In Gossip Girl, the characters are prone to doing some pretty awful deeds. Even the purest of characters become warped by the Upper East Side, involving themselves in awful scandals and victimizing other people to make themselves look good. With that being said, there is the occasional selfless deed committed too.
The characters are a mixed bag, and yet despite them all doing good and bad things, fans take strong, opposing opinions on many. Some are loved despite their awful deeds; some are hated despite their good ones.
Updated on December 1st, 2022 by Aya Tsintziras:
With the HBO Max reboot of Gossip Girl, fans of the original series have a new cast of characters to love or hate. Just like on the OG show, some characters are likable and others seem to scheme too much. The original Gossip Girl series has many characters who viewers love right away and who they continue to root for. At the same time. there are some people on the Upper East Side who seem to have bad intentions, and they don’t treat others very nicely.
Gossip Girl Characters Fans Can’t Stand
Lily Van Der Woodsen
Lily Van Der Woodsen didn’t grow up in a house full of love and compassion, but she doesn’t seem to want to change that about her own family. Lily is a tough character to like because she isn’t always there for her kids Eric and Serena.
While some characters in the series redeem themselves and realize their mistakes, Lily isn’t really like that. Lily often seems to only care about getting married again, and it’s tough to like a character who is very self-centered. Lily thinks too much about things that don’t really matter in life, including fancy clothes and having an even fancier place to live.
Olivia is a college student who appears in season 3, and she also happens to be a famous actor who tries to hide that from everyone. There isn’t a lot to love about the character, who seems to have a hidden agenda at all times. When Dan and Olivia start dating, it’s tough to want things to work out between them.
In one episode, Olivia insults Dan when she goes on The Tonight Show Starring Jimmy Fallon and makes fun of him. This leads to people laughing at Dan and referring to Dan as “Bathroom Boy,” which is humiliating.
Carter is more of a minor character who is only in a few seasons, but he makes an impression that isn’t very positive. At the beginning of season 3, fans find out that Carter and Serena went on vacation together. Carter is wealthy, conceited, and often very mysterious. But he isn’t very layered.
Carter isn’t honest about his intentions, and he doesn’t like to talk about his feelings. This makes it impossible to like him very much or want him to succeed. When he leaves the series, he isn’t missed thanks to the drama that he causes everywhere.
While Blair’s mother Eleanor makes the smart choice to marry Cyrus, who is sweet and wonderful, Eleanor herself has some lost time to make up for with her daughter. Eleanor doesn’t seem to notice how hurt Blair is that she feels like her parents don’t love her or want to hang out with her.
Although Eleanor and Blair do have some nicer scenes by the end of Gossip Girl, it still feels like the damage has been done. Blair needs to have a parental figure who is around much more, especially during her teenage years, and Eleanor doesn’t do that.
When Ivy first joins the series, it’s while masquerading as Charlie, an extended member of the Rhodes family, and Serena’s cousin. She fits in well enough at first, but once everyone discovers that she was hired to pretend to be Charlie, literally everyone turns on her. Instead of trying to take the high ground, Ivy becomes more and more manipulative.
It’s also a little odd to fans that she dates both Dan and Serena’s fathers during her attempts to manipulate the Van der Woodsens. That alone was enough to weird fans out since she’s the same age as Serena, Blair, and her friends.
It’s often the younger generation of characters that are seen as the most problematic of the Gossip Girl bunch, but Bart Bass is actually the worst. He’s easily the most callous and manipulative of the series.
The silver lining is that Bart’s behavior, and just how he treats his son, goes a long way to explain just how Chuck becomes who he is as a teenager. As much as fans hate Bart, his presence in the series allows Chuck a little more empathy from the viewers.
Louis Grimaldi seems like the ultimate fairy tale prince. He’s the answer to all of Blair’s romantic questions – until he reveals his true colors to her. When looking at Blair’s boyfriends on Gossip Girl, Louis stands out since he’s royalty, and that makes him a more compelling character, at least at first.
It’s an unwritten rule in the Gossip Girl handbook that if a character hurts Blair Waldorf, the audience is going to hold a grudge. His attempt to lock Blair into a loveless marriage and a hostile family is one the audience will never forgive.
Jenny starts off as one of the purest characters. She’s from Brooklyn, with very little to do with the riches and glamour of the Upper East Side.
Yet she quickly gets dragged into the world and becomes as vicious as Blair Waldorf herself, going as far as to get herself involved in a scheme that gets Serena drugged. Still — Jenny objectively isn’t the worst character on Gossip Girl, but there is a definite air that she doesn’t belong, so fans tend to latch on harder to her wrong-doings, and she gets a harsher time of it than characters such as Blair might. She also caused problems between the iconic power couple of Blair, and Chuck and even though this was mostly Chuck’s fault, ship stans weren’t happy.
Vanessa also comes from a place that isn’t the Upper East Side, and she has very little to do with the riches and scandals of the world that Gossip Girl reports on. Yet she quickly goes in the same direction as Jenny and is also involved in the scenario that has Serena drugged.
Worse, she goes on to lie about it and place all the blame on Jenny. The world she’s entered has turned her into a monster, and fans have little sympathy. It’s definitely hard to like Vanessa after watching her make certain choices throughout the show’s six seasons.
Dan starts out as one of the least problematic guys. Hailing from Brooklyn, starry-eyed over Serena, he wants to do good by everyone. The last season reveals that he’s been Gossip Girl all along, which caused an understandable storm with fans when it was first aired — especially as Dan is so very quickly forgiven by the other characters, leaving the viewers craving revenge that the other characters aren’t.
Fans were shocked when Dan was said to be the one behind these harsh rumors and stressful posts over the years. This changes how viewers see the character and makes it hard to feel like he’s one of the sweetest people in the series.
Juliet is a troubled woman who enters the series in season 4 and causes a world of problems. She manipulates the characters and is unapologetic, going as ruthlessly far as to almost kill Serena.
She genuinely doesn’t seem to care about other people and because of this, fans have little sympathy for her troubled past. Gossip Girl is definitely a fun show with a fast pace and lots of obstacles being thrown in the characters’ paths. But characters like Juliet become a bit tiresome to watch after a while because they have such negative intentions.
Georgina Sparks is a friend of Serena from her wild days, only she hasn’t quite recovered from them. She blackmails Serena, pretends to be someone else entirely, and even tricks Dan into thinking that her half-Russian baby is actually his, forcing him to look after Milo for quite a while.
She’s a genuinely repulsive person and fans never quite forgave her for the trouble she causes the well-loved characters over the course of the series. Georgina always has some kind of plan that she’s working on, and that makes it tough to want the best for her.
Most Likable Gossip Girl Characters
Rufus is one of the most likable Gossip Girl characters from the start. He cares about his kids and tries to give them the best of everything, even though he doesn’t have the kind of money that their classmates do.
Rufus is given a detailed backstory and a lot of current personal drama as well. It’s always juicy and entertaining watching Lily and Rufus together, as they have feelings for each other but never quite make things work between them. Rufus is more invested in being a good parent than some other adults on the show, which is what makes him so endearing.
Nelly goes to school with Blair and Serena in season 1 and is shown to be an intelligent and compelling character. She and Blair are super competitive with each other, which proves that Blair needs to stop scheming so much and learn to enjoy her life and be happy.
Nelly is one of the smartest Gossip Girl characters, and fans don’t get to see that much of her after a while, which is too bad. Nelly wants to do well in school and in life, and it’s nice to see a character following their dreams.
A lot of the parental figures in Gossip Girl can be just as manipulative as the teenagers. One of the few to always remain supportive and kind is Blair’s stepfather, Cyrus Rose.
He doesn’t appear often in the series, but when he does, it’s clear that he makes Eleanor a kinder woman, and that he genuinely cares about the Waldorf women. Cyrus is probably one of the best people in Blair’s life, and it’s a shame she doesn’t get to spend more time with him. Cyrus doesn’t scheme or plan to hurt other people like some others do.
Eric Van der Woodsen
Eric might be the only Upper East Sider to not be touched by the darkness associated with Gossip Girl’s blasts. He’s a good guy when the series starts, one bogged down by his own self-doubts and emotional issues. Eric becomes fast friends with Jenny, and always wants to do the right thing.
There’s no backstabbing from Eric, and he cuts ties with the drama as soon as he can. The audience loves him for his commitment to being good, even if he’s not the most entertaining of the bunch.
Chuck starts out as one of the most despicable characters in the show. He assaults both Serena and Jenny very early on, seeming to care about nothing except his money and ego. After the first few episodes, it seems a safe bet that he’ll be the most hated antagonist in the show.
Yet, the show later plays on his upbringing and neglect to encourage fans to like him, going as far as to explore his deep relationship with Blair to make people sympathize. Although the assault is brought up again, Chuck apologizes. In real life, someone who had done these awful things wouldn’t be so easily forgiven — rightfully so. Yet, the way the show later paints Chuck endears him to fans, whether rightly or wrongly.
Blair Waldorf is vicious and ice-cold, but at least she’s aware of it. Unlike some of the other characters, she doesn’t try to hide who she is. It doesn’t make her a nice person, but it certainly makes her an interesting one. Although Blair can be truly horrible and ruled her high school with the iron fist of the worst bully of New York City, she’ll also go to extreme lengths to protect her friends.
Her more vulnerable side is also brought out with Chuck which, problematic as he is, definitely endears viewers to Blair a little and shows them that she has a heart. Blair is easy to like because viewers understand who she is.
Although Nate is an inherent part of the world that causes so much hurt, he’s probably the least problematic guy in it. He tries to treat women with respect, and although he hasn’t always been perfect, he at least makes the effort to be a loyal friend.
His family problems have him acting out at multiple points through the series, and he also cheats on Blair with Serena, so he’s far from perfect — but he does well enough to come out relatively unscathed in the eyes of fans. Quite a feat in this series.
Dorota works for Blair’s family, and she is a woman from Poland who is loyal to Blair even through her worst times. At her own wedding when Blair breaks down over Chuck, she takes the time out of her own happy day to assure Blair that she wants her to be happy above all else.
She’s the one character who never engages in acts of betrayal like other Gossip Girl characters. Dorota is a genuinely sweet woman with a heart of gold, and she deserves the best. She’s sweet to watch from her very first few appearances and viewers are always happy to see her.
Serena Van Der Woodsen
Serena is someone who’s had quite a history. She’s hurt other people, starting out the series having slept with her best friend’s boyfriend, but she’s determined to make amends and Serena spends Gossip Girl being loyal to Blair.
Although she’s far from perfect, it’s abundantly clear that she genuinely regrets the things she’s done in her past and is trying to be a better person. For the most part, she succeeds. It’s easy to like both Serena and Blair and cheer for them, wanting them to learn lessons and become better people by the end of the series, which is what happens.