Eric: Well I found it. And just in time: the car’s here. Now it’s time to go… get you dressed.
Jenny: No, I’m not leaving.
Eric: I don’t think we have a choice.
Jenny: As soon as we get in that car that means no more beaches and no more bonfires and no more stalking the Barefoot Contessa through 1770 House. Our summer in the Hamptons is officially over.
Eric: So, uh, a sit in.
Jenny: More like a lie-in. At least until the sun goes down.
Eric: You sure your dad doesn’t know?
Jenny: No, totally. I mean, we hid all the evidence. Look, Dan doesn’t even know. He was prereading all his books for college. And I snuck onto his laptop and might have disabled his Serena van der Woodsen Google Alert.
Eric: But what happens when we get back to the city?
Jenny: Then it’s Serena’s problem. As for now we made her a promise. And it is very important to keep those. Even if they were asked via drunken text from a Turkish pay-as-you-go phone.
Serena: What’s that?
Rufus: The money your mother left us for emergencies. Not to boast but we haven’t used a penny of it all summer.
Jenny: Well thank heaven for salaried servants and an account at the beach club, right.
Rufus: Well I’m glad I have the number for City Harvest. This is all a little much.
Dan: A little much? It makes the Four Seasons look like… one season.
Rufus: I don’t understand. Serena’s arrest was months ago. Why do they still care about her so much?
Eric: Her hair.
Jenny: Her clothes.
Jenny: Her hair.
Eric: Her hairstyle.
Rufus: What do you know that I don’t know?
Eric: “Mrs. Jennifer Humphrey”. When did you get married?
Jenny: It doesn’t matter. It’s engraved.
Jenny: Dad, Scott’s been spending a lot of time here lately.
Rufus: Yeah he’s a good kid. Good guitar player too.
Jenny: Hi. Who are you?
Carmen: I’m Carmen. This is Celeste. That’s Jane. We’re here to make sure you get exactly what you want this year.
Celeste: You’re going to rule the school with an iron fist.
Jenny: Okay enough. First go wash your eyes. And second, tell everyone I need to talk to them now. Now.
Eric: So. A new era of sunlight and fairness.
Jenny: There is no more hierarchy. The steps of the Met will no longer be restricted to a certain crowd. No more Nairtinis. No more headbands. This is a new era. Let freedom reign.
Jenny: What is this? Did you not hear me this morning?
Carmen: Oh, you mean your cute little attempt at Perestroika?
Jane: We’re going back to the old way. Queens, hierarchy and no Brooklyn wannabe’s.
Jenny: Congratulations. Your girlfriend’s installed a puppet regime.
Chuck: Blair’s gone Colonel Kurtz. She needs to be brought back to reality. Help me. And I’ll help you take back the crown.
Jenny: Why? They don’t want my kind of leadership. They want a tyrant who will police their behavior and chart their movement on the social ladder. Find someone else.
Chuck: I need you. You’re fooling yourself if you don’t think you were born to rule this school.
Jenny: People change, Chuck.
Chuck: Not you. Not about this. Jenny Humphrey who used to sit in Brooklyn and watch the lights across the water. Who went toe-to-toe with Blair Waldorf and actually won her respect. You can’t tell me that girl’s not still in there.
Serena: Hey, what’s going on with mom and Rufus?
Jenny: You don’t know? They’ve been in a cold war since the day you left.
Serena: Over Brown?
Eric: On the surface, yeah. But I have a feeling mom’s flipping out over other things too.
Jenny: I think they could be in real trouble.
Lily: You’re kidding.
Rufus: I knew I let you kids watch The Parent Trap too many times.
Dan: It’s time for you two to talk.
Jenny: You love each other.
Serena: And it’s not Rufus’ fault I made the decision not to go to Brown.
Eric: Can you please sit down? For us.
Lily: Well I do love the bolognaese here.
Jenny: You know, Lily, it wasn’t easy for me when my parents split up. And it was even harder when I realized my dad was in love with someone else. But the truth is I’ve never seen him happier than he is with you.
Lily: That is so sweet.
Jenny: I can’t wait for you to hear his vows.
Scott: Sorry for not telling you who I was.
Dan: You know, I should have guessed. No one under forty has ever shown that much interest in Lincoln Hawk.
Jenny: See, I told you. He has my nose.
Eric: Maybe. But those are my eyebrows.
Jenny: So Scott, what do you think about board games?
Scott: Love them.
Dan: We just started dating. Isn’t it a little soon for “Meet the Parents”?
Vanessa: Not for Olivia. She seems really easygoing and into you.
Jenny: Yeah. Seriously Dan. Play the parent card. People like you more when they meet your family.
Eric: So Rufus asked my size this morning. Does this mean I’m getting a flannel?
Jenny: No. He’s just a costume enthusiast. He likes Halloween more than he likes Christmas and his birthday. So we have to find a party otherwise I swear he’s going to make us hand out candy dressed as the Octo Babies.
Jenny: Not bad. But it’s Prohibition. Not Last of the Mohicans.
Jenny: I don’t know why he’s blaming me. I didn’t do anything. I can’t control every girl at school.
Lily: Oh Jenny. You and I both know that that’s not true.
Jenny: You know I have to act this way about school stuff. But I’m still your friend, I’m still your sister. We just can’t let the worlds get confused.
Eric: I’m not confused. I want nothing to do with you in either world.
The Grandfather: Part II
Eric: It helps if you count out loud.
Jenny: Eric you don’t have to be nice to me. I’ve been so awful to you and Jonathan.
Eric: It’s true. But I’m a better person than you are.
Jenny: That’s also true.
Jenny: Look, I have enough of my own problems, so I’m not going to let you guys make me a pawn in your war.
Blair: Jenny, you’re lucky to have me. Don’t push it.
Jenny: Your era’s over. And so is that headband.
Lily: What about Brad Alexander? His mother said he’s single.
Jenny: Ah, yeah, Because he gave six girls from Nightingale gonorrhea of the throat last year.
Jenny: So Belgium, huh? I bet they have really good waffles. My family’s really into waffles.
Damien: Yeah I barely tasted them. My father left when I was four so he could work on the Oslo Accord.
Jenny: He worked on the Oslo accord? That sounds major.
Damien: Yeah, clearly more major than being a father, but…
Damien: What exactly does an Upper East Side Queen do? Wear designer clothes, boss people around?
Jenny: No. I go to parties and openings and stuff.
Damien: Where you wear designer clothes and boss people around. Sounds like kind of a yawn.
Jenny: Well yeah, I guess compared to being the international drug dealer.
Jenny: I’m going to go use the restroom.
Damien: No, sit down.  hand in here. And just test the product, yeah?
Chuck: That won’t be necessary.
Jenny: Chuck, what are you doing here?
Chuck: I got your message. Had housekeeping do an early turndown service on Damien’s room. That’s where they found his stash. I have my own experience in the ball pond. I’m taking you home. You and your father have until noon to collect your luggage. After that it’s in the river.
Jenny: Chuck, you’re totally overreacting. I’m really fine.
Damien: Dude, the lady said she’s fine.
Chuck: Dude. I’m Chuck Bass. Even Europeans must know what that means.
Chuck: Look, I get the whole “sullen teenager pushing the envelope” thing. I pushed a pack. But you’re better than that Damien guy.
Jenny: Look, I may be queen but I’m more lonely and bored than I was when I lived in Brooklyn. And being with him is exciting.
Chuck: And dangerous. Please. It takes one to know one. I saw that look in your eye the very first day you came on my radar.
Jenny: And what so-called look would that be?
Chuck: Be very careful, Jennifer Humphrey. If you go down the rabbit hole, it’s going to take more than Blair Waldorf and her army of minions to drag you back out.
Jenny: So what, are you going to walk me to my room and make sure I don’t get into any trouble?
Chuck: Just try not to run into any drug dealers in the kitchen.
Vanessa: Why does my mom have to stick her nose in everyone’s business?
Dan: C’mon, Cece’s heart pumps secrets and gin. It’s not your mom’s fault.
Vanessa: You’ve been defending her all day. You’re worrying me. What’s going on with you? And you’re making that face again.
Dan: No- Alright, look. This is getting ridiculous.
Vanessa: Jenny have you ever heard of someone starting to make a brand new face at 19?
Jenny: I don’t know. Ask Eric. He’s mastered two.
Eric: Excuse me?
Jenny: Blair told me you were responsible for sabotaging me at Cotillion. What? You have nothing to say to me?
Eric: Your sweet potatoes. Are bland.
The Hurt Locket
Lily: So how was your mom’s? I’m sure your dad called every day.
Jenny: Well he v-chatted for present opening. You didn’t want to go to Telluride with him, huh? I can’t say I blame you. Those Lincoln Hawk guys can be kind of annoying.
Lily: Well he was so excited when it came up I couldn’t stand for him to miss out.
Lily: So. Your father and I haven’t really discussed you having boys alone in your room. So maybe just keep the door open?
Jenny: Lily, if we wanted to have sex we’d just go to a hotel. And seriously, it’s not like that with us.
Lily: Well what is it like? I mean he seems happy to see you—
Jenny: I’ll open the door if anything changes.
Lily: Oh! And you wouldn’t happen to know when your father was coming back? Larissa accidentally lost the itinerary.
Jenny: I think he said today, but just… call him and ask.
Jenny: I can wear it. I can make this only in mine the pailettes won’t be empty.
Damien: You put the pills in the jacket?
Jenny: Yeah. I wear it to the dinner, check it, and then Violette and I switch coat check tags. I take her coat—
Damien: —and she’ll leave with yours. That’s not bad.
Jenny: Not bad! C’mon, it’s brilliant.
Damien: We’re going to have to do our little dinner some other time.
Jenny: What? I thought we were going to do this together. It’s my plan.
Damien: Yeah. And I thank you. It’s just that… anyone can check the jacket. Jenny’s not buying it. Um… I’m going with someone else. Serena, actually. We’re old friends from boarding school.
Jenny: Serena’s with Nate now.
Damien: I don’t know about that. She’s the one that called and asked me.
Jenny: Well you know she’s changed since boarding school and ah, there’s no way she’s going to go to a state dinner wearing a jacket filled with pills.
Damien: I probably won’t tell her about that then.
Jenny: Well then maybe I will.
Damien: See if you were to do that then I’d have to tell her how you know obviously. Anyway. Don’t worry. You’ll still get your cut.
Jenny: Serena, I love your jacket. It’s so beautiful.
Damien: Yeah, actually let me help you with that.
Serena: No, it’s okay. I’m going to keep it on. It’s so pretty and it was a gift from you.
Jenny: Not that I don’t love popcorn and a movie, but I mean it’s Saturday night. I wanted to go out.
Damien: We are. In fact we have half a dozen deliveries to make at some parties.
Jenny: Again? You’re the only dealer in town?
Damien: No rest for the wicked.
Rufus: Jennifer, pack your bags or I will!
Jenny: Alright fine. I’ll do it myself.
Lily: Rufus, can we please talk about this?
Rufus: No. We can’t. You know while she’s packing her stuff maybe I’ll grab what’s left of my own.
Jenny: Okay. So let’s get it over with then. Am I grounded for life? Military school? What?
Rufus: Probably both. But this goes way past that, Jenny. See, I look at you. And I don’t see my daughter anymore.
Jenny: Go away, traitor.
Nate: Look, I’m sorry I called Rufus, but it was for your own good. You’re a really special girl, Jenny, who deserves a guy who’s gonna see that. You know? Who’s gonna be there in the morning.
Jenny: Not like you’re available.
Nate: Jenny, Damien got aggressive with Serena at the state dinner.
Jenny: Shows what you know. Damien only hit on Serena to get her to take off the opera jacket with the drugs in it.
Jenny: Damien, where are you going?
Damien: I knew you were just a kid.
Jenny: Dad, the last time I worked for Eleanor it didn’t exactly end well, remember?
Rufus: But I also remember that my daughter used to love working in fashion. C’mon, at least give it a shot. Your room’s not going anywhere.
Eleanor: My. Look who’s risen from the dead.
Jenny: I just wanted to say thank you so much for this opportunity. And I’ve really learned a lot since the last time we worked together and… I won’t let you down.
Eleanor: Well, despite our troubled past, as I told your father I’m a firm believer in second chances. I even rehired your friend.
Jenny: Agnes. Uh. Hi, how are you?
Agnes: Ninety days sober in AA.
Eleanor: Good for you. Now c’mon Jenny, what are you waiting for? Get Agnes fitted. I like to see my elves busy. Clock’s tickin’!
Agnes: What is it?
Jenny: Nothing. Ugh. Well. Truth is I was dating this guy named Damien and he was a lot of things. One of them being a dealer.
Agnes: Was he Sid to your Nancy? That’s awesome.
Jenny: You look like hell.
Chuck: Small price to pay to feel like heaven. Where’s Archibald? Don’t tell me you two finally closed the deal.
Jenny: I have no idea what you’re talking about, Chuck.
Chuck: Please. You’ve been panting at his loafers since Serena went MIA with Carter.
Jenny: So what’s step two?
Chuck: Get him drunk, take advantage of him. Do women just not get this?
Jenny: Chuck, he’s not going to go drinking with me. He made me call my dad before I slept over.
Chuck: Be here. Six o’clock sharp. And look like someone who doesn’t even have a father.
Nate: I know what this looks like.
Serena: Oh you do? Great. Well as long as you know how it looks then I guess I’m good.
Nate: It’s not what it looks like. Stop. Hey! I mean what are you even doing here?
Serena: I came to apologize for not hearing you out earlier and then I walk in to see her trying to kiss you?
Nate: Yeah, but I didn’t. Nothing happened. Same as nothing happened last night which I would have told you about if you hadn’t hung up on me.
Serena: So what about all the things she said about me. Is that really what you think?
Jenny: Yes. He does.
Serena: I’m talking to Nate, Jenny!
Nate: What? Do I wonder why you don’t trust me anymore? Yeah, I do. You won’t tell me about looking for your dad and then you leave town with Carter Baizen. And then you come back and you shut me out. What am I supposed to think?
Serena: I’m sorry. I should have told you that I was looking for my father. But I didn’t leave town with Carter. You know that. I even tried to apologize.
Nate: What are you talking about?
Serena: The night of Dorota’s wedding. I called your cell to explain everything. I even left a message with Jenny.
Jenny: What message? I never talked to her, Nate. For once, please don’t let her do this to you.
Serena: I left you a message, Nate. She said she would tell you.
Jenny: She’s lying! I never talked to her.
Nate: Just get out.
Nate: Seriously, Jenny. Just please. Leave.
Jenny: You know, you two deserve each other.
Chuck: Good thing you’re not a drug dealer anymore. That girl you sold Lily’s fake Oxy to wanted double what she paid just to give me the bottle back.
Jenny: So what’d you find out?
Chuck: My personal pharmacist is looking into it.
Jenny: Do you trust him to know if they’re bad for Lily?
Chuck: He appreciates a fine pharmaceutical. Why are you whispering? If it’s a seduction technique, don’t bother.
Jenny: Ew! You wish.
Chuck: Lily’s pills are ivermectin. They’re great at battling parasites and African River Blindness. But lymphoma, not so much.
Jenny: Well is it dangerous? I mean, does she know what she’s taking?
Chuck: What we need to find out is who prescribed them and when.
Jenny: I wish I didn’t rip the label off the bottle. I don’t remember what it said.
Chuck: The date and the drugstore were still legible. Which was enough to track down the prescribing doctor. Luckily pharmacists don’t make enough to turn down bribes.
Jenny: Okay. So what’s next?
Chuck: The mission requires an expert. Someone highly trained in the art of extorting information.
Jenny: You’re not seriously going to use this to try to get back with Blair.
Chuck: My priority is the truth. If she’s the one who can expose it—
Jenny: Then you’ll take advantage of that to make sure she doesn’t move on. Alright, I get it.
Chuck: Let’s just hope she’s willing to make herself available.
Jenny: I still don’t see why we need Blair for this. I mean don’t you read Gossip Girl? Extortion’s what I do. All day.
Chuck: This is more than headbands and high school.
Blair: The two of you here together. Please tell me there’s an explanation that doesn’t involve the Apocalypse.
Chuck: We come in peace. And with a purpose. Something’s going on with Lily’s medication. I need your mind game mastery to figure out what.
Blair: Who are you, House? I’m sure Dr. van der Woodsen knows what he’s doing.
Chuck: It’s not van der Woodsen. It’s a psychiatrist. I have an address.
Jenny: It’s weird, right? Lily so does not seem like she’s in therapy.
Blair: And you so should be. But as much as I admire the attempt to lure me back with subversive sleuthing, and appreciative as I am for your help with Columbia, the answer’s no.
Chuck: Blair, I need to find out why someone doesn’t want Lily getting better.
Blair: A heartfelt plea as well. And much more effective than a fatwa. But you obviously already know that I have a date today. And nothing you can dangle will make me miss it. Next time don’t bring Jenny Humphrey.
Blair: Pretend you’re well-bred and be polite. It’ll pay off if you ever need orthopedic surgery at Mount Sinai.
Jenny: Like when you stab me in the back.
Jenny: I don’t see what’s so wrong about wanting to see my life get back to normal.
Rufus: This is where we live. What needs to get back to normal is you.
Jenny: I didn’t know you’d be here.
Nate: I live here.
Jenny: Blair. What are you doing here?
Blair: Someone has to give you the smackdown you so richly deserve. That it’s me who gets to do it is just the cherry on top.
Blair: This isn’t copycat dressing at Constance. Or dropping dairy on your best friend to prove a point. Nate and Serena, that’s mythic. You don’t mess with that and survive. You’re hurting people I love. You’re hurting people you love.
Jenny: I wasn’t trying to, I—
Blair: Nate loves Serena, Dan loves Vanessa—god knows why—and Chuck loves me. But you Jenny? No one loves you. Except your daddy. And, after what you pulled yesterday, who knows if that’s even true anymore.
One week later…
Jenny: There’s nothing here for me anymore.
Eric: I’m here. Don’t go.
Eric: You may be a total bitch sometimes but you’re still my best friend. What am I going to do next year at school without you? Who’s going to dump yogurt on my head?