- [first lines]
- Gossip Girl: [voice-over] From the day he brings his newborn girl home, a father lives in fear... that someday she'll get hurt.
- Rufus Humphrey: How about some breakfast?
- Jenny Humphrey: [petulant] Waffles. Shocker. No, I'm good, thanks, I'll eat at school.
- Rufus Humphrey: I'll see you at 4:15. On the dot.
- Jenny Humphrey: School, home, school, home. I get it. Thanks.
- [walks away in a huff]
- Gossip Girl: That someday she'll hate him.
- Jenny Humphrey: [alone, while song plays about being devil-may-care rockstar, on phone:] Hi. I need a car. Yes, from DUMBO to the Smyth hotel. Okay, thanks, bye.
- [rearranges hair in slightly dishevelled style while song goes "All I need is a black guitar"]
- Gossip Girl: And worst of all, someday she'll grow up.
- Serena van der Woodsen: Who needs coffee after a wakeup like that?
- Nate Archibald: [her cellphone chimes] Ugh. Who's texting this early?
- Serena van der Woodsen: Rufus. He's freaking out. He can't find Jenny. He thinks she's with Damian. This is not good.
- Nate Archibald: Who, Prince Damian from the State Dinner? I thought you thought he was dreamy.
- Serena van der Woodsen: Well, that was before he tried to kiss me. After I told him not to.
- Nate Archibald: Uhm, what? And now that creep's with Jenny.
- Serena van der Woodsen: Yeah, you know what's most attractive about a bad boy?
- Nate Archibald: No, I really don't.
- Serena van der Woodsen: Your parents refusing to let you see him. Rufus is driving Jenny right into Damian's creepy arms.
- [sits up, exhales]
- Serena van der Woodsen: I'm not gonna let that happen.
- Jenny Humphrey: [things are getting a bit heavy] Oh, uhm... it's 9:30. I have Latin.
- Damian Daalgard: [impatiently] It's a dead language. It's not going anywhere.
- [hand in his hair]
- Damian Daalgard: Why don't you just ditch it and stay here with me?
- Jenny Humphrey: I can't. I have a quiz.
- Damian Daalgard: [scoffs] Come on, Jenny. Don't you think it's a little coincidental, the last time we got to this spot... in the place right underneath your kilt... that you had to go dissect a fetal pig?
- Jenny Humphrey: I did.
- [chuckles]
- Jenny Humphrey: Come on, Damian, you know I wanna be here.
- Damian Daalgard: Jenny.
- [sighs]
- Damian Daalgard: Why don't we just talk about it?
- Jenny Humphrey: What's there to talk about?
- Damian Daalgard: I think you're an amazing girl. I love spending time with you, but... when I date someone, sex is usually part of the equation. And if you're not cool with that, it's fine. But say something. You can't just shut me down every time we're alone together.
- Jenny Humphrey: I'm not. I... It's just not a good day. I mean, I have a quiz, and then I have that other class.
- Damian Daalgard: You're younger than me. I get it. Could it be that you've never...?
- Jenny Humphrey: [with nervous laughter in her voice] No, Damian. It's not like that.
- [sits down next to him on the bed]
- Jenny Humphrey: Look, I just don't like the first time with someone to be rushed.
- [shakes her head]
- Jenny Humphrey: And I have school.
- Damian Daalgard: Okay. Well, how about tonight? After your father goes to sleep, you can sneak out. No rush. Okay?
- [his hand caresses her cheek]
- Damian Daalgard: Nice and slow.
- [brushes hair away from her eyes]
- Jenny Humphrey: Yeah, perfect. Um... it's on, Dalgaard. I will see you tonight.
- [he kisses her]
- Gossip Girl: [voice-over] There's always a moment a father can't let himself fear: the day his little J decides to lose her big V.
- Lily van der Woodsen: She's a teenage girl. Cutting school to be with her boyfriend isn't exactly criminal behavior.
- Rufus Humphrey: I guess I'm still holding out hope that somewhere underneath that... mop of blonde hair is my little girl.
- Rufus Humphrey: You're gonna dream of the days you were just grounded. From now on I will escort you to and from school. Queller will assign someone to walk you from class to class, and you will have lunch in her office.
- Jenny Humphrey: [chuckles] Dad, I ditched class to be with my boyfriend. So what? It's not like it's affecting my grades. You can't keep treating me like a child!
- Nate Archibald: [on phone to Blair] Whoa, I'm not gonna apologize. I did the right thing, okay? Serena may not get it, but losing her virginity is a huge deal to a girl like Jenny.
- [Blair knows there's gonna be trouble]
- Serena van der Woodsen: Oh, and it wasn't for me? Why is that, Nate? Because I was a huge slut when I was Jenny's age?
- Nate Archibald: Look, I didn't realize I was on speaker phone, okay? I didn't mean to say...
- Serena van der Woodsen: That's exactly what you meant.
- [ends call]
- Blair Waldorf: [re the protesters outside] Pathetic! Suburban moralists in mom jeans. I'd pity them if I wasn't afraid they'd spill orange soda on my Christian Louboutins.
- Jenny Humphrey: [while Nate is searching for her at the wrong hotel] Right under their noses. Booking a room at the Empire was genius.
- Damian Daalgard: [closing in] Are you sure you wanna do this?
- Jenny Humphrey: Yeah.
- Jenny Humphrey: [in bed together] Damian... there's something you should know before...
- Damian Daalgard: Yeah? What is it? You can tell me anything.
- Jenny Humphrey: [lowers her eyes] I'm a virgin.
- [he smiles]
- Jenny Humphrey: I just wanted you to know in case...
- [shakes her head]
- Jenny Humphrey: I don't know. I just wanted you to know.
- [big eyes]
- Damian Daalgard: I kind of figured. It's really not a big deal.
- [moves closer]
- Jenny Humphrey: [evasive] Well, actually, I mean, it is kind of a big deal for me. I mean, I chose you,
- [shakes her head]
- Jenny Humphrey: and that... It means something to me. Does it...?
- Damian Daalgard: Jenny, why don't we talk about this after?
- [she looks uncertain]
- Damian Daalgard: Okay?
- Jenny Humphrey: No, I... I don't wanna do this.
- [shakes her head, and he scoffs]
- Damian Daalgard: [gets up out of bed] Uh...
- [gets dressed]
- Jenny Humphrey: [dismayed] Damian, where...
- [exhales]
- Jenny Humphrey: where are you going?
- Damian Daalgard: [heads for the door] I knew you were just a kid.
- [sighs as he leaves the room, and she sniffles]