Pilot is the 1st episode of the first season and the 1st episode overall. It serves as the Pilot episode for the whole series.
|“||Hey, Upper East Siders, Gossip Girl here, and I have the biggest news ever. One of my many sources, Melanie91, sends us this: "Spotted at Grand Central, bags in hand: Serena van der Woodsen." Was it only a year ago our It Girl mysteriously disappeared for "boarding school" and just as suddenly she's back. Don't believe me? See for yourselves. Lucky for us, Melanie91 sent proof. Thanks for the photo, Mel.||”|
— Gossip Girl
Gossip Girl is busy spreading the news that "It Girl" Serena van der Woodsen has returned to Manhattan after a mysterious and seemingly self-imposed exile to boarding school. Serena's best friend, Blair Waldorf, seems to have conflicted feelings about her friend's return, since she has enjoyed being Queen Bee during Serena's absence, and might not be ready to relinquish her new position on the social ladder. Blair also suspects that there may be secretive and unspoken feelings between Serena and her longtime boyfriend, Nate Archibald.
On the Upper East Side in Manhattan, Serena van der Woodsen arrives at Grand Central Station. Gossip Girl, voiced by Kristen Bell, narrates her arrival, crediting 'Melanie91' for snapping a picture of Serena, who is suddenly back from "Boarding School" after a year away from the city. Simultaneously, Dan Humphrey and his younger sister Jenny are also at Grand Central as they return from a weekend visiting their mother in Hudson. They are welcomed by their father, Rufus, who immediately asks if the siblings' mother regrets leaving Manhattan. It is revealed that the Humphreys' marriage is in disarray. As they leave the station, Dan gazes longingly at Serena, and Gossip Girl narrates her first 'Lonely Boy' post.
The news of Serena's arrival quickly spreads, as different people all over the city are shown receiving notifications about the news through their phones. At a party attended by most of Serena's old friends and their families, it is explained that Blair's mother is a fashion designer. At the same time, Nate Archibald's father introduces him to some of his friends as a future Dartmouth student. Nate mentions that he would like to also consider some colleges on the west coast, but his father tries to convince him that Dartmouth is the best option. Suddenly, Blair interrupts their conversation, and takes Nate to a bedroom insisting that she's ready to have sex, despite having previously told him that she wanted to wait. On their way to the bedroom, Charles "Chuck" Bass is introduced, as he asks Nate if he wants to accompany him to "get some fresh air" (in this case, he's referring to smoking marijuana.)
Whilst Blair and Nate are in the bedroom, Serena is shown arriving to the party. She is greeted by Blair's mother, Eleanor Waldorf, who immediately calls out to Blair about Serena's arrival. Nate hears that Serena has returned, and, despite Blair's protestations, rushes out of bed to see her. Serena searches for her mother, Lily Van der Woodsen and asks where her younger brother Eric is, but her mother doesn't want to talk about it in public. As Nate walks out of Blair's room, he catches Serena's eye and smiles at her, but Blair quickly gets between the two of them. She greets Serena with a fake smile and a hug and insists that she stays for dinner, but Serena excuses herself by saying that she doesn't feel well and that she'll see Blair at school the next day. Blair is offended by Serena's abrupt departure, and begins talking to her other friends. Gossip Girl narrates her surprise at Serena's refusal to stay, noting that the "bad girl" might have really "gone good." Dan is shown reading the Gossip Girl posts about the party on his laptop at home.
Serena then goes to the hospital to visit her brother Eric, spending the night on the chair next to his bed. In the morning, Eric wakes his sister, and the two embrace as Serena apologises for not being there for him. Lily arrives, and is quickly confronted by Serena. It is revealed that Eric's stay in the hospital is related to a suicide attempt. Serena is furious when Lily explains that she has been hiding Eric's condition, using the excuse that he is actually in Miami visiting his Aunt Carol in order to protect her reputation. Lily rebukes Serena, indirectly implying that she does not believe that she has changed whilst away at boarding school, and that she is still tainted by her former party-girl, wild-child image. Meanwhile, at the Humphrey residence in Brooklyn, Rufus tells his children about his former band, Lincolnhawk, and the fame they achieved in the 90's. Jenny finishes her calligraphy for the notorious 'Kiss on the Lips' party invitations, and explains that she traded her art skills for an invite to the party itself, which is an exclusive and very popular event.
At The Palace Hotel, Nate is seen waiting for Serena to arrive. It is revealed that Serena's family are currently staying at the hotel whilst their apartment is being renovated. He tries to begin a conversation about why Serena was upset last night, but she quickly changes the subject and says she has to get ready for school. When he continues to follow her, she explains that she never came back for him. She states that Blair is her best friend, and that Nate is her boyfriend and that's how things are supposed to be. She walks away, leaving a hurt-looking Nate alone.
Dan is then seen rushing through traffic to catch his bus to school. It is shown that Chuck and Nate, who are two of Dan's classmates at St. Jude's School for Boys, are also on the bus. Chuck, quite vulgarly, comments on Serena's appearance the night before, and teases Nate for not having had sex with Blair yet, even though they've practically been dating since kindergarten. As they arrive at school, Chuck notices Dan behind him, and rudely questions whether he is following them. Dan replies sarcastically, stating that they go to the same school, and are wearing the same uniform, which should be "kind of a tip off."
Before school begins, Jenny is shown hand-delivering the invitations to the 'Kiss on the Lips' party to Blair and her minions, Kati and Isabel, on the steps of the Met. Serena arrives and introduces herself to Jenny, enquiring about the invites. Blair dismissively tells Serena that since she only arrived in the city 12 hours beforehand, she's not invited due to lack of space. As they go their separate ways, Serena asks Blair if they can meet at The Palace Hotel at 8pm. Blair says that she has a date with Nate, but Serena insists that he will wait. Gossip Girl narrates the scene, terming it "an S and B power struggle."After school, Dan is seen helping Rufus post flyers for his band's concert tonight, when he gets an emergency text message from Jenny. Rufus, clearly preoccupied with thoughts of his estranged wife, distractedly tells Dan that he can go, and join him again later. Dan rushes to Jenny's aid, and it turns out that she is just trying on dresses for the 'Kiss on the Lips' party, hoping to find the perfect outfit that she can replicate by sewing it herself when she gets home, since she can't afford to buy the real thing. Dan is disgruntled at first, but supports his sister. Suddenly, Jenny spots Serena, who has snuck her brother out of the hospital in order to go shopping at the mall. Jenny reaches into her bag to give Serena an extra party invite she made after the scene with Blair. Meanwhile, Dan hides behind racks of clothes in order to avoid Serena, and eventually creeps away. In Central Park, Nate and Chuck take a stroll whilst openly sharing a joint. Nate shares his feelings about living a life that seems to be planned out for him by his parents. Chuck advises him to simply get high and have sex with Blair.
Blair and Serena attend their scheduled meet-up, and are seen drinking at the bar of the Palace Hotel. Serena asks how Blair's mother is handling the divorce she is going through, so Blair discloses that her father actually left her mother for a man. Blair is resentful that Serena didn't tell her why she went to boarding school in the first place, and is angry that her supposed best friend had not been there for her. Serena acknowledges that Blair is the new Queen Bee at school, and says she's not interested in stealing that role from her. Eventually, the tension fades away, and the two exchange a warm hug as they agree to begin again with their friendship. However, when Blair leaves for her date with Nate, Serena is seen drinking the rest of Blair's drink, prompting Gossip Girl to narrate that Serena may still be hiding something.
At the Humphrey Residence, Jenny chats to Dan whilst sewing her dress for the party. The pair talk about Dan's crush on Serena, with Dan stating that his un-glamorous life in Brooklyn would never be interesting enough for Serena van Der Woodsen to care about. Jenny counters by telling him that Serena is probably at The Palace Hotel all alone. This image forces Dan to go out and visit Serena. However, before he arrives, Chuck approaches Serena at the bar of the hotel and begins to flirt with her. She's not in the mood, claiming that she's been drinking on an empty stomach, so Chuck offers to get her a grilled cheese from the kitchen, as he says his parents own the hotel.
In the meantime, Nate enters his bedroom to find Blair already waiting for him in sexy lingerie. She has decorated the room romantically, as she is expecting anticipating having sex with Nate for the first time. Blair begins to kiss Nate, but he doesn't kiss her back, and it is quickly revealed that he feels guilty about the events of the notorious 'Shepherd Wedding', as he explains to a heartbroken Blair that he had sex with Serena on an empty bar during the wedding. Blair is crushed, and tells Nate to leave.
Back in the hotel kitchen, Chuck gives the the kitchen staff the night off. He makes advances towards Serena, but she tells him it's not going to happen. In response, Chuck tells Serena that he knows what she did at the Shepherd Wedding, and subsequently knows why she left town. A flashback sequence shows a drunk Serena dancing on top of a bar, whilst Nate laughs with her and cracks open a bottle of champagne. They begin to kiss, and eventually end up having sex, all of which is witnessed by Chuck. The flashback ends, and Chuck corners Serena in the kitchen and attempts to start kissing her again, but she fights against him and runs away. On her way out, she bumps into Dan and her purse gets knocked to the ground. Dan apologises and helps her, but she ignores him and carries on her way out. Dan notices that she left her cellphone behind, but by the time he picks it up, Serena has hastily left.
The next morning, Nate and his dad are running together in the park. Nate tells him that he had a big fight with Blair and they've practically broken up. Nate's father disapproves of this, and wants them to get back together, mostly because it would help him advance in relation to business deals with Blair's mother. Although Nate seems to feel the split with Blair is not an entirely bad thing, his father begins to put pressure on him to repair the damage in order to cement his business dealings, telling him his family "is depending on him."
At The Palace Hotel, Dan tries to return Serena's cell phone, but the concierge is suspicious, and calls Serena over to ask if she knows Dan. Dan is mortified, until Serena states that she does recognise him from the previous night, which he is rather surprised about. Suddenly, Serena's mother interrupts the pair as she brings Serena a dress for her to wear to the 'Kiss On The Lips' party. However, the tension with Blair, and Chuck's revelation, Serena decides that she no longer wants to go. She makes up an excuse that she has plans with her "new friend" Dan to see a Lincolnhawk concert that evening instead. When Serena's mother leaves, Dan walks away, but to his surprise, Serena takes him up on the offer of the concert, and asks him to pick her up at 8pm.
Later on, Nate and Blair are seen eating sushi together at a restaurant. Nate has arranged the meet-up in order to apologise to Blair. He promises that he'll never talk to or see Serena again, saying that it will "be like she doesn't exist." Blair is startlingly quick to forgive Nate, stating that what happened in the past is in the past, and that she trusts that he has no feelings for Serena anymore.Meanwhile, at Rufus's art gallery, Lily arrives to question him on why her daughter is going to one of Rufus's band's concerts with his son, Dan. Rufus is surprised that Dan scored a date with Serena, leading Lily to accuse Rufus of using Dan to get to her because of the breakdown in his marriage. Rufus is flirty, comparing Lily to how she was back in the "old days." It appears that the two knew each other beforehand, as Rufus states that Lily moved on from rock stars to billionaires to sustain her luxurious lifestyle. Lily then tells Rufus to stay out of her life, and leaves.
Back at the Humphrey loft, Jenny is getting ready for the 'Kiss On The Lips' party, and Dan is getting ready for his night out with Serena. Jenny is proud of them both, as she remarks, "who said this family wasn't cool?"At the Waldorf penthouse, Blair is also getting ready for the party, by trying on a dress in front of her mirror. Her mother gives her some advice about her appearance, and is as loving as she is critical.
On the way to the party, Blair, Nate, Chuck, and their friends are seen partying, drinking and smoking in the back of a limousine with bottles of champagne. Dan, meanwhile, arrives at The Palace Hotel to pick up Serena, and once again glimpses her above him on the balcony looking beautiful. Once everyone else arrives at the 'Kiss On The Lips Party', Chuck notices a "newbie" - Jenny. She is a freshman, and Chuck sets his sights on seducing her rapidly. She is young and flattered by his not so innocent intentions. Dan and Serena are then shown walking to the concert when Dan spots his Dad, and introduces Serena to him. She laughingly questions Dan about why he introduced his Dad to her on the first date, at which point Dan asserts that their night out together is indeed, a 'real' date. Meanwhile, at the party, Chuck entices Jenny to a private stairway under the guise of wanting to get to know her better in a quieter space, but as they ascend the stairs, Chuck tries to kiss her. Jenny is reluctant, so Chuck apologises and asks if they can start over. He offers her a glass of champagne, and she agrees, but texts Dan asking for his help because she doesn't feel safe when Chuck refuses to go back to the party with her.
Dan and Serena leave the concert, at which point he receives the text from Jenny. Serena, aware of the seriousness of Chuck's predation, offers to help him find her, and together they enter the 'Kiss On The Lips' party in order to find Jenny. Blair is furious that Serena would gatecrash her party, but before she can kick her out, Nate tries to convince her not to. Blair and Serena exchange eye contact across the dance floor, in a way that seems to suggest to Serena that Blair finally knows about what she did with Nate.
Eventually, Dan and Serena search upstairs, where they find Chuck forcefully attempting to kiss Jenny, as she is pinned down by him and begging him to stop. Dan, in his rage, punches Chuck in the face, and Serena warns Chuck to never touch Jenny again. As they leave, Chuck threatens Serena, calling her a slut, and reminding her that he knows everything. As they leave the party, Dan holds his sister's hand, and Serena in turn grabs Dan's, as guests look on in amazement. He enquires about a second date with Serena, and the episode then ends with Dan, Serena, and Jenny heading home in a cab together, whilst Blair and Chuck watch with expressions of anger and disgust.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald
- Taylor Momsen as Jenny Humphrey
- Ed Westwick as Chuck Bass
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Nan Zhangas Kati Farkas
- Sam Robards as Howie "The Captain" Archibald
- Connor Paolo as Eric van der Woodsen
- Florencia Lozano as Eleanor Waldorf
- Nicole Fiscella as Isabel Coates
- Anthony Stewart-Jones as Concierge
- Jessica Andres as Girl #1
- Jackie Moore as Halfnude model
- Lindsey Evans as Dominique
- Robert Gordon as Family Guest
Isabel - "Someone saw Serena get off a train at Grand Central."
Chuck - "Good, things were getting a little dull around here."
Chuck - "Serena looked effing hot last night. There's something wrong about that level of perfection, it needs to be violated."
Nate - "You are deeply disturbed."
Lily - "You think you're so cute. Washed up band, crappy so-called 'art gallery'".
Rufus - "Well, not all of us have settlements from multiple divorces to sustain us."
Chuck - "What we're entitled to is a trust fund, maybe a house in the Hampton's, a prescription drug problem, but happiness does not seem to be on the menu."
Dan - "You'd really go out with some guy you don't know?"
Serena - "Well, you can't be any worse than the guys I do know."
Eleanor - "Blair, you will never be more beautiful, or thin, or happy than you are right now. I just want you to make the most of it."
Chuck - "Are you following us or something?"
Dan - "No, I go to your school. Identical uniforms, that's kind of a tip off?"
Chuck - "I'm going to have to tell my parents the hotel they just bought is serving minors."
Serena - "And if you get a drink, they're also serving pigs."
Chuck - "Ooh, I love it when you talk dirty."
Serena - "You just love it when a girl talks to you."
Chuck - "Actually, I prefer them when they're not talking."
- This is the only episode that Nate and Chuck ride a public bus to school.
- This is the only episode where Florencia Lozano acts as Eleanor - in the rest of the episodes, she is played by Margaret Colin.
- This is the second highest-rated episode in the series.
- Cabbage Patch Kids - Dan owns a cabbage patch kid named Cedric.
- Cinderella - Dan mentions the fairy-tale when he argues with the concierge at the Palace Hotel, stating that "when Prince Charming found Cinderella's slipper, they didn't accuse him of having a foot fetish."
- Henri Bendel - Serena says to Eric that she wants to go shopping at Bendel's, a huge department store selling upscale women's clothing in Manhattan.
- MySpace - When Rufus staples flyers around town about his band's performance, Dan says that "there's a place called MySpace, where you can post all this information online, save some trees, make a blog."
- Rolling Stone Magazine - A popular music publication that Rufus shows to Dan & Jenny when his band is featured in an article entitled, "Top 10 Forgotten Bands of the 90's"
- Socrates - Chuck jokingly compares Nate to Socrates (an ancient Greek philosopher) after Nate expresses his worries about his future being planned out for him by his parents, and whether that future might include happiness.
- Takashi Murakami - A famous artist known for his work in painting, sculpture and fashion, and blurring the boundaries between so-called "low" and "high" art. This is who Lily is referring to when she says, "I don't care if it's Murakami, it clashes with my sofa."
- Trent Reznor & Nine Inch Nails - An American industrial-rock band that came to popularity in the 1980s and throughout the 1990s. Reznor is the founding member and lead vocalist of the band, and Rufus says that he recalls Lily being at the back of the Nine Inch Nails bus with him.
- Gilt - The name of the bar that Serena and Blair meet at. It's located inside The Palace Hotel, and is a real bar that members of the public can visit. 
Food & Drink
- Caprese salad with mozzarella di Bufala - A simple salad dish with tomato, basil and olive oil dressing. Rufus says he's going to make this for Dan and Jenny at home. 
- Champagne - First shown during the flashback of Serena and Nate at the Shepherd wedding. Chuck Chuck later offers Jenny a glass of champagne in an attempt to get her drunk at the 'Kiss On The Lips' party.
- Croissant - A sweet, French pastry often eaten for breakfast. Referenced when Serena invites Lily to join her and Eric for a breakfast outing, and Lily just wants to go and get him a croissant from "down the street."
- Green Jello - The American term for basic gelatin or 'jelly' desserts. Referenced when Eric says to Serena, "they had this green jello for lunch", to which she replies sarcastically, "yum, why didn't you save me any?"
- Grilled Cheese Sandwich with Truffle Oil - A dish that Chuck offers to Serena from the Palace kitchen, when he recalls that she loves truffles. The dish is not on the menu, but Chuck's connections mean he is able to ask the Chef (who is played by actual celebrity chef Christopher Lee, in the episode) to make it especially for her. Truffles are a type of fungi-vegetable notorious for being glamorous and very expensive. Truffle oil is a cooking oil deriving its aroma and flavours from the truffle plant, and can be added to any dish. The exact recipe for the grilled cheese that Serena eats in this episode can be found here: 
- Limoncello - A traditional Italian liqueur made from sugar, syrup, lemons and lemon zest. The drink is mentioned when Gossip Girl narrates,"word is that S bailed on B's party in under 90 seconds, and didn't even have one limoncello."
- Martini - A highly-popular cocktail made from gin and vermouth and often garnished either with an olive or a lemon twist. The drink became truly famous during the Prohibition era of the 'Roaring '20s'. The word 'martini' can also be used to refer to the specific glass used to serve the cocktail. In this episode, Blair is seen drinking a martini whilst talking to Serena, and when Blair leaves, Serena finishes the rest of it herself.
- Sushi - A Japanese style of food preparation often containing raw seafood, vinegar-soaked rice and vegetables. Blair and Nate are seen eating sushi together at a restaurant for lunch when they meet in this episode.
- Yogurt - A dairy snack that Serena and Katie are seen both eating before school, when Blair says to Serena, "we should get going then, unless you want us to wait for you...but itlooks like you've got a lot of yogurt left.'