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Dare Devil

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Dare Devil
Season One, Episode 5
Air date 16 October, 2007
Written by Lenn K. Rosenfeld
Directed by Jamie Babbit
Episode Guide
Bad News Blair
The Handmaiden's Tale

Dare Devil is the 5th episode of the first season.


Dan makes elaborate plans to impress Serena on their first official date. The same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of "truth or dare." Meanwhile, when Lily discovers that Eric is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus.


Dramatis PersonaeEdit

Starring Edit

Recurring Cast Edit

Guest StarringEdit

  • Kaitlyn Benson - Maya (as Kaitlyn Ashley Benson)
  • Jed Orlemann - Club Stockbroker
  • Kim Shaw - Amanda
  • Marcella Lowery - Ostroff Nurse
  • James Lorenzo - Car Service Driver
  • David Arden Engel - Fancy Restaurant Waiter
  • Rob Falcone - Police Officer #1
  • Jaymes Hodges - Club Manager
  • Sean Ringgold - Club Security Guard
  • Peterson Townsend - Club Stockbroker's Friend

Soundtrack Edit

Quotes Edit

Gossip Girl: [voice-over] Here's an inside tip, Little J: The faster you rise, the harder you fall. Hope that Hello Kitty sleeping bag doubles as a parachute.

Blair Waldorf: [after Serena tells her she'll try to stop by the sleepover after her date with Dan] I'm not a stop along the way; I'm a destination

Dan Humphrey: If it's a real Dan Humphrey date you want, it's a real Dan Humphrey date you're gonna get

Dan Humphrey: [after seeing his little sister in a minidress at a club] The only thing causing a problem is that cocktail napkin you're wearing.

Blair Waldorf: Fashion knows not of comfort

Jenny Humphrey: So Eric's here, now it's your turn. Truth or dare?
Blair Waldorf: You have to ask?
Jenny Humphrey: I dare you to make out with that guy.
Blair Waldorf: Easy.
Jenny Humphrey: And mean it.
Blair Waldorf: Watch and learn little Humphrey.
[walks over to kiss the stockbroker guy]
Blair Waldorf: [the friend of the guy says he hopes Amanda doesn't find out]
Blair Waldorf: Who's Amanda?
Club Stockbroker: Just my girlfriend.
Blair Waldorf: Amanda never has to know does she.
Club Stockbroker: I'm not tellin' her!
[laughs with his friends]
Blair Waldorf: Look what I got.
[stole stockbroker's phone]
Blair Waldorf: I dare you to call his girlfriend, her name's Amanda.
Jenny Humphrey: Done and done.
[calls Amanda]
Jenny Humphrey: Hello? Amanda, hi this is Bl... Claire. Yeah, I just had my tongue down your boyfriend's throat and he neglected to tell me you existed until after it was over. Just thought you should know. He's a real catch! Bye.
[the girls laugh]
Blair Waldorf: Alright, sleepover of the year!

Amanda: Where is she?
Club Stockbroker: Baby, what, who, I'm here at the club with the guys.
[walks over to Blair]
Club Stockbroker: Hey! Excuse me, hello? Where's my phone?
Dan Humphrey: Hey, hey let go of her.
Club Stockbroker: Who the hell are you?
Blair Waldorf: His phone is at our table. If you weren't so drunk and drooling over every girl in this place you would've seen that.
Amanda: I'm gonna kill you!
Blair Waldorf: Oh you must be Amanda right? Well I would think twice before marrying him 'cause he's a pig.
[Amanda lunges at Blair but Serena stops her]
Serena van der Woodsen: Hey, hey, hey back off of her okay?
Blair Waldorf: I don't need you to defend me.
Jenny Humphrey: I wasn't even her who called you it was me.
Dan Humphrey: Jenny?
Amanda: So she's the one with the tongue?
Dan Humphrey: Tongue, tongue! What are you even doing here your supposed to be at a sleepover.
Amanda: You made out with a girl from a sleepover?
Dan Humphrey: You made out with him?
Club Stockbroker: I made out with her.
[looks at Blair]
Blair Waldorf: Eww. It was a dare. Amanda: A dare? What are you children? Dan Humphrey: Yeah pretty much she's 14.
[looking at Jenny]
Amanda, Club Stockbroker: 14!
[Amanda and stockbroker say in unison]
Club Stockbroker: Jesus I swear, I had no idea baby. I mean look at her, I mean she's jailbangin'.
Dan Humphrey: What, what's that?
Jenny Humphrey: Dan stay out of it okay? Your just causing more problems than your solving.
Dan Humphrey: The only thing causing a problem is the cocktail napkin your wearing.
Club Stockbroker: That's what I'm talkin' about!

Blair Waldorf: What was that I heard? Erik's coming home? It's perfect timing.
Serena van der Woodsen: How so?
Blair Waldorf: Well it gives your mother and brother time to bond alone tonight while you get drunk on schnapps and moon the NYU doors from the limo.
Serena van der Woodsen: Blair what are you talking about?
Blair Waldorf: S it's only the most important night of the fall.
Serena van der Woodsen: Oh, the sleepover.
Blair Waldorf: I prefer soiree. Sleepover is so sophomore year.
Serena van der Woodsen: Look you know I can't go to that I have that plan.
Blair Waldorf: Serena, when there's a Waldorf soiree, there's nothing else in the social calendar.
Serena van der Woodsen: Blair the plan is Dan. Remember the guy you realized who's actually a human being and worthy of your time and attention? No offense.
[in reference to Jenny's brother]
Jenny Humphrey: None taken.
Serena van der Woodsen: Look I'm really sorry but this date is unbreakable. Maybe we can swing by later or something...
Blair Waldorf: I'm not a stop along the way I'm a destination and if you refuse to attend I'm gonna have to find a replacement, girls the waiting list.
Serena van der Woodsen: Ok, um well I should get going.

Blair Waldorf: Little Jenny Humphrey, why didn't I think of you before? You have no plans your coming to the soiree.
Jenny Humphrey: Me, really? Kati Farkas, Isabel Coates: Her really?
[Kati and Isabel say in unison]
Blair Waldorf: The thing is, if you come, you'll have to be up to a little more than just sleeping.
Jenny Humphrey: I'm up for anything!
Blair Waldorf: My place. Seven o'clock sharp.
Jenny Humphrey: Okay, bye!
Blair Waldorf: Oh, a girl's first sleepover. Something she'll never forget, let's make sure of it.
Harper: Taking bets on how long she lasts.
Maya: Fifty bucks says an hour and not one minute more.

Blair Waldorf: Let's wrap this up shall we. Truth or dare? Oh, and you already used your truth.
Jenny Humphrey: So... dare?
Blair Waldorf: I dare you to jailbreak Erik.
Jenny Humphrey: Blair...
Blair Waldorf: It's perfect. You want in and he wants out. What's it gonna be? Do or die little J.
Jenny Humphrey: Let's do it.

Jenny Humphrey: Catch. [throws Blair her keys]
Blair Waldorf: Jenny? Well, well looks like you came to play afterall. You know which trundle bed is yours. Sleep tight. You've earned it.
Jenny Humphrey: Actually I'm going home but thanks for inviting me it was a blast.
Blair Waldorf: What do you mean you’re going home? Nobody ever leaves a sleepover.
Jenny Humphrey: Well I guess there's a first for everything. Oh and I'm keeping the jacket if that's okay with you. Monday lunch on the steps?
Blair Waldorf: Done and done.

Gossip Girl: [voice-over] Spotlight on little J. Now put to the test by one queenbee. Will J take the bait and go from Brady to Britney? Or will her goodie to shoes mind set turn into the night's biggest buzz kill?

Blair Waldorf: [pretending to be a drug addict while jailbreaking Eric] Okay, I have a problem, I have a big probleeem. Starts with the capital RX
Ostroff Nurse: What drugs have you been taking?
Blair Waldorf: Hmmm, caffein, nicotin, ketamin, JGP, PCP, LSD, juraidasepam? Floreaisepam? All the pams really, you know, I don't discriminate.
Ostroff Nurse: Apparently not.
[on the phone]
Ostroff Nurse: Code yellow, floor six. Why don't you wait right here? I'll get a doctor.

Trivia Edit

Although credited, Chace Crawford (Nate) and Ed Westwick (Chuck) do not appear in this episode.

Gallery Edit


Dan and Serena Dare Devil06:26

Dan and Serena Dare Devil

Gossip Girl S01E05 Dare Devil Clip01:37

Gossip Girl S01E05 Dare Devil Clip

Gossip Girl Dare Devil Preview01:14

Gossip Girl Dare Devil Preview

Gossip girl S01E05 Dare Devil HQ00:36

Gossip girl S01E05 Dare Devil HQ

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