In the show 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 May 3oth, 2021 by Amanda Bruce: One of the great things about a series like Gossip Girl is that the characters can make the audience alternately love them and hate them, sometimes in the same episode. Someone like Chuck Bass can be despicable and a sweetheart. Just which characters fans tend to like the most often comes down to whether they’re seen as redeemable – or just how entertaining they are for the audience. Gossip Girl features a healthy dose of both. Those characters the audience just can’t stand tend to overstay their welcome or hurt the most liked characters.
15 Fans Can’t Stand: Ivy Dickens
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.
14 Likable: Cyrus Rose
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.
13 Fans Can’t Stand: Bart Bass
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.
12 Likable: 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.
11 Fans Can’t Stand: Louis Grimaldi
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.
It’s an unwritten rule in the Gossip Girl handbook that if you’re a character that 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.
10 Likable: Chuck Bass
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.
9 Fans Can’t Stand: Jenny Humphrey
Jenny starts off as one of the purest characters. She’s from Brooklyn, with very little to do with the riches and glamor 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 in the series, 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.
8 Likable: Blair Waldorf
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 the man is, definitely endears viewers to Blair a little and shows them that she has a heart.
7 Fans Can’t Stand: Vanessa Abrams
Vanessa also comes from a place that isn’t the Upper East Side, and 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 of the blame on Jenny. The world she’s entered has turned her into a monster, and fans have little sympathy.
6 Likable: Nate Archibald
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.
5 Fans Can’t Stand: Dan Humphrey
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.
4 Likable: Darota Kishlovsky
Darota works for Blair’s family, 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 betrayals. Dorota a genuinely sweet woman with a heart of gold, and she deserves the best.
3 Fans Can’t Stand: Juliet Sharp
Juliet is a troubled woman who enters the series in season four 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.
2 Likable: 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 the series doing that by being incredibly 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.
1 Fans Can’t Stand: Georgina Sparks
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.
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