"On the Upper East Side, it's easy to think that the world is exactly as it appears. Refined, elegant, imposing... But sometimes, all it takes is a little key to open the door to the wild side." - Gossip Girl
Serena, Blair, Nate, Chuck and the rest of their friends break into the school swimming pool for a night of fun, but when someone nearly dies, the school threatens to expel the person responsible for the break-in. Everyone agrees to keep silent, but this creates major problems between Serena and Dan, because Dan is not ready to take the fall for someone else and risk his future. While working on a documentary project about private schools, Vanessa accidentally captures Blair and Chuck discussing their affair. Meanwhile, Lily tries to tell Rufus how she really feels about him.
Memorable Quotes Edit
Dan: You really can be, damned if you do and screwed if you don't.
Gossip Girl: This just in. Nate Archibald. Dead man walking. We hear St. Jude's has a new policy. An eye for a lie.
Rufus: I'm still in love with you, Lily.
Lily: So what exactly are you offering, Rufus? Some retrospective of the way we were over a decade ago? We are not twenty and on the road.
Rufus: Thank god we're not! Because your mother made this decision for you back then, remember?
Rufus: Look, I don't know exactly what it would mean for us to be together, but can you look at me and tell me you're not the least bit curious.You're at the same crossroads you were years ago. Claim your life this time. Live it the way you want to live it.
Ms. Queller: I've already talked to your parents, at least those I could reach, and look forward to reading your personal essays. 10,000 words describing how you came to be on school property after hours, with alcohol and drugs, where a fellow student almost died. In other words: what the hell is wrong with you?
Blair: Do you think it's possible for two people who have been through as much as we have to really forgive and forget?
Nate: If we really want to, I think we can.
Blair: A lot of mistakes have been made.
Nate: If you're ready to forgive me then nothing can tear us apart. I promise.
Blair: If you didn't pay your rent with it, what did you do with Chuck's money?
Vanessa: I may have created a medical grant for teens with genital herpes. In his name.
Chuck (to Serena): Why don't I turn that one-piece into a no-piece?
Blair: Enough with the blackmail, aren't you bored already? I can't avoid Nate forever.
Chuck: I didn't say forever, just until the sight of you two together doesn't turn my stomach.
Blair: And when will that be?
Chuck: Only time will tell, I'm afraid. So unless you want dear Nathaniel to know how you lost your virginity to me in the back of a moving vehicle, I encourage patience and restraint.
Blair: Isn't there someone else you can torture?
Chuck: Probably, but I choose you.
Vanessa: So what will it be, Dan? Cheerios and Chaucer, or an illegal party at your prep school pool with your high society girlfriend and her nasty cohorts?
Blair(to Ms. Queller): I'm innocent. Well, except for a crime of passion. I did something stupid with someone and even worse than doing that stupid thing I did the same stupid thing with someone else and pretended I had never done that stupid thing before. You look confused, should I walk you through it?
Blair (to Serena,about Vanessa): You are so naive. Michael Moore over there is obviously just using this film to get close to Dan.
Chuck(to Serena): You know, if my dad and your mom come back from South Africa tomorrow engaged we'll be brother and sister. And you know what they say, the family that plays together stays together.
Serena: Ah. Incest, the universal taboo. One of the only ones you haven't violated.
Chuck: I'm game if you are.
Dan: You need to tell the truth.
Chuck: What happened to 'don't speak until spoken to'?
Dan: I just saw you with that key. I know you had it at the party
Chuck: Poor little Humphrey Dumpty. Look, let me clarify something for you. Regardless of who you're currently sleeping with, you and I come from different worlds. In my world, if I'm suspended or expelled, a wing is donated in the Bass name.
Dan: That does sound like quite a world.
Chuck: It's not perfect, I'll admit but one thing is does offer in spades is security. My family can take care of me. What do the Humphreys have to offer? Used metro cards? Your dad's cassingle?
Chuck (to Vanessa): Blair is an amateur. She thinks you're just like her. To Blair, this means a couple pairs of Manolo's and a Chanel bag, but I know that this much cash could make a real difference in your life.
Gossip Girl: Spotted: Lonely Boy learning that when the punishment fits the crime, there's no reason you can't serve your sentence in style.
Gossip Girl: There's a weak link in every chain, and it's just a matter of time before this one snaps.
Gossip Girl: Who knew B and C were such patrons of the arts? Call it philanthropy or bribery, it looks like everyone has their price.
Chuck: How glad are you that our two families are merging together, sis?
Serena: So glad that if you ever call me that again, it will be the last thing you ever say, Chuck.
Blair : You just won 365 more days in your Ikea-furnished closet.
Vanessa: You went to my building? You talked to my landlord?
Blair: No, I don't speak Ukrainian, but I do speak envelope of cash and he understood me perfectly.
Gossip Girl: One thing about being on the inside, once you get there, you don't always get to choose where you stand,or sit.
Gossip Girl: Sometimes you need to step outside, clear your head and remind yourself of who you are. And where you wanna be. And sometimes you have to venture outside your world in order to find yourself. As for me, I'm happy right where I am. I only wanna be with you.
Chuck: A heartfelt letter? Who spayed you, man? Blair doesn't even want you, she's been crystal about that since we got back.
Nate: Didn't seem that way when she kissed me at the pool.
Bart: So. Your new step-brother told me about your problem at school. Frankly, I wasn't surprised given your propensity for recklessness and adventure.
Serena: I'm sorry?
Bart: Don't tell your mother, but... I made a call.
Serena: You did what?
Bart: It was harder than usual. That new headmistress of yours is a new piece of work. I had to go over her head. Sorry I couldn't get the charges completely dropped, but, at least I got you minimal sentence.
Chuck: I was just looking out for my family. The new Van Der Woodsen-Bass library should be completed for Eric's graduation.
Chuck: Drop your Archibald habit first.
Blair: You know I already have.
Chuck: Really? A kiss does sort of send the wrong signal. Lets not waste time denying.
Blair: You know what? I'm tired of this. Go ahead and tell him.
Chuck: Really? You want me to tell him how you slept with me and then faked your virginity for him?
Blair: I'll just tell him you're lying. And who do you think he'll believe? You who bangs anything in his field of vision. Or me, his pure and honest girlfriend of many years.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Taylor Momsen as Jenny Humphrey
- Ed Westwick as Chuck Bass
- Chace Crawford as Nate Archibald
- Jessica Szohr as Vanessa Abrams
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Kristen Bell as Gossip Girl
Special Guest Stars Edit
- Jessica Szohr as Vanessa Abrams
- Robert John Burke as Bart Bass
- Linda Emond as Headmistress Queller
- Nicole Fiscella as Isabel Coates
- Connor Paolo as Eric van der Woodsen
- Nan Zhang as Kati Farkas
- Amanda Setton as Penelope Shafai
- Dreama Walker as Hazel Williams
- Reed Birney as Mr. Prescott
- "Last Night (Oh Yeah)" by Moby
- "Someone Great" by LCD Soundsystem
- "Come Flash All Your Ladies" by The Filthy Youth
- "Orange" by The Filthy Youth
- "Autumn Pink" by Harry Warren
- "Breakfast In NYC" by Oppenheimer
- "Come Home" by OneRepublic
- "Four Romantic Pieces, Opus 75" by Dvorak
- "Piano Quartet in G Minor" by Mozart
- "Cross The River" by La Rocca
Cultural References Edit
- Chanel - Chuck references this high-end fashion brand when he says $10,000 for Blair is just a Chanel bag
- Cornell University - Blair says that Kati and Is made out with a guy from Cornell's ethics programme
- Geoffrey Chaucer - Vanessa mentions this poet when she says to Dan "Cheerios and Chaucer".
- Manolo Blahnik - Chuck references this high-end shoe designer when he says that $10,000 for Blair is just a couple of Manolo shoes.
- Michael Moore - Blair nicknames Vanessa after this american filmmaker
- Le Bilboquet - Blair mentions this french restaurant
- South Africa - Bart and Lily are on vacation there
Food & Drink Edit
- Cheerios - Vanessa records Dan eating a bowl of cheerios cereal at night