YMMV / Gossip Girl (2007)

aka: Gossip Girl

• Abandon Shipping:
  • Chuck/Blair (aka "Chair") steadily lost fans from the start of season 3. Chuck whoring Blair out to his uncle Jack in "Inglourious Bassterds" really put a vast number of people off the once golden couple of the show. Chuck taking Jenny's virginity, hiding it from Blair and then trying to propose to Blair on the same night was another not so glorious moment for the pairing. It was definitely a Broken Base though, as there were still hordes of die hard shippers of the pairing. There are also the people who jumped ship from all Chuck pairings after the allegations against Ed Westwick
  • Many people stopped shipping Derena after it was revealed they shared a sibling, despite the two of them not actually being related. A lot of fans who stuck around also abandoned the ship after the series finale reveals Dan is Gossip Girl, who had been particularly cruel to Serena.
• Actor Shipping:
  • Ed Westwick and Leighton Meester had quite the following, most of it on LiveJournal. Jessica Szohr, who was dating Westwick at the time, got the Die for Our Ship treatment. Of course, it doesn't help matters that there is a video up on YouTube where 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 Blake Lively got practically none of this.
• Adaptation Displacement: If you hear somebody talking about Gossip Girl, there's a pretty good chance they're talking about the show, not the books.
• Alternate Character Interpretation:
  • Blair and Serena whenever they are in an argument. Half of the fans will consider Blair an immature, self-absorbed bitch and Serena wronged and misunderstood, while the other half feel Serena is the bitch and Blair is misunderstood.
  • Chuck. Heroic great guy who's just been acting out to get attention from his not-too-loving father, or villainous sociopathic pseudo-rapist, depending on who you ask.
  • Louis talking to Blair during their wedding dance. Showing his true colors? Or has he been broken by the Upper East Side and has become like them? Or someone who still loves Blair enough to say the only thing he could think of to make her run away to cancel the wedding?
    • Since he forced her to remain married to him by threatening to bankrupt her family, we can in fact conclude that he is simply a Jerkass of epic proportions.
  • Rufus, nice liberal dad, or weakling that allowed the situation with Jenny in the second season to balloon out of control by failing to set proper boundaries?
  • Dan. The one genuinely nice guy on the show, or a misogynistic hypocrite (and with the reveal that he is Gossip Girl, stalker)?
  • In "Hi, Society" (1.10) does Cece really try to break up Dan and Serena? Or does she use Reverse Psychology to bring about the opposite result?
• Anvilicious: Chuck and Blair belong together. Anyone foolish enough to doubt this will be hit over the head with it on a regular basis.
• Ass Pull:
  • Nate's reappearing love for Serena in season three and, a few episodes later, Serena's very sudden love for Nate.
  • The reactivation of feelings between Serena and Dan in the last episodes of season 3.
  • The reveal of Gossip Girl's identity is seen by some fans to be this, considering some of the events of the early seasons such as Blair continually humiliating Jenny, and some timing discrepancies.
• Awesome Music:
  • Sum 41's "With Me" in the infamous limo scene.
  • The Kills' "URA Fever" playing as Serena infamously declares, "I killed someone." Too bad it ended up being the lamest 'death' possible by accidental overdose
  • Bloc Party's "Signs" at the end of "Oh Brother Where Bart Thou"
  • Turin Break's "Dark on Fire" at the end of "Pret-A-Poor-J"
  • The Virgins' "One Week of Danger" playing the morning after the limo scene
  • Death Cab for Cutie's "The Ice Is Getting Thinner" in the season one finale
    • Given that it's a Josh Schwartz show, DCFC is pretty standard fare.
  • "Shove it" by Santigold during the climax of 'The Ex Files'
• Badass Decay: Blair, in season 5
• Big-Lipped Alligator Moment: Arguably Chuck's attempted rape of Serena in the pilot. By episode two, both seem to have forgotten all about it. Could also be an example of Characterization Marches On.
  • Likely also a result of retooling after the Pilot Episode. The original intention was likely to position Chuck as the antagonist rather than an anti-hero protagonist.
• Broken Base:
  • 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 favor, 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.
  • 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.
• Cargo Ship: Chuck and his scarf.
• Crack Ship:
  • Dan and Nelly Yuki.
  • Rufus and Lisa Loeb. Worst of all, it's Canon!
  • Some feel this way about Lily and William back together in the finale.
• Creator's Pet:
  • Vanessa, according to some. The vast majority of the fans loathe her and any episode she doesn't appear in is immediately hailed as being much better for her not being in it. Yet she keeps getting storylines, is the only girl who has been romantically linked to all male leads (at least until Blair caught up with her) and is constantly talked about as being a great person with high morals even though she behaves just as badly as Blair, Jenny and Serena. On the other hand, she is the only main character who is missing from several episodes each season, and while she gets storylines, most of them directly involve one or more other main characters.
  • Dan is a self admitted example. According to the showrunner Josh Safran, he saw a lot of himself in Dan and wanted him to be popular because of it. He even admitted to breaking up Chuck and Blair just so Blair could be with Dan instead.
  • Chuck, probably because he's the wish fulfillment type that does shady things and gets away with it while having the main female character fall for him to add towards the man fantasy sex machine wankage.
• Die for Our Ship:
  • A rare instance of the show itself playing into this trope - Bart Bass seemed to be killed off at least in part to allow Lily and Rufus to become an Official Couple, given how quickly the latter happened after the former.
  • Elle, Chuck's two-episode season two crush, earns this treatment from the Chair fans. Those who even admit to her existence in the first place, that is.
  • Eva... Hooo boy...
  • Dan and Blair... ehem Though not even official, the minions established shippers are already on the attack.
  • Later, both Chuck and Serena seem to get the treatment from Dair fans.
  • Jenny gets this from both Serenate fans and Chair fans.
  • Vanessa from... pretty much everyone.
  • In the long run Rufus/Lily seems to be put down for the sake of Dan/Serena not being step-siblings anymore.
• Draco in Leather Pants: Chuck. Blair as well. Blair bullying and abusing most of her school and generally manipulating and mistreating her friends? Badass! Another (usually female) committing the heinous crime of not bowing down to Blair's will? What a monster!
• Escapist Character: Serena in the books. She's a wealthy teenage girl who's absolutely gorgeous, has boys worshipping the ground she walks on, regularly hangs out with celebrities, and gets accepted into the most prestigious universities. She gets access to all of these with little to no effort.
• Esoteric Happy Ending: Despite the ridiculous flashforward it's hard to see the end of the show as anything but this.
  • Dan is revealed as Gossip Girl, and his reasons being he wanted to "write himself into Serena's life". Thus making him a sociopath stalker who jeopardized the main characters' lives on multiple occasions and repeatedly ruined their lives.
  • Serena is somehow happy with this. He did it out of love after all.
  • Chuck allows his father Bart to die by letting him fall off a roof.
  • Blair is on the roof when Bart died. She does achieve her goal of becoming the 'powerful woman' she wanted to become after finally finding a way to be successful in her mother's business (which itself would leave a stain of nepotism on her achievements in the view of the outside world). But she never gives up on scheming even after realizing she needs to grow up.
  • Nate has started down the path of fraud just like his father, and is only rescued when Bart dies. His possible bid for mayor is also pretty random.
  • Lily is back together with William, apparently ignoring what happened in the third season.
• Ensemble Dark Horse:
  • Dorota, Eric, Georgina and Carter all qualify, as all of them are extremely popular among the fans (even more popular than some main characters), despite being only recurring or guest starts, to the extent that all have come to play a bigger role as the show has progressed.
  • Let's not forget Chuck Bass, who was originally supposed to be a guest character and who assaulted two of the female characters in the pilot. Now he and Blair are king and queen of the show.
  • Cyrus Rose, full stop.
  • Lola Rhodes, who is memorable for being one of Nate’s best girlfriend, the Only Sane Woman, and for not succumbing to the influence of the UES unlike other characters (Jenny, Vanessa).
• Estrogen Brigade: Yes, the show is targeted towards girls, but tons of them come just to Squee over the hot male actors. 'Nuff said.
• Fanon:
  • It's almost universally agreed by fans that Blair slept with Jack Bass at New Years so that he would agree to go and find Chuck. There is nothing in the show that hints to this being true.
  • In the finale, Dan is revealed to be Gossip Girl and Jenny knew the secret, but in fanfiction it's starting to become agreed on that they worked together
  • Nate and Jenny will pretty much always get together in any story pertaining to the 5 year timeskip
• Fanon Discontinuity:
  • The "Eyes Wide Shut" storyline in season two, which most fans ignore completely.
  • Everything that points to Elizabeth Fisher being Chuck's biological mother.
  • Many fans (especially Dair fans) like to pretend season 6 as a whole doesn't exist.
• Fan-Preferred Couple:
  • In the early episodes of the first season many fans preferred the combo Chuck/Blair-Nate/Serena-Dan/Vanessa to the then Official Couples 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.
  • Dan/Blair has gotten a following which almost rivals the Chuck/Blair ship.
  • Rufus/Lily has proven to stand the test of time as a fan-favorite pairing, with many fans being very unhappy that the pair were broken up to accommodate Dan/Serena, a ship which by that point had worn out its welcome for many people.
• Harsher in Hindsight:
  • Re-watching Season 1's episode Dare Devil, where Jenny emphatically tells Dan she won't forget who she is just because she's hanging out with Blair and her Girl Posse can be this, if you know just what's gonna happen to her during that season. And the season that follows. And the third one. Especially the third one.
  • Chuck's attempted rape of Serena in the pilot gets forgotten about. In 2017 actress Kristina Cohen claimed that Ed Westwick had brutally raped her.
  • Harvey Weinstein is mentioned positively as one of the figures interested in Dan's book's movie adaptation, with Dan's literary agent saying that an Oscar wouldn't be a faraway dream. Cut to 2017, Weinstein would become a pariah in Hollywood due to sexual abuse allegations.
  • All of those times Gossip Girl has ruthlessly and mirthfully mused about Jenny being in a situation where she was soon to be raped, and in general crossing several lines when talking about Jenny in sexual situations? That's Dan. Some big brother he is...
  • 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.
  • 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 rest of the world), this joke takes a much darker turn.
• Heartwarming in Hindsight: Eric and Jonathan’s breakup during the season felt tragic. However… Gossip Girl (2021) revealed that they are happily married.
• Hilarious in Hindsight:
  • Not exactly hindsight but in season four Blair dates a prince and the designated roadblock between them is that she's a commoner and he is heir to the throne. It's pretty much taken for granted that a royal prince could never marry a commoner. Probably was a safe bet when the episodes were written. But the episode in which it is brought up aired mere days before heir to the British throne Prince William married commoner Kate Middleton amidst a media frenzy spectacle and the union was celebrated by pretty much everyone everywhere, including William's family members.
  • Blair's nickname Queen B after she becomes a princess
  • 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.
  • The name of the site (and the show) after Gossip G.I.R.L. is revealed to be Dan Humphrey.
  • The scene from the finale where Rachel Bilson is auditioning for Blair in the adaptation of Dan's book becomes funny when Leighton Meester started dating (and eventually married) Adam Brody.
  • In the pilot, Serena suggests that Jenny would look better in a black, which eventually became Jenny's favorite color.
  • After Leighton Meester played one of society's elite whose every word and fashion choice becomes a trend, in Making History (2017) she plays a Fish out of Temporal Water who's constantly fascinated by the most mundane aspects of modern culture.
• Ho Yay: In the first season, Nate sleeps at Chuck's an awful lot. Blair and Serena have their moments, too.
  • Chuck and Nate live together as of 3.09, so those sleepovers live on!
    • Apparently their actors are a real life example.
  • It doesn't help Nate's case that, in the novels, Chuck was bi.
    • That's hinted at during the early episodes - Blair doesn't want to know what Chuck did to get a replacement suit after being stripped naked and locked on a roof.
    • And in a later episode, where Blair tricks Chuck into kissing a guy as part of their "game." His response: "You think that's the first time?"
  • Chuck to Dan in "The Serena Also Rises" - "Are you gay?" A lot of fans wish the answer could be yes, for both of them.
  • It's also heavily implied in the novels (with several scenes that sort of just 'fade to black'— i.e. Blair inviting Serena slyly to join her in the tub when she was living with Vanessa) that Serena and Blair have a physical relationship on top of their friendship. Oh, it's also implied that they're both Gossip Girl.
  • A lot of fans interpret Jenny and Blair this way as well. Her desperate attempts to be Blair's friend in S1 can look a lot like love, and she reveals later that she wanted to be Blair's friend much more than she wanted to be Serena's. There's also Blair's statement at the end of S2: "You're my queen. I choose you..."
  • In the books, Jenny really, really comes off as having a crush on Serena. Supposedly, it's simply an admiration and a desire to be more like Serena, but there are several moments when Jenny's thoughts about Serena directly parallel Dan's, who canonically has a crush on Serena early on in the series.
  • Also in the books, Jenny and a female friend "experiment" with each other sexually. The friend is more into it than Jenny is.
  • 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 t.A.T.u.’s cover of “How Soon Is Now.”
• Jerkass Woobie: Chuck is possibly the most morally ambiguous character of the bunch. At the same time, if something gut-wrenchingly horrible is happening on Gossip Girl, it's a safe bet that it's happening to Chuck.
• Launcher of a Thousand Ships: Serena and Nate, in-universe. Blair in fandom.
• Memetic Mutation:
  • I'm Chuck Bass
  • XOXO
  • Dan Humphrey did everything ever. Won Nationals. Killed Bambi's mother. Is A. Is Veronica Mars. Luke's Father. Ted's Wife.
  • 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 "Go piss Girl".
  • The Thanksgiving dinner scene from season 3's "The Treasure of Serena Madre", featuring Jason Derulo's "Watcha Say" in the background, became such a popular scene on social media that it ended up getting mass parodied on Tik Tok.
  • Serena has to go.
• Mind Game Ship: Chuck and Blair spend a better part of the second season competing over who could invoke this trope the most.
  • This trope is also the reason for Chuck and Blair's season 3 break up.
• Moral Event Horizon:
  • Many viewers feel that "Inglourious Bassterds" is the moment when Chuck Bass crossed the line from.
  • For some, Chuck's behavior in "The Princesses and the Frog" caused him to cross it big time.
  • And in "Touch of Eva," Blair finally sunk to his level.
  • Georgina crossed the line when she deceived Dan Humphrey into thinking she was pregnant with his son. He was there when Milo was born. He spent the summer supporting Georgina and helping her take care of the baby. Then as soon as she didn't need him anymore, she ditched Dan and took Milo out of his life forever. Unlike all of Georgina's previous antics, which revolved around inflicting (albeit excessive) comeuppance for past indiscretions, this was a clear-cut case of exploiting and hurting an innocent person. Specifically, the one person who had always been the first to trust her and give her a second chance.
  • Agnes roofies Jenny and then abandons her at a club surrounded by men having a bachelor party, with the express purpose of getting her raped. Agnes does this as revenge for Jenny contacting potential clients without her behind Agnes’ back back in Season Two— which she already burned Jenny’s dresses and kicked her out for.
• Narm: "The Revengers," specifically the rooftop climax. Even more specifically the hilariously awful scoring from Transcenders as Chuck faces off against Bart with Blair in attendance, and their fight ends with Bart having a Disney Villain Death. Danny Elfman it isn't. It's not even Blake Lively... er, Neely.
• Narm Charm: The dream sequences. The actors are often free to ham it up and chew as much scenery as they want.
• No Such Thing as Bad Publicity: Played straight and subverted.
  • Played straight when Chuck has the cops raid his own pub opening. Also in the next episode, with this comment:
  Chuck: Do you think people go to the Mercer for the maid service? They go to see Russel Crowe throw a hissy.
  • Subverted later in season three when Chuck is accused of sexual harassment and ends up having to sign over his hotel to save it from the bad PR.
  • Played straight by the show itself. When a reviewer called the show: "A parent's worst nightmare" the publicity department put that quote up on huge posters and used it for advertisement.
• One True Pairing: Still Chuck and Blair for many fans, although not everyone was happy with the way it developed (see Abandon Shipping).
• One True Threesome:
  • The show tried to market the Dan/Vanessa/Olivia threesome as such. The fans still didn't like it.
  • Some fans ship Chairenate. That's Chuck, Blair, Serena and Nate together.
• Platonic Writing, Romantic Reading: Nate is often referred to as an older brother figure for Jenny... Until he ends up making out with her. Fast-forward to season 3, and he's back to acting as if he only ever saw her as a little girl. Then why in God's name did you stick your tongue down her throat, dude?
• Portmanteau Couple Name:
  • Most common is Chair (Chuck and Blair). Gossip Girl himself likes to call them Waldass, though that never caught on with the fans.
  • Other examples include Derena (Dan/Serena), Nair (Nate/Blair), Serenate (Serena/Nate), Nenny or Jenate (Nate/Jenny) and Rufly (Rufus/Lily).
  • The Dan/Blair pairing is a rather fun example. Those who ship them tend to call them Dair (as in "we dare to dream") while those who dislike them together tend to call then Blan (as in "they're bland together") or Ban (as in we should Ban them)
  • Not a romantic portmanteau, but the extended Van der Woodsen/Bass/Humphrey family, with Lily's marriages to first Bart and then Rufus, has become the Van der Bassphrey family.
  • Daircut. Shipping Dan and him getting a haircut.
• Replacement Scrappy: Anyone who likes Jenny will likely despise Ivy because she seemed to be a lame attempt to hide the fact that Taylor Momsen didn't want to be on the show anymore. Ivy tends to be ignored or outright erased in fanfiction.
• Rescued from the Scrappy Heap:
  • Happened to Nate in season 3. Fans grew tired of his constant bed-hopping and sheer aimlessness in season 2, so the writers gave him an abundance of family-oriented stories and returned him to his roots by having him be desperately in love with Serena and suddenly interested in his best friend's welfare.
  • For some this happened with Vanessa in season four.
• The Scrappy: Vanessa Abrams, especially true among fans of the books when they watch the series. She got better (a little) in season 2, only to get a lot worse in season 3. In fact, the very same author of the books talks about it. But the producers insist on giving her more stories, in spite of general disapproval. Just visit any Gossip Girl webforums and you'll see rabid comments about Vanessa.
  • As of Season 4, Vanessa has no friends left, among the characters or the viewers. Frustrated with how the NJBC seem to 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. 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.
    • And they got their wish in Season 5. (Although she came Back for the Finale, it was a very brief cameo.)
    • Vanessa still has some fans; everybody hates Sage.
  • Absolutely no one likes Ivy, both in-universe and out.
  • 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 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 Designated Hero at worst. Doesn't help that she's also supposed to be the main character. Key words here being "supposed to be".
• Ship Mates:
  • 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 pair Serena with Carter 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 Hooked Up Afterwards).
• Ship-to-Ship Combat:
  • Fans of the book tend to think Blair belongs with Nate. Fans of the show tend to passionately believe Blair belongs with Chuck. Cue endless arguments.
  • 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.
  • Chuck/Blair fans vs the emergent Dan/Blair ship in Season 4. 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.
• So Bad, It's Good: The poetry Dan writes in the books is just so incredibly awful that it's unbelievably awesome.
• Strangled by the Red String: 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 Vanessa probably get it the most.
• Stoic Woobie: Chuck.
• Super Couple: Chuck and Blair.
• Take That, Scrappy!: Vanessa gets a lot of this, mainly from Blair, who hates her.
  • As of season 4, she's been shipped off to Barcelona.
• Testosterone Brigade: To go along with the aforementioned Estrogen Brigade, the show also had a lot of male fans who watched it for Blake Lively, Leighton Meester, Michelle Trachtenberg, Taylor Momsen ( for teenagers), Kelly Rutherford (for fans of older women and/or Melrose Place)... and that's just the regulars/semi-regulars.
• Theme Pairing:
  • Chuck and Blair are Birds of a Feather, two dark, ruthless people who scheme and manipulate their way to the top but who deeply care for the people close to them.
  • Serena and Nate. A carefree, Brainless Beauty duo, both fickle and free-spirited and neither with any real ability to come up with a cunning plan or with any real drive in their lives. Often compared to a pair of golden retrievers (with Chuck and Blair being their masters).
  • Even Dan/Blair who are both Brainy Brunettes who love posh art and cinema.
  • Dan and Nelly Yuki are both intellectual outsiders. It helps that Nelly has had a crush on Dan for years.
• They Wasted a Perfectly Good Plot: Serena's Start of Darkness as Gossip Girl lasts for a single episode before the real Gossip Girl demands her site back.
• Too Bleak, Stopped Caring: 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.
• Unnecessary Makeover: There's Chuck's odd choice of hairstyle in Season 2, which does nothing for his actor's features.
• Vindicated by History: 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.
• Why Would Anyone Take Him Back?: In spades.
  • Blair to Chuck, at least before his Character Development kicked 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 has a longer lasting problem with him taking Jenny's V-card.
  • Why did Lily supposedly remarry William at the end? Fake cancer, anyone? Making a baby with her own sister while he was still married to Lily? Ruthlessly using his impostor daughter/her impostor niece, who was in love with him, to get back with Lily? Okay, Lily might not have a problem with the last one, but the "con" column should be pretty loaded even for as calculating a woman as her.
  • Serena and Dan after 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 implications.
  • A non-romantic (or only semi-romantic) example with the gang vs. Jenny and Vanessa in Season 4. Juliet points out to Vanessa that while Jenny 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.