are believed to have HookedUpAfterwards).

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** People who ship Chair (Chuck and Blair) tend to be positive of a Serenate (Serena and Nate) pairing since it for one keeps Nate away from Blair and for another means the NJBC is nicely paired off. Dan/Blair fans seem to convenience ship convenience-ship Serena/Nate as well, although some seem to ship Nate/Jenny and [[PairTheSpares pair]] Serena with Carter [[DieForOurShip if anyone]].
** People going with the canon finale seem to ship Chuck and Blair, Dan and Serena, and Nate and Jenny (who are believed to have HookedUpAfterwards).



** There also seems to be a great deal of warring between fans who believe Nate belongs with Serena and those who believe he belongs with Jenny, even though there hasn't been much on the show itself to support the latter pairing.
** Chuck/Blair fans vs the emergent Dan/Blair ship in Season 4. Blair+Dan is either a chance for both characters to be truly happy with someone they understand, or a narrowly-dodged bullet that would have killed it.

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** There also seems to be a great deal of warring between fans who believe Nate belongs with Serena and those who believe he belongs with Jenny, even though there hasn't been much on the show itself to support the latter pairing.
Jenny.
** Chuck/Blair fans vs the emergent Dan/Blair ship in Season 4. Blair+Dan Dair is either a chance for both characters to be truly happy with someone they understand, or a narrowly-dodged bullet that would have killed it.



* StrangledByTheRedString: After a few regroups it's difficult to name a couple which isn't accused of this by at least some of the fans. Dan/Serena and anything involving [[TheScrappy Vanessa]] get it probably the most.

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* StrangledByTheRedString: After a few regroups it's difficult to name a couple which isn't accused of this by at least some of the fans. Dan/Serena and anything involving [[TheScrappy Vanessa]] get it probably get it the most.



** Chair and Serenate.



** Dan and Nelly Yuki, intellectual outsiders. It helps that Nelly has had a crush on Dan for years.
* TheyWastedAPerfectlyGoodPlot: Serena's StartOfDarkness as Gossip Girl last for a single episode before the real Gossip Girl demands her site back.
%%* UnfortunateImplications: The show tries very hard to downplay Jack Bass attempting to rape Lily in season 2, but the audience never forgets. So when Chuck [[spoiler:sets Blair up to sleep with Jack in exchange for his hotel]], he is not only [[spoiler:allowing her to prostitute herself]], he is also [[spoiler:placing her in danger of getting raped]] according to the majority of viewers.

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** Dan and Nelly Yuki, Yuki are both intellectual outsiders. It helps that Nelly has had a crush on Dan for years.
* TheyWastedAPerfectlyGoodPlot: Serena's StartOfDarkness as Gossip Girl last lasts for a single episode before the real Gossip Girl demands her site back.
%%* * UnfortunateImplications: The show tries very hard to downplay Jack Bass attempting to rape Lily in season 2, but the audience never forgets. So when Chuck [[spoiler:sets Blair up to sleep with Jack in exchange for his hotel]], he is not only [[spoiler:allowing [[spoiler:expecting her to prostitute herself]], he is but also [[spoiler:placing her in danger of getting raped]] according to the majority of viewers.direct danger]].



** Dan when he's trying to write a story about Chuck. Yes of course, bring along the to-do list spelling out just how he plans to use Chuck so the latter can conveniently find it later.

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** Dan when he's trying to write a story about Chuck. Yes Yes, of course, bring along the to-do list spelling out just how he plans to use Chuck so the latter can conveniently find it later.



** Serena spends months doing everything she can to get her father's attention. Most of it consists of getting paparazzi to take pictures of her partying like crazy, appearing topless and sleeping around. Then when her father does appear she doesn't want him to know about her wild past, and pretends like the craziest thing she's ever done is take part in a coco drinking contest. Only to Serena (and possibly Nate) could that make any logical sense.
** In the last season, Rufus dating a con artist and Serena keeping on her cellphone a sextape of her and Dan, ''and'' handing said telephone indirecly to ''Georgina Devilspawn Sparks'' without a second thought. Really, don't they ever learn anything ?

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** Serena spends months doing everything she can to get her father's attention. Most of it consists of getting paparazzi to take pictures of her partying like crazy, appearing topless and sleeping around. Then when her father does appear she doesn't want him to know about her wild past, and pretends like the craziest thing she's ever done is take part in a coco cocoa drinking contest. Only to Serena (and possibly Nate) could that make any logical sense.
** In the last season, Rufus dating a con artist artist, and Serena keeping on her cellphone a sextape sex tape of her and Dan, Dan on her phone, ''and'' handing said telephone indirecly phone indirectly to ''Georgina Devilspawn Sparks'' without a second thought. Really, don't they ever learn anything ?



** Blair to Chuck, at least before his CharacterDevelopment kicked in (and a lot of fans started wondering why would ''he'' have so much patience for ''her''). He ruined her life and relationships several times, stood her up at the airport, slept with a girl she hated the same night when he proposed to Blair, and, well, ''whored her out''. Granted, she wasn't exactly an angel to him, but forgiving the last of the mentioned events should be difficult to imagine in any scenario. Yet Blair does forgive Chuck in a couple of the episodes and [[FelonyMisdemeanor has a longer lasting problem with him taking Jenny's V-card]].
** Why did Lily supposedly [[spoiler:remarry William at the end]]? Fake cancer, anyone? Making a baby with ''her own sister'' while he'd been still married to Lily? [[spoiler:Using ruthlessly his impostor daughter/her impostor niece, who was in love with him, to get back with Lily?]] Ok, Lily [[ManipulativeBitch wouldn't probably have a problem with the last one]], but the "con" column should be pretty loaded even for as calculative woman as her.
** Serena and Dan after you-know-what revelation. Funnily, this case is both the most absurd and the most in-character - after some {{Flanderization}} Serena's become exactly the kind of person who would accept any declared "big wuv" regardless of [[StalkingIsLove implications]].
** A non-romantic (or only half-romantic) example with the gang vs. Jenny and Vanessa in Season 4. Juliet points to Vanessa, that while [[GetOutOfJailFreeCard Jenny sooner or later would always be forgiven because she's family]], the gang has no reason to do the same for Vanessa. And indeed, even Dan disowns her.

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** Blair to Chuck, at least before his CharacterDevelopment kicked in (and a lot of fans started wondering why would ''he'' have so much patience for ''her'').in. He ruined her life and relationships several times, stood her up at the airport, slept with a girl she hated the same night when he proposed to Blair, and, well, ''whored her out''. Granted, she wasn't exactly an angel to him, but forgiving the last of the mentioned events should be difficult to imagine in any scenario. Yet Blair does forgive Chuck in a couple of the episodes and [[FelonyMisdemeanor has a longer lasting problem with him taking Jenny's V-card]].
** Why did Lily supposedly [[spoiler:remarry William at the end]]? Fake cancer, anyone? Making a baby with ''her own sister'' while he'd been he was still married to Lily? [[spoiler:Using ruthlessly [[spoiler:Ruthlessly using his impostor daughter/her impostor niece, who was in love with him, to get back with Lily?]] Ok, Okay, Lily [[ManipulativeBitch wouldn't probably might not have a problem with the last one]], but the "con" column should be pretty loaded even for as calculative calculating a woman as her.
** Serena and Dan after you-know-what revelation.[[spoiler:it's revealed that Dan is Gossip Girl]]. Funnily, this case is both the most absurd and the most in-character - after some {{Flanderization}} Serena's become exactly the kind of person who would accept any declared "big wuv" regardless of [[StalkingIsLove implications]].
** A non-romantic (or only half-romantic) semi-romantic) example with the gang vs. Jenny and Vanessa in Season 4. Juliet points out to Vanessa, Vanessa that while [[GetOutOfJailFreeCard Jenny sooner or later would always be forgiven sooner or later because she's family]], the gang has no reason to do the same for Vanessa. And indeed, even Dan disowns her.

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