Gossip Girl would not be the present that’s if it weren’t for the assorted dramas that rocked the Upper East Side all through its 6 season run. At one level or one other, even essentially the most ethical characters made extreme errors and horrible selections that left lingering repercussions.

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From Blair’s fixed scheming, to Chuck’s debaucherous methods, a number of the worst selections made within the present had malicious and spiteful motivations. However, there have been instances {that a} character’s actions have been merely wayward selections dedicated by means of their very own selfishness, with maybe unpredictable penalties.

9 Vanessa: Scheming With Juliet

nate juliet vanessa gossip girl

When Vanessa elected to group up with Juliet in her revenge plot in opposition to Serena, it did not appear to be the worst of selections she may ever make, however as all the time with Gossip Girl, there was extra to the plan than initially thought. Without Vanessa being totally conscious, Juliet’s plan to take down Serena concerned drugging her at a celebration in “The Witches of Bushwick.”

Her decision-making from there on out solely received worse, as she tried to keep away from taking any blame for Serena being in hospital. In “Gaslit,” quite than admit to Serena’s household and buddies that she had any half within the scheme in opposition to Serena, she selected as a substitute to pin all the blame onto Jenny. For a personality who was often so ethical, her selections on this narrative have been really abysmal.

8 Lily: Getting Ben Sent To Prison

Lily was a sophisticated character, as she principally tried to do proper by her kids, however did not all the time go about it in the fitting means. Her resolution to get Ben despatched to jail is a main instance of this – as revealed within the episode “Townie,” Lily was making an attempt to get Serena accepted into an excellent faculty and preserve their reputations in examine, with out a lot luck.

Upon listening to rumors about Serena’s ‘relationship’ with Ben, Lily determined to make use of the gossip to blackmail the college into letting Serena in. While it wasn’t her preliminary intention for him then to get investigated for an alleged relationship with a minor, she went on to forge Serena’s signature which despatched Ben to jail. It was a sequence of unhealthy selections, that received even worse when she selected to maintain quiet till confronted by Serena, and it was genuinely one of the worst things Lily did.


7 Rufus: Starting A Relationship With Ivy

Rufus Humphrey in Gossip Girl

Throughout Gossip Girl, Rufus was typically the character that others would flip to for assist, as he was very grounded and gave nice recommendation. Yet, that did not cease him from making unhealthy selections every now and then – like in season 6 of the present, when he determined that starting a relationship with Ivy can be a good suggestion.

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While Ivy was admittedly very forthcoming with him, Rufus beginning a relationship together with her was the stupidest resolution he made, and really out of character. Not solely did he assume that Ivy was his niece at one level, however he additionally dated her understanding she had lied and manipulated all of Lily’s household. He knew it was a nasty concept although, when fortunately he got here to his senses and ended the connection.

6 Jenny: Trying To Manipulate Nate

Jenny’s transformation in Gossip Girl noticed her rising from a candy and caring lady to a crafty and egocentric individual, who made a couple of unhealthy resolution. One of the times that made fans hate Jenny essentially the most was her ongoing string of unhealthy selections in season 3, when she relentlessly pursued Nate and meddled in his relationship with Serena.

Despite all the form issues that Nate did for Jenny, she selected to control him and mess along with his relationship, all as a result of she nonetheless had emotions for him. In “Inglourious Bassterds,” Jenny uncared for to inform Nate that Serena was throwing him a shock party, so she may spend the day with him and even kissed him when she knew he did not reciprocate her emotions. And, in “The Unblairable Lightness of Being,” she even hid messages from him and stole one in every of Nate’s shirts to make Serena jealous, even though Nate had been nothing however an excellent good friend to her.

5 Nate: Dating Sage

Nate, for essentially the most half, was one of many few characters on Gossip Girl who was genuinely good, and often had a transparent head when it got here to creating selections. Yet, he tended to have unhealthy judgment when it got here to ladies, and by the present’s ultimate season it appeared that even the resident good man of the Upper East Side would not go unscathed.

Sage was one of Nate’s worst girlfriends, as not solely was she underage once they began their relationship, however she was additionally the daughter of Serena’s boyfriend. The scenario solely received worse when Sage launched Dan and Serena’s intercourse tape in “Monstrous Ball,” and Nate broke up together with her, solely to get again collectively together with her later. Even starting a relationship with Sage was a horrible resolution within the first place, and it solely received worse as time went on.

4 Chuck: Trading Blair For The Hotel

If there was anybody who may break Blair Waldorf’s coronary heart into 1,000,000 items, it could be Chuck. And that is simply what he did in “Inglourious Bassterds,” when, selfishly, he gave permission for Jack to sleep with Blair ought to he signal the rights to the resort over to him. The giving permission a part of that is disturbing, however the truth that Chuck would even put Blair within the scenario within the first place was really horrific.

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Chuck knew that Blair would do something that he requested of her, and but orchestrated this scheme behind her again, pondering that if the reality have been to come back out Blair can be tremendous with it. To make issues worse, when Blair did discover out, it took her breaking down at Dorota’s wedding ceremony and breaking apart with him for him to appreciate the severity of his actions. Chuck made numerous treacherous selections all through Gossip Girl, however this was really his worst.

3 Serena: Making A Sex Tape With Dan

Serena and Dan share one last dance before breaking up

Serena wasn’t the perfect decision-maker on Gossip Girl, from trusting the incorrect individuals, or getting too concerned in different individuals’s affairs, she made many poor judgment calls. Yet, indubitably, the worst resolution she made was when she seduced Dan into sleeping together with her, so she may movie it and get again at Blair for beginning a relationship with him within the first place.

“The Return of the King,” confirmed Serena at her worst, as she tried to make up for leaking Blair’s diary to Gossip Girl, solely to return on herself and proceed to make unhealthy selections. Serena manipulated Dan by making him imagine that Blair was leaving him for Chuck, tricked him into sleeping together with her after which filmed it with out his consent. In a present crammed with over-the-top revenge plots, this was too far and was undoubtedly essentially the most warped resolution she ever have made.

2 Blair: Exposing Serena’s Secrets

Serena Blair Gossip Girl featured

It’s no shock for followers of Gossip Girl that Serena and Blair’s friendship could be very toxic at instances, and Blair’s remedy of Serena in season 2 was proof of this. In “New Haven Can Wait,” Blair was understandably upset that Serena had utilized to Yale, understanding it had been Blair’s dream faculty she was a baby, and she or he solely received extra offended when Serena stole one in every of her concepts because the Dean’s reception celebration.

Rather than act like the larger individual, Blair determined to as a substitute expose Serena’s tragic previous to everybody on the celebration, together with the Dean, in a very malicious means. Serena had witnessed a person die of a drug overdose earlier than she initially left New York, and Blair knew how a lot guilt she harbored over the scenario and had even helped her by means of it. Yet, Blair used it in opposition to Serena, and the choice to take action together with the motives behind it, have been terrible.

1 Dan: Running Gossip Girl

There are so many issues that Dan did when hidden beneath his id as Gossip Girl, that to single out only one unhealthy resolution he made is troublesome. Therefore, the creation and continuation of the notorious gossip website itself, and all of the drama it induced, needs to be the worst resolution Dan ever made.

Whilst the entire premise of the present rests on Gossip Girl, that does not imply it was a good suggestion within the first place. Hidden beneath the pseudonym, Dan made many poor judgment calls that had catastrophic penalties, and betrayed his buddies’ privateness a number of instances. Most notably, in “Riding in Town Cars With Boys,” his resolution to put up a tip he obtained inadvertently induced Blair and Chuck’s automobile to crash and resulted in Blair having a miscarriage.

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