If there was ever a show that thrived on scandal and impropriety, it's Gossip Girl. The Upper East Side gang were young, carefree, and rich — a sure-shot formula for doing outrageous things with impunity. Not only did Blair, Serena, Chuck, Nate, Dan and the others involve themselves in some truly shocking things, but also the parents had their own secrets and agendas going on in the background.
From forbidden romances with the faculty to trading each other for hotels, the Gossip Girl characters left no scandalous stone unturned while navigating their lives, and of course, all of it was documented by Dan for posterity. It's pretty hard to imagine how their kids would react when they read about all the crazy things their parents did as teens and young adults.
Serena's Teacher Romances
If there was one pattern the golden girl of the UES liked to repeat, it was romancing her teachers. Of Serena's boyfriends on Gossip Girl, two were professors. When she ran away to boarding school, she met Ben Donovan, with whom she became emotionally involved (which led to his arrest), and then later had an affair with Colin, a visiting professor at Columbia.
The power dynamic between a teacher-student relationship is always skewed, and that these privileged young ones thought it was okay to do was quite astounding. Most importantly, it reflects poorly on the grown men who were in charge of educating teens but chose to date them instead.
Chuck Trading Blair For A Hotel
The gang was notoriously cliquish, but they didn't hesitate to sell each other out for their businesses and power. One of the most unexpected events on GG was when Chuck decided to trade in Blair, the love of his life, to Jack Bass to get his hotel back.
At first glance, it was incredibly irresponsible of Chuck to lose a hotel, but as a billionaire, he would have definitely had other assets to lean on if the Empire went away. He broke hearts, and probably a few laws in his sordid deal with Jack. It was perhaps the most scandalous thing to happen on the show.
The Whole Ivy Saga
Season 4 saw the introduction of Charlie Rhodes to the circle, or rather Ivy Dickens impersonating the Rhodes cousin on the behest of Carol. The entire storyline was wicked from the beginning to end, with Carol hiring Ivy to get control over her own daughter's estate, several occasions of blackmail, and the final revelation of her identity.
What made this even more shocking was that the Rhodes grandma left Ivy her whole estate, knowing full well that she was essentially a con woman. None of it made sense, but it was a saga that played out in their media for a while and wouldn't be forgotten.
Rufus And Lily's Child
The 80s rockstar and the socialite extraordinaire who were Dan and Serena's father and mother had an intense love affair in their youth, which resulted in a baby that even Rufus himself had not known about. Apart from the fact that a child had been secretly given up for adoption, this event became even more interesting when Lily became Bart Bass' wife and had a rekindling with Rufus at the same time.
It kept getting even more outrageous because this meant that Serena and Dan, who were together at the time, shared a half-sibling which made their relationship even more incestuous than it already was.
Dan And Ms. Carr
Dan was a contentious character, but he acted like the dreaded "nice guy" when he shamed Serena for getting with teachers after he did the same thing himself. He shared a hugely inappropriate relationship with Ms. Carr, got intimate with her, and then had sex with her as she believed that she had been fired.
Things became far more complicated when she realized that she was not terminated, and had to continue working at Constance, knowing what she had done. The school's reaction to the incident was shameful, and so was the way Dan and Ms. Carr behaved with each other.
Blair's Doomed Royal Wedding
Prince Louis was one of the most deceptive villains of Gossip Girl, and he made sure that Blair paid for embarrassing him in front of others one too many times. Their courtship had been fraught with tension throughout, with Blair's pregnancy, Chuck's presence, and her immature behavior, but she didn't deserve to be caught in a contract.
A royal wedding is a big deal, but Louis used it as a way of getting back at Blair for her mistakes, which is a scandal of a global scale. The wedding was a sham, the couple never spent time together, and big sums of money were covertly paid to Monaco to end it.
Dan Publishing Inside
While it had been Dan's dream to be a published author, almost everything he wrote was borrowed from the real-life events of his peers on the Upper East Side. He never took their permission or even gave them a heads up that his book Inside was about their lives, with slightly altered names.
Considering how tight these circles run, it was definitely defamation that he released the book about their lives and reaped profit form it, and it was a miracle that they didn't sue him for it.
Catherine, Nate, And Marcus' Love Triangle
Early in the show, the scandals and OMG moments came strong, and Nate's affinity to older women was revealed to viewers. He got together with Catherine in the Hamptons, and they had an interesting relationship that continued in Manhattan as blackmail, but things got even more complicated when she was revealed to be Marcus' stepmother.
Nate was then unwittingly caught in a seriously sordid romance between stepmother and son, as Catherine and Marcus were revealed to be sleeping together secretly, while she was using Nate and paying him to bail his family out. Yikes.
Blair And Serena's Yale Catfight
The two best friends fought very often so this may seem like an everyday affair, but the fact that they made a show of themselves in front of Yale faculty made it quite outrageous. Serena vowed to steal Yale from Blair, and Blair revealed that Serena was involved in a death by overdose publicly.
The physical fight that ensued was a complete shock, and even more so when it's revealed that it had no effect on Blair's Yale admission later. Surely a scene like that would incite disciplinary action and prevent her admission.
Bart Dying, Then Returning, Then Dying Again
Bart Bass was an enigma of sorts, with his massive wealth and stoic nature. His death was a complete shock that hurt Chuck the most, so when he was shown to be alive many years later, fans were amazed. For a billionaire of his stature to be able to fake his death and stay under the radar was next to impossible, but he did it anyway.
Unfortunately, his return did not signal good times. He seized all of Chuck's assets and his hard work, and the enmity led to a very unseemly death at the hands of Chuck, which was covered up hurriedly by everyone. The world of GG was never to know what happened that night.