BLAIR LOST HER VIRGINITY TO CHUCK — IN THE BACK OF HIS LIMO
After ending her relationship with Nate, a heartbroken Blair joined Chuck at burlesque club Victrola. Urged on by playful teasing from Chuck, Blair climbed the stage and performed her own sensual
-tease. But that’s not even the episode’s biggest shocker. Blair Waldorf, who had been saving herself Nate, swiped her V-card with Chuck Bass in the back of his limo. And thus the series’ most withstanding couple was born.
Viewers and Upper East Siders alike longed to know why Serena had run off to boarding school the year prior, and in the first season’s penultimate episode, the real reason was finally revealed: Serena had killed someone. Well… kinda. She has been with someone when they overdosed on drugs and felt like his death was her fault. So, like any rich kid is wont to do, she ran away and didn’t speak to any of her friends for a year.
BART DIED, WAS REVEALED AS ALIVE AND THEN DIED AGAIN
Midway through Season 2, Chuck abruptly lost his father when Bart died in a car crash. Three seasons later, Bart was discovered to be alive. You would think his renewed connection with everyone he left behind would melt his (non-existent) heart. But after Chuck discovered his father’s illegal activities (including murder), Bart attempted to have his son killed in a plane crash before fighting Chuck on a roof — set to the cheesiest soundtrack imaginable — and falling to his
In Season 2, it was revealed that Lily and Rufus had a child together 20 years prior. The pair managed to track down the adoptive family and learned that their son Andrew died. Except he didn’t. While Andrew was dead, their actual child Scott (Andrew’s brother) was very much alive. So, like any well-adjusted teen, he decided to move to New York and insert himself in his parents’ lives. After crashing their wedding and revealing his true identity, Scott finally got to spend time with his birth family — for a whole eight minutes. He was then never seen or heard from again.
Season 3 introduced a slew of new characters, but one of the most memorable additions was Hilary Duff’s famous actress Olivia Burke. Olivia and Vanessa were roommates at NYU, but would eventually go on to share something even more intimate, Lonely Boy. Yes, Lizzie McGuire had a threesome with two of the series’ most polarizing characters, in an episode the Parents Television Council wrote a lengthy letter urging The CW to rethink. While the actual scene wasn’t that racy — especially not by today’s standards — it was shocking that Dan, of all characters, would be involved in the tryst.
In the pilot, Jenny was charmed by Chuck Bass and accompanied him to the roof during the Kiss on the Lips party. Pouncing on Jenny immediately, Chuck tried to force her into a situation she clearly didn’t want before she was rescued by Dan and Serena. Cut to three years later when a sad, friendless Jenny found a heartbroken Chuck and decided she didn’t want to be alone. After the news of her tryst reached a distraught Blair, Little J found herself banished from the island of Manhattan.
Georgina was always full of surprises. Whether she was calling herself “Sarah” and blackmailing Serena, finding Jesus or showing up at NYU having turned over a new leaf (scoff), there was never a dull moment when G was in town. In the final moments of the Season 3 finale, Georgie showed up to remind everyone that she and Dan did in fact date at the beginning of the season and that she’s carrying lifelong proof of it. After a few weeks (three episodes, to be exact), Dan discovered that he is not Milo’s father, and Georgina and the baby disappeared into the
After Blair dumped him for sleeping with Jenny, Chuck headed to Prague to drown his sorrows, Chuck Bass-style. Walking through a seedy part of town, Chuck was ambushed by two thieves who discovered the engagement ring he had bought for Blair. Chuck attempted to bargain for it back, offering to take the thieves to an ATM and give them cash. But alas, his offer was refused: Chuck was shot and left for dead in the alleyway, and viewers were left to wonder about his fate all summer.
CHARLIE ISN’T CHARLIE, SHE’S IVY — LOLA IS THE REAL CHARLIE
saying something — the van der Woodsen/Humphrey gang was introduced to Lily’s niece Charlotte “Charlie” Rhodes. Except not really. They actually met an actress named Ivy Dickens who was introduced by Lily’s sister Carol as her daughter in an attempt to access Charlie’s trust fund. Things got even more complicated when Nate began courting cater-waiter Lola, who was in fact the real Charlotte Rhodes. You would think that would be the end of Miss Dickens, but alas, there is so much more to come…
CHARLIE ISN’T CHARLIE, SHE’S IVY — LOLA IS THE REAL CHARLIE (Cont.)
Lily and Carol’s mother Cece died and left her faux granddaughter her fortune using Ivy’s real name. Lola got into a war with Serena (who, it turns out, is her sister as well as her cousin, because of course she is), prompting Serena to reveal Lola’s parentage to Lily. Lola retaliated by giving Ivy her inheritance to take down Lily. Ivy, looking for her own revenge, shacked up with Rufus (!!) and William (aka Lola’s father) before attempting to trade incriminating evidence on Lily to either Chuck or his recently resurrected father.
There was no way this twist wasn’t making the list. A polarizing ending to say the least, we finally learned who Gossip Girl is in the series finale, and it was really… anticlimactic? After hiding in plain sight for years, it was revealed that Gossip Girl is in fact Lonely Boy himself, Dan Humphrey. The finale tossed around characters’ theories on who they thought it was all along — Eric! Dorota! — before jumping five years into the future and ending on a happy — if bizarre (Lily and William, really?!) — note.