The place of Gossip Girl lore is the home to many things: galas, private clubs, high-end restaurants, and expensive boutiques. The characters we know and love (and sometimes hate) may cut big checks to charity, and each other - such as when Chuck paid off Blair's dowry to the Grimaldis to get her out of her marriage - but this bunch could be as backstabbing as it was philanthropic.
There was the time Serena fell for Nate's politician cousin Tripp and believed he was going to leave his wife, only to find out she was going to be the Marilyn Monroe of the trio. And how can we forget when Dr. William van der Woodsen faked Lily's cancer diagnosis in order to then play savior to win her back? And that was just the tip of the iceberg.
When Serena Slept With Nate
Before Serena left NYC, she and Nate - who was Blair's boyfriend - had sex. Upon Serena's return, Blair tries to keep them apart fearing Nate still has feelings for her bohemian frenemy, even planning ways to get Nate in bed so he'd be more interested in her than the glamorous blonde.
This backfires in many ways at the Kiss on the Lips party, when Blair sends Nate on a treasure hunt with the prize being herself, but Nate seeks out Serena, declares his love, only to have it be Jenny Humphrey in the same costume. Being cheated on hurts, but when it's your BFF that your boyfriend likes better than you, that's a heartbreak double whammy.
When Fathers Betrayed Sons
Nate's dad Howard, who was pushing his son to stay on the straight and narrow path to Dartmouth, gets arrested for drug possession, fraud and embezzlement, mom Anne bails him out only to have Howard skip town. Now penniless, Nate lives alone in a furniture-less townhouse and sleeps with the wealthy Catherine for money.
Chuck's father Bart faked his own death, leaving his son to believe he was now an orphan. Finding out that the people whose job it is to take care of you are only interested in themselves not only makes one feel betrayed, but abandoned.
When Jenny Betrayed Eric
Jenny the BK outsider befriended Serena's little brother who was also ostracized by the UES gang due to his suicide attempt. At the same time, she is trying desperately to become one of Blair's minions and hang on the steps of The Met, where no one is allowed to sit higher than the headbanded one.
By season 3, Jenny has officially begun her reign as the new queen of Constance Billard School, even modeling Blair's museum hierarchy behavior commanding Eric to move down a few steps. Eric is offended that his Little J chose status over their friendship and disappointed that she lost her down-to-earth quality.
When Chuck Betrayed Jenny
Little J volunteers to handwrite the invitations for Blair's Kiss on the Lips party in exchange to be able to attend. She is extremely flattered when Chuck flirts with her and invites her to the roof to hang out.
Naive Jenny goes with him thinking he just wants a quiet place to get to know her, but then he attempts to force himself on her. Luckily, the assault was stopped by Serena and Dan. It's easy when you're young and inexperienced to trust someone who is being nice to you, and feel betrayed, as well as mistakenly and wrongly blame yourself, for not realizing the person's true motives.
When Blair & Louis Betrayed Each Other
The Penthouse Princess met a real prince and the fairy tale vision Blair always had for her adult life was coming true. Blair marries Louis but at the wedding confesses to Chuck that she still loves him, which is recorded by Georgina who sends it to Gossip Girl. Louis tells Blair their marriage is now just for appearances, in private they will live separate lives.
Blair plays the runaway bride but returns realizing the terms of the prenup will bankrupt her family. Louis had every right to feel betrayed that his fiancé was in love with another, but he should not have gone through with the ceremony knowing what he knew.
When Sage Betrayed Blair
17 and savvy, Sage - who is dating Nate who's now a newspaper editor - hates that Serena is in a relationship that could lead to marriage with her dad Steven. When Blair, now in charge of Waldorf Designs, wants Sage to wear a new hip dress to cotillon, the teen agrees on the condition that Blair help her break up Steven and Serena.
When Blair doesn't come through, Sage takes matters into her own hands, sabotaging the dress as well. It's hard on children when a parent moves on to a new partner, making it clear that their mom and dad will never get back together.
When Juliet Betrayed Serena & Nate
She accidentally on purpose ran into Nate and began dating him, giving him the impression that she was part of his high society circle, by scamming the keys to a massive Riverside Drive apartment and claiming it was hers.
Juliet used him to get to Serena in order to enact revenge because Lily falsely accused Juliet's teacher brother of sexually harassing Serena at boarding school and had him thrown in prison. There is no doubt that Juliet should have tried her best to get her innocent brother out from behind bars, but she seemed to waste her energies manipulated Nate and Serena, when she and her brother would have been better served by a good lawyer.
When Ivy & Carol Betrayed Lily & Family
Lily's sister Carol wanted her daughter Charlie to get her share of family money, but because there was such bad blood between the siblings as well as Carol and her mother CeCe, the estranged sister hired an out of work actress named Ivy to go to NYC and pose as Charlie.
But once Ivy/Charlie got in with the in-crowd and started to enjoy how the other half lived, the betrayal took on a new direction. Tolstoy wrote: "Every unhappy family is unhappy in its own way," and the Rhodes were no exception. But hiring someone to pretend she's your daughter, took betrayal to a new low - if that's possible.
When Georgina Betrayed Dan
The ever-exhausting former sidekick of Serena never met a pot she didn't want to stir to get the Upper East Siders in trouble, to break up, or worse - such as getting pregnant by a married Russian guy and then to avoid having his wife put a hit out on her and the baby, pretending Milo is really Dan's son.
Luckily, Rufus figured that given the kid's blood type, he couldn't possibly be Dan's. Georgina, who took off, returns and comes clean about what happened then takes the baby and goes to live with her parents. Yes, a mother should do anything to protect her child, but turning people's worlds upside down like this? Just no.
When Dan Betrayed Everyone
And then everyone found out that Dan was Gossip Girl. Whether it actually made sense, which a lot of the time it didn't, matters not. What's done is done. Pile on the fact that Dan also wrote a tell-all about his friends, it's surprising he had any left.
There is a an unspoken rule among friends that what they share with you goes into the proverbial vault, not to be blabbed around town to anyone within earshot. Unassuming Dan from Brooklyn broke this promise of trust so many times in two different mediums that all that can be said is those Upper East Siders are a forgiving bunch.