Gossip Girl: The Worst Thing Every Main Character Did, Ranked

Gossip Girl is a very popular teen drama series that was on from 2007 to 2012. It focused on a group of friends who lived on the Upper East Side of Manhattan and whose every moves were shared with the world via an anonymous blogger.

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Due to these characters backgrounds, setting, resources, personalities and lives, they did not always make the best decisions, nor did they always treat others how they wanted to be treated. Sure, it all made for some super exciting scenes, but let’s really think back to all the horrible things these main characters did on this show.

10 Nate Archibald: Cheating On Blair

Nate Archibald was the golden boy of the group, and that title meant even more, when comparing the bad things he did to the bad things his peers did. He never even sent in a tip to Gossip Girl, ever! He did have a way with the ladies, though, and that sometimes got him in trouble.

He had an affair with a married woman. He was in a toxic relationship with his boss. And he cheated on his girlfriend with her best friend. That was not the best decision, but it can’t begin to compare to what others on the show did…

9 Rufus Humphrey: Sleeping With Ivy

Rufus was another one of the good guys on the show; he lived in Brooklyn, he worked to provide for his family, and he always tried to do the right thing. There was that time he was with Ivy, though.

Ivy pretended to be related to the van der Woodsens, and she tried to take their home, tried to take their money and tried to take them down. After all of that, Rufus got conned by this supporting character, too, and they were even involved for a little bit. Yes, he was in love with Lily van der Woodsen, but he slept with Ivy!

8 Jenny Humphrey: Losing Herself

On the Upper East Side, people were constantly fighting to be in the spotlight, and as evident by this article, all the main characters took things too far, in order to have power, fame and popularity. Jenny Humphrey really lost herself along the way and ended up treating her loved ones super poorly.

She used to just be Little J, but after she got a taste of the queen bee life, that is all she wanted. She changed her looks. She had a new bad attitude. She didn’t care that she was being mean to her friends and family members. All she wanted was that top position on the Met steps. This was especially sad to see since a. Rufus raised his kids to be better and b. Jenny realized it wasn’t really worth it in the end.

7 Vanessa Abrams: Helping To Drug Serena

In Season 4, Vanessa and Jenny teamed up with Juliet, in order to take Serena down. Yes, Jenny was involved in this not-so-great moment, too, but she came clean, while Juliet convinced Vanessa that the Humphrey family would never forgive her, if she were to confess.

Even though Vanessa was clearly threatened by Serena over the years, this was another plan that was taken much too far. Juliet is the main person to blame, but if Vanessa really loved Dan, then she would never have agreed to be part of a scheme that drugged Serena, got her dropped out of Columbia and put her in the Ostroff Center.

6 Georgina Sparks: Lying About Milo

When Georgina Sparks showed up in this series, things got even more dramatic. And one time, her entrance included a baby… which she said was Dan’s.

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Of course, this turned out to be a lie, but that was not revealed until it was too late; Dan got attached to baby Milo, and Georgina even left them alone, while she was off on a vacation. Dan may have spread gossip about his loved ones, but he stepped up and did the right thing quite often, including when Georgina told him this very big lie.

5 Lily van der Woodsen: Sending An Innocent Man To Prison

Lily van der Woodsen had money, power and status, meaning she could make things happen. Some of her questionable decisions were made to protect her family, yet she still ended up sending an innocent man to prison.

When Lily went to Serena’s old school, she heard some gossip about Serena and Ben, Serena’s favorite teacher. She then told the school that she was afraid a teacher was being inappropriate with her daughter. She signed an affidavit as Serena, which landed Ben in prison.

4 Chuck Bass: His Unwanted Advances

Chuck Bass could do whatever he pleased, and that usually involved women and alcohol. Over the years, he did a lot of growing up, resulting in him and Blair finally being able to be together. Before that, though, there were some real mistakes made.

He threw himself on Serena, he forced himself onto Jenny, and he came off as super creepy and sleazy at the beginning of this show, as he seemed to act without thinking of those who were involved and without thinking period.

3 Dan Humphrey: He Spread Gossip

Dan Humphrey went to the same school as his peers within this story, and he even ended up dating the most popular girl at school and befriending some of her friends. Still, he always felt like he was on the outside. Therefore, the biggest spoiler alert ever is that he started the Gossip Girl blog.

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Expressing oneself through writing can be very beneficial, but bashing one’s friends and family members is not cool. The list would go on and on, when naming all the not-so-nice things Dan wrote about his loved ones on this blog and in his book.

2 Serena van der Woodsen: Pete Lost His Life

From being called self-centered (over and over) to purposefully trying to hurt her so-called BFF (several times), there were several not-so-great moments from the show’s it girl, Serena van der Woodsen. However, there was one pretty big instance that needs to be mentioned...

During one of Serena’s and Georgina’s crazy nights together, they ended up with a guy named Pete. Georgina and Pete were planning on videoing Serena (in an adult and inappropriate way), and drugs were involved. Pete took too much and overdosed, leading to Serena’s eventual confession of taking a man’s life. While this was not necessarily 100% her fault, there were so many other ways the situation could have been handled.

1 Blair Waldorf: Bringing Up Pete

Blair Waldorf was the queen B, but she worked hard to get and stay in that position… by bossing people around, acting out in selfish ways, spreading rumors about people and even trying to sabotage her bestie.

As mentioned, both Blair and Serena did horrid things to one another, but one moment, specifically, was taken way too far: Both characters visit Yale University and get invited to an event at the dean’s house. There, Dean Baraby asks everyone who they would most like to have dinner with, and on Serena’s card, Blair writes “Pete Fairman”. While Serena stands there, stunned, Blair blurts out that this is the man Serena killed. While both these friends were trying to one-up the other during this part of the show, Blair crossed a line with this move.

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