20 Times Gossip Girl Went Too Far
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Gossip Girl had more than its fair share of crazy, over-the-top moments over its six seasons, especially for a teen drama.
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The Gossip Girl TV show may never have gotten as scandalous as the books did, and it would never have aired on the CW if it did. The show still had its fair share of insane moments – and in some cases, those big, shocking moments took things a bit too far, especially considering that the series was about teenagers.
Their parents were involved, too, and most of the surprising storylines didn’t involve them, or at least not just them. Although there was at least one moment that involved one of the parents and a fake kid.
Some moments involved the ending of lives, some involved people getting payback in very extreme ways that could have left others open to being taken advantage of, and others involved lying. Most of these things were all too common on Gossip Girl, but in these instances, they never should have happened. Especially when they didn’t seem to have any impact on the characters later on.
The series finale had plenty of outrageous moments, a few even stemming from the big reveal that Dan was Gossip Girl. Some reactions just didn’t fit the reveal, yet the series wanted its fans to believe that the reactions were warranted.
Here are 20 Times Gossip Girl Went Too Far.
20 Jenny’s Guerilla Fashion Show
In season 2’s “There Might Be Blood”, Jenny and Agnes planned a guerilla fashion show to show off their line and get financial backers. Where better to do that than at the New York Philanthropic Society’s Annual Gala? They needed people with money who could get them press.
The idea behind the fashion show was a sound concept, but that was about it. It was absolutely ridiculous that Agnes just happened to know the computer guy, and he just happened to be in love with her. He was also about to quit his job, so he didn’t care much and let them take over the system.
Just as an award was being presented to Lily and Bart, Jenny’s fashion show began, and the models danced on tables while throwing around her business cards.
They even kicked some glasses and broke them while doing so, and yet, no one was really angry, even as they were escorted out.
Yes, Jenny apologized, but Lily said it was amazing and didn’t see any problem with what she had done. Rufus was the only one who was seemingly bothered, and he even turned his daughter over to an officer as the one responsible.
The reactions on both sides were a bit extreme; Lily should have cared about the interruption, but Rufus shouldn’t have turned on Jenny like that.
19 Dan Saw Rufus and Ivy Together
In the season 6 premiere, “Gone Maybe Gone”, it was revealed that Ivy had moved into the Humphreys’ loft over the summer. Understandably, Lily wasn’t pleased when she found out, but Ivy used that to her advantage as she manipulated Rufus – and it wasn’t like he made it hard for her to do so.
Ivy kept telling Rufus he was a good person throughout the episode and basically worked on turning him against Lily. She didn’t appreciate him, Ivy claimed, and he needed to get away from her. He was a good person, she reiterated, and he cared about other people. She even suggested that Lily was threatened by Ivy and didn’t deserve Rufus.
All it really took was Ivy telling Rufus, “I’m not a kid, you’re not married,” for him to give in and kiss her back. He really should have shown more restraint, given their age difference. Having to remind someone that you’re not a kid is not something that should be said before a kiss. That would have been bad enough.
However, then Dan arrived home and walked into the loft to find Rufus and Ivy together. That was an image that no one should have ever had to see.
18 Blair’s Sabotage
In season 2’s “New Haven Can Wait”, Blair and Serena’s fight got very, very public – and in the wrong setting. When Blair told Serena that she wouldn’t make it past the first round of admissions at Yale, no matter how hard she tried, Serena decided to prove her wrong.
Not only did Serena win over the dean and score an invite to his private reception, but she also decided to steal Blair’s answer to the question he’d ask there.
Blair didn’t put her best foot forward with the dean, but she did manage to get her own invitation to the event.
Upon learning what Serena planned to do, Blair changed her answer to Pete’s name, and, not only did Serena have to recount what had happened – though she did acknowledge she wasn’t responsible, like she had thought upon her return from boarding school – but Blair also brought up other wild aspects of her past.
Serena pulled her away, but they’d already made a bit of a scene in the middle of the reception. Outside, it continued, with Blair throwing her bag at Serena, and so began a catfight, complete with pulling each other’s hair, right outside the event.
17 Juliet Pretended to Be Serena
In season 4’s “The Witches of Bushwick”, Juliet donned the same dress and mask as Serena at a masquerade party and pretended to be her. She kissed both Nate and Dan.
After putting something on her mask, Juliet switched it with Serena’s, and she was the one who found Serena stumbling outside on the street. She pretended to be helping her and got her into a cab, but while Serena was passed out, Juliet used her phone to withdraw her from college.
That would have been bad enough and taking things too far, but Juliet then left Serena in a motel. She then staged the scene to make it look like she had knowingly taken medication that was on the nightstand.
In the next episode, “Gaslit”, Serena’s family had her checked into the Ostroff Treatment Center. It looked like the story being told was true, especially when Juliet sent a photo of herself partaking in some partying while dressed as Serena to Gossip Girl.
Pretending to be Serena and messing with her friends’ lives was one thing, but Juliet took it too far as soon as she switched their masks and then perpetuated the story everyone believed to be true with the staged photo.
16 Scott’s Adoptive Parents Lied About Their Son
Lily and Rufus had a son, but when they met with his adoptive father in season 2’s “Gone with the Will”, they were informed that Andrew had passed. He had been sailing with friends the previous year, when he jumped in the water and was caught in the riptide. The parents struggled with the news.
It was too painful to tell them or anyone, Chris Rosson claimed, and he even showed them the newspaper clipping about the accident.
It was sad and tragic, but no one was at fault, or so it seemed.
It turned out that Chris had lied to Lily and Rufus. His wife felt awful, but he justified it by explaining that they had money and lawyers — not to mention they’d already lost one son. They couldn’t lose another.
This means that the son they lost wasn’t the one they adopted, and they didn’t want to lose the only child they had left. What was worse was that this decision seemed to have been made based on things they assumed about Lily and Rufus — that they would lose Scott to them.
This storyline didn’t exactly have the best resolution either, with Scott even pretending to be their son’s brother for a while before the truth ultimately came out, but then after the happy reunion, it was never mentioned again.
15 William Lied to Lily About Her Health
In season 3’s “Dr. Estrangeloved”, it was revealed that the reason Lily and William spend time together over the summer wasn’t because Lily’s mother was sick, but because she was. William even used that as an excuse as to why he couldn’t see Serena; he didn’t want to lie to her, but couldn’t say anything as Lily’s doctor.
Lily had just had her six-month checkup and was feeling good. William said he was feeling optimistic, but they were still waiting for results.
Skip forward a couple episodes, to “Ex-Husbands and Wives”, and the truth came out. Lily had been sick, yes, but William fell in love with her again and thought the only way to get his family back after he messed things up was to put her in a position where he cured her again. He gave her medication that mimicked symptoms she’d have.
Somehow, everyone didn’t hate him after that. Trying to get back in his ex’s good graces and find a way to make his family not hate him would be one thing, but making Lily believe that she was sick again was another. Since Gossip Girl wanted to do that storyline, it would have been better to, at least, have everyone react like normal people would.
14 As If Mayor Bloomberg Would Care About Gossip Girl
In the series finale, the truth finally came out about who was behind Gossip Girl, and it was none other than Dan. It was the big question of the entire six seasons of the show, and as soon as it was time to reveal it, “New York, I Love You XOXO” showed various reactions to the news blast.
Somehow, Gossip Girl expected viewers to truly believe that the identity of a gossip blogger mattered to Mayor Bloomberg.
The mayor’s reaction was even shown on the show. “I’m shocked,” he said. “I thought it was Dorota.”
Come to think of it, maybe he too was going through the list of reasons it couldn’t be Dan. If fans were required to truly think that he cared, he might as well have had a reason behind his guess.
The rest of the reactions shown beyond the main group at least made sense. Lola, Vanessa, Juliet, and Agnes’ responses to reading who it was were shown next. It all ended with a wink to the audience, as Kristen Bell, the voice of Gossip Girl, helped Rachel Bilson with a reading as Serena and Blair (though she didn’t think she could pull off high school anymore).
“OMG, you are not going to believe who Gossip Girl is,” Bell said.
13 Serena’s Reaction to Dan Being Gossip Girl
After everything Gossip Girl did and revealed about Serena, she, more than anyone, had a reason to be mad. She even said so herself in the series finale. That would have been anyone’s very normal, very understandable reaction.
In fact, the other person who had the right to be just as mad, was Blair, and that was her response. “Gossip Girl ruined our lives,” Blair protested, unable to understand how the others thought it was funny. They instead chose to focus on how they didn’t see it before, or reminisce on their guesses for the blogger’s identity.
Serena admitted she felt the same way until she realized she was fine with it. In her eyes, Dan was just as hard on himself as any of them were. They all played a role since he wouldn’t have had anything to post if everyone hadn’t sent in tips. With that, it seemed like she absolved him of all blame for the trouble he’d caused.
It just got worse, as Serena then said that, with the power he had by being the one pulling the strings, he wrote “a love letter” to her and the others. She really did feel that way, as she ended up marrying him after the five-year time jump.
12 Georgina manipulates Serena
In season 1’s “Desperately Seeking Serena”, everyone was busy studying for the SATs and Georgina was stirring up trouble. First, she invited Serena to catch up over a drink, but Serena left when she didn’t want to party like she used to. The next day, Georgina then claimed that she saw Serena had changed and wanted to catch up again, this time just over dinner.
Serena, for some unknown reason, accepted, even though it was the night before the SATs.
Despite how nice Georgina seemingly was, Serena still woke up the next morning, unable to remember how she got to her friend’s.
Georgina claimed that Serena switched from soda (she did not) and she even took care of her, calling her mother to cover and keeping her away from “one of [her] many suitors.”
Because of Georgina’s actions, Serena missed the test, but Chuck paid someone to take it for her. “You went too far,” Serena told her, and no one deserved to hear those words more than Georgina. She had so very clearly wanted to bring the person she knew, the old Serena, back so much that she took advantage of her and played nice when she had the complete opposite in mind.
11 Teens help the NYPD catch Chuck
Gossip Girl expected fans to accept a lot in the series finale, with the big reveal being the most outrageous moment. The show also relied a lot on coincidence to sell one of the plot points: the police finding Chuck.
Thea and Allie just so happened to be on the steps of the Metropolitan Museum of Art at the right time to see Serena, Dan, Nate, and Georgina head inside. They followed them and happened to overhear them discussing Blair and Chuck’s wedding. They sent the tip into Gossip Girl, which made sense.
When Gossip Girl didn’t post the tip, given who was behind the site, they decided to call the police instead. Chuck was a fugitive, and it would at least be on the news, Thea figured. Nate just so happened to be there to overhear (and warn the others) and the two teens who spotted him heading into the MET earlier completely missed him.
The police actually followed up on the tip and found Chuck just as he and Blair got married. It was one thing to have Gossip Girl post tips from teenagers. It was another to have the NYPD do so (though they were right).
10 Chuck Trades Blair For A Building
In season 3’s “Inglorious Bassterds”, Chuck and Jack fought over ownership of The Empire. Chuck was willing to do anything to get his hotel back – except give in to Jack’s demand that Blair romance him – or so he said.
Blair took matters into her own hands after Jack approached her (though she refused at first) and manipulated her into agreeing to fix it for Chuck, who didn’t want to see his hotel fail.
Jack only kissed Blair before revealing that he wasn’t going to go any further, and that Chuck had to make a choice between his hotel and Blair.
Chuck chose to give Jack his girlfriend. He knew which buttons he needed to push, Jack said.
As Blair then learned, that was the truth. Chuck admitted to her that he couldn’t have just asked for her help because Jack would’ve known when he approached her. He did what he had to do to win. He even had the gall to tell Blair, “You went up there on your own.”
Yes, Chuck basically traded Blair for a hotel, and that was just awful. The only good part of that was that by doing so, he lost her at that time.
9 Jenny Used Gossip Girl’s Identity For Herself
Rufus was one of the few who had a human reaction to the reveal that Dan was Gossip Girl. He even pointed out the damage he did to his friends and family, including his own sister. After all, Gossip Girl posted some horrible things about everyone, including Jenny.
However, that was when Dan told his father that Jenny knew it was him for years and wanted to get on the gossip site — she only had to ask if she didn’t want something posted. This inevitably means she was okay with everything that was posted about her.
That included the world finding out about her losing her innocence. She sent the tip in herself, Dan said. She wanted to get out of New York and didn’t have the strength to leave on her own. She, therefore, used Gossip Girl to make sure Blair would find out the truth. That was an extreme move to do just to get out of a situation she didn’t want to be in.
Rufus then agreed that leaving town was the best thing to happen to Jenny, and that problem was resolved just as quickly as every other one attached to the big reveal of Gossip Girl’ identity.
8 Blair went back to Chuck after Dan
Gossip Girl had to draw out Chuck and Blair eventually getting back together, and that meant they would be having other relationships. Blair even married a prince, and then dated Dan Humphrey after a very long build up of friendship.
The problem wasn’t that they kissed. They could have just done that, even more than once, but then they had Blair tell Dan that she told Chuck he didn’t have her heart anymore in season 5’s “The Princess Dowry”. Then Dan and Blair were in a supportive, healthy relationship
Then, the season 5 finale, “The Return of the Ring,” saw Blair tell Chuck she was in love with him and didn’t want to be with Dan anymore.
Instead, in the beginning of season 6, Dan moved in with Blair and tried to win her back while she ignored and suffered neglect from Chuck. Like other storylines, it was drawn out for too many episodes, and it should never have even been a plot point in the final season. The reason for this is that only a handful of episodes later, Blair and Chuck would get married, and Dan and Serena would as well after a time jump.
7 Georgina’s Baby Daddy
This entire storyline went too far — from the moment Georgina showed up at Dan’s door in the season 3 finale, she was very pregnant, and her way of telling him he was the father was, “I have something of yours.” Those words came out of her mouth in lieu of “it’s yours” or “you’re going to be a father.”
Of course, Dan wasn’t actually the baby’s father, but he didn’t find out the truth until after Georgina had given birth — he had already started taking care of her, and his, as he thought at the time, son. Three episodes into season 4, in “The Undergraduates”, the truth came out.
According to Georgina, she had gotten together with a Russian businessman, and when he told his wife that she was having his baby, his wife threatened to have her life ended. Georgina then escaped to Brooklyn and decided her best bet was to make Serge’s wife believe the baby wasn’t his. She thought Dan was the only guy decent enough to take on the responsibility.
Georgina then ended up just leaving with her baby, and that was that. Sorry, Dan, you are not the father, but you were the caretaker for a while.
6 Don’t Mess With Agnes
Just like Georgina played nice with Serena before turning on her, Agnes did the same thing to Jenny. The two teenagers both apologized and seemed to be back on track, despite their failed fashion line. Agnes even offered to help her get payback against her no-good ex-boyfriend.
Agnes had ulterior motives — she took illegal substances Jenny had in her bag, and handed the item out to other models before a fashion show.
Even if Jenny tried to tell Eleanor, as she didn’t want to risk the show being ruined, she didn’t stand a chance.
It just got worse when Agnes had a friend give Jenny a congratulatory toast supposedly from Eleanor (only it wasn’t), and it was revealed that she had also put the substance in Jenny’s drink. This was Agnes getting her payback.
Agnes even left her in her vulnerable state with some guys, who left her nearly passed out on a couch. Fortunately, Jenny managed to call Nate for help and he retrieved her before anything could happen to her.
While Jenny should never have trusted Agnes – who even took her phone and called her ex to set up a meet when Jenny didn’t want to deal with him again – the teen model took things too far.
5 Jenny And Chuck Got A Little Too Close
In the pilot, Jenny and Chuck spent time together at a party, and at first, everything was fine, even with his obvious “let’s go somewhere quieter” before he brought her up to the roof. He even apologized and said they’d start over when he seemed to be moving faster than she was comfortable with. Then he offered her champagne.
By the time Dan arrived after receiving a text message requesting help (and including the word “emergency”) from Jenny, Chuck was pushing the issue again and trying to coerce her. Furthermore, he didn’t even see anything wrong with it because “it’s a party, things happen.”
A few years later, in the season 3 finale, “Last Tango, Then Paris”, Jenny lost her innocence to Chuck. This time, he did give her an out if she wanted to leave when they were in his bedroom, but she didn’t take it, and told him she didn’t want to be alone.
Jenny did end up using what happened to her advantage, which also ended up being the right move for her in the long run, but it’s still wrong that Gossip Girl had her lose her innocence to Chuck after what he attempted in the pilot.
4 Why Serena Ran Off to Boarding School
It took until episodes 16, “All About My Brother”, and 17, “Woman on the Verge”, of the first season for the truth about why Serena ran off to boarding school to come out: she felt responsible for the passing of someone she knew due to substance abuse.
It then became just one of several storylines that was simply forgotten, like Rufus and Lily’s love child who was never seen again.
First, it was teased at the end of episode 16, with Serena telling Blair that she was the reason someone passed away.
The teaser was for dramatic effect, because the next episode saw the entire truth revealed about what happened the night Serena decided to run off to boarding school.
Georgina had planned on getting Serena on tape with a guy, Pete, but Serena had felt too guilty about being with Nate to be much fun. Instead, Serena had suggested that they party first, but he had a bad reaction. Georgina didn’t want to call the police because they could get in trouble for the paraphernalia in the room, but Serena still dialed 911 on her way out.
Rather than leave with Georgina, she watched from across the street and saw that the paramedics couldn’t help Pete — he had passed away, which is why Serena blamed herself.
3 One Step Too Many?
At times, it was difficult to tell whether Bart was alive, or whether it was time to attend his funeral, and sometimes, it became questionable whether he was really alive. Bart’s status among the living (and his feelings about his son’s life) was a wildcard.
It wasn’t until the penultimate episode of the series that that matter was resolved. After announcing that his father didn’t care about honoring life, because of an attempt to have his own son’s life ended, Chuck was escorted to the roof.
Chuck tried to record his father’s confession on his phone, but Bart knew what he was doing and put a stop to that, warning him that accidents could happen at any time. What followed was a back-and-forth about what made a man (taking responsibility, taking care of family, not threatening his own son’s life) and Bart insisting, that with the police commissioner in his pocket, no one would believe Chuck.
The physical fighting between father and son was weak at best, but all it really took was Chuck stepping to the side when Bart advanced on him for Bart to go over the side of the roof. He was holding onto the railing when he insisted he would never truly hurt his son, but Chuck and Blair just stood there and watched him let go and fall.
2 Using A Therapist For The Opposite Of What’s Intended
Chuck went to therapy in season 5, after meeting Dr. Barnes at the park in “The Fasting and the Furious”. He tried to hit on her, but she wasn’t having it, and instead, insisted she’d only be available to him professionally. Given the number of inappropriate relationships on the show, that was refreshing.
The next episode saw Chuck going to her as a patient. She knew there was something he was holding back from her (Blair), though he denied it.
It turned out that Blair was why she was there, at least partly.
Louis was paying her to make sure Blair wouldn’t fall for Chuck again, to turn him back into the monster he was for 20 years.
He wanted her to enrage him deliberately, and she tried to do just that. Surprisingly, Chuck didn’t bite, and instead gave her the ring he’d gotten for Blair to get rid of as a sign that he truly was letting her go.
When Chuck saw her meeting with Louis to sever their deal, he assumed Dr. Barnes was being paid to reveal confidential information about him and he publicly confronted her. Louis managed to come out on top with Blair, and told her he needed her to see Chuck was always the wrong choice.
As for Dr. Barnes, she told Chuck why Louis paid her and told him that he could change, pointing out his reaction when she tried to provoke him about Blair.
1 A College Experience
When actress Olivia Burke was going to leave to film a movie in season 3’s “They Shoot Humphreys, Don’t They”, Dan and Vanessa decided to give her a real college experience by following a list, “The 15 Things Every College Student Must Do Before Graduating,” to convince her to stay.
There were some crazier items on the list, which had nothing to do with academics , which meant she couldn’t complete them from the location like she could schoolwork. It also included cheering themselves hoarse at a sporting event, attending a college party, and dancing in a fountain.
Olivia decided that she was going to take the part, explaining that too many people were depending on her for the movie. She had grown up on the sets of the series and the crew was like her family.
Once the actress found out about the list they used to try to change her mind, she insisted that they finish it, even though they’d already gotten through 14 of the 15 items — the last one was some pretty wild experimentation.
Olivia was only around for one episode after that one, so it didn’t seem like there was much of a reason other than the shock factor for Gossip Girl to include that.
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