The Craziest Things That Happened in the Gossip Girl Pilot
By Alexus Mosley
In 2007, Gossip Girl introduced us to Manhattan’s elite with one simple announcement. Serena van der Woodsen had been spotted at Grand Central, and what followed was approximately 42 minutes of secrets, scandals, broken relationships, and enough family drama to fill an entire season.
Serena returned from boarding school, Nate confessed to sleeping with his girlfriend’s best friend, and Little J made her first attempt at entering Upper East Side society. If that weren’t enough to make things juicy, we learned that the parents were almost as messy as their children.
Nearly two decades later, we went back to where it all began. Here are some of the craziest things that happened in the Gossip Girl pilot.
Serena Returned to Manhattan Without Telling Anyone
After mysteriously leaving for boarding school, Serena returned to New York without telling even her best friend. Unfortunately for Serena, keeping a low profile wasn’t exactly an option. One sighting at Grand Central was enough for Gossip Girl to announce to the entire Upper East Side that S was back.
We Learned Serena Slept With Nate
And suddenly Serena’s disappearance made a lot more sense.
Before leaving Manhattan, Serena slept with Nate Archibald—her best friend Blair’s longtime boyfriend. Instead of saving the revelation for later, Gossip Girl dropped one of its biggest secrets in the very first episode.
Nate Confessed to Blair at the Worst Possible Time
Blair’s Father Left Eleanor for a Male Model
Blair wasn’t only dealing with Serena and Nate. We also learned that her father, Harold, had recently left her mother for another man, a male model named Roman. The Waldorf family drama was already well underway before we arrived.
Lily Was Keeping Eric’s Hospitalization Quiet
Serena’s real reason for returning to New York was her younger brother, Eric, who was receiving treatment after a suicide attempt.
Meanwhile, Lily was determined to keep the situation private. It immediately establishes one of the van der Woodsens’ recurring conflicts: maintaining the perfect family image when things behind closed doors are anything but.
Alison Humphrey Left Her Family for “Art”
The Upper East Siders weren’t the only ones with complicated families.
Dan and Jenny’s mother, Alison, was living in Hudson to focus on her art, leaving Rufus in Brooklyn with their children. The Humphreys were introduced as outsiders looking into Manhattan’s dysfunctional elite, but things weren’t exactly perfect at home either.
We Learned Rufus and Lily Had a Past
Before Dan and Serena could even get their relationship started, we learned their parents had already been there.
Rufus and Lily’s interactions make it clear that the two share a romantic history and perhaps some unresolved feelings. Apparently, the Humphrey–van der Woodsen connection started much earlier than Lonely Boy realized.
Dan Got a Date With Serena Almost Immediately
Dan had admired Serena from afar for years, while Serena barely knew who he was.
Yet shortly after she returned to Manhattan, a conveniently forgotten phone brought them together, and Dan suddenly had a date with the most talked-about girl on the Upper East Side.
Lonely Boy didn’t stay lonely for long.
Chuck Attempted Sexual Assault Twice
One of the most disturbing parts of the pilot is Chuck’s behavior toward both Serena and Jenny. He attempts to sexually assault Serena earlier in the episode and later attacks Jenny at the Kiss on the Lips party before Dan intervenes.
The scenes are particularly jarring in retrospect, considering Chuck would later become one of the show’s central characters and romantic leads.
Dan Punched Chuck
After realizing Jenny was in trouble at Kiss on the Lips, Dan and Serena rushed to find her. Dan confronted Chuck and punched him before leaving with Jenny and Serena.
Dan’s first real introduction to Upper East Side society certainly wasn’t subtle.