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

With Blair's boyfriend Nate helping to close up the family yacht for the season, Blair is free to focus on the most important event of the fall: her annual sleepover. A tradition since the year 2000, each one more decadent than the last. No expense or reputation is spared. With everything from trundle beds to truffles in place, all that's missing is sleepover star and Waldorf BFF Serena van der Woodsen.

-Gossip Girl


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.



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

Memorable Quotes Edit

Gossip Girl: 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: I'm not a stop along the way; I'm a destination

Dan: It's a nice place that you and eight hundred other people have got here.

Serena: Yeah, the identical surroundings do make you crazy after a little while. Sometimes I feel like I'm in a secret government experiment.

Dan: Most government experiments don't have plasma TVs and maid services. Just something I've noticed.

Blair: As my mother always says, "Fashion knows not of comfort. All that matters is the face you show the world."

Gossip Girl: Spotlight on little J. Now put to the test by one queen bee. Will J take the bait and go from Brady to Britney? Or will her goodie too shoes mindset turn into the night's biggest buzz kill?

Blair: I have a big problem. Starts with the capital RX

Ostroff Nurse: What drugs have you been taking?

Blair: Hmmm, caffeine, nicotine, ketamine, JGP, PCP, LSD, juraida sepam? Flurazepam? All the pams really, you know, I don't discriminate.

Gossip Girl: This just in, "Truth or Dare" has gone into overtime. Looks like no one told Little J you don't beat the Waldorf's at their own game

Lily: I may hold the reins a little tight but life is complicated. Especially once you have kids. You know, when they're little you are their whole world and then one day the wall goes up and you're on one side and they're on the other.

Rufus: Well, they don't like to admit it but they want us to break through.

Cultural References Edit

  • Beyonce – When Jenny tries on a dress, Blair says “ Too Beyonce.”
  • Cinderella – Gossip Girl narrates about Serena “ Cinderella stepping onto a pumpkin instead of her carriage
  • Donatello from Teenage Mutant Ninja Turtles – Dan mentions this character and the Teenage Mutant Ninja Turtle franchise when he says “ This is the entire contents from my teenage mutant ninja turtle piggy bank, it’s time to break Donatello open.”
  • Hannah Montana – Jenny tries on an outfit and Blair says,” Too Hannah Montana”
  • Hedge Fund Mafia – Blair says,” Who let the hedge fund mafia in here? I thought Matchy Matchy was over.”
  • Hello Kitty – Gossip Girl narrates about Jenny,“ Hope that Hello Kitty sleeping bag doubles as a parachute.”
  • Mary-Kate Olsen – Jenny tries on an outfit and Blair says,“ Too Mary-Kate
  • New York Film Festival – Serena asks Jenny if this festival is still going on
  • Visconti Blair tells Isabel to take the girls to this shop

Food & Drink Edit

  • Cappuccino – Blair says sarcastically to the nurse that she'd love one
  • Chicken – At the restaurant, Dan orders chicken and says “ How about chicken? You can’t go wrong with chicken.”
  • Grapes – Blair and Jenny eat grapes once Jenny arrives at the sleepover
  • Lapin – Dan asks the waiter what Lapin is, the waiter informs him it’s rabbit and Dan says he won't be having that.
  • Lobster Bisque (Soup) – Serena orders this at the restaurant 
  • Marshmallows – Jenny says to Blair,”I once had to eat an entire bag of marshmallows.”
  • Martini – Blair offers Jenny a martini and she says she doesn't like vodka. Blair says “ This is gin, as it should be.” Jenny is then pressured into drinking.
  • Muscovy Duck – Serena also orders this at the restaurant 
  • Schnapps – Blair says to Serena “ While you get drunk on schnapps and moon the N.Y.U dorms from the limo window.”
  • Truffles – Gossip girl narrates that their will be truffles at Blair’s sleepover
  • Quail – At a restaurant, Dan asks the waiter “ How’s the braised quail?”

Gallery Edit


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