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.
Dan makes elaborate plans to impress Serena on their first official date. The same night, Jenny is invited to Blair's infamous 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 lover, Rufus.
At the Waldorf's, Blair oversees the preparations for her annual sleepover. At the gallery, Dan shows Rufus that he's planning to cash out the contents of his piggy bank in order to afford to take Serena on a nice date. He asks if he wants him to deposit the check from the piece of Alison's art that sold, but realizes Rufus hasn't told her yet. Rufus explains that he wanted to go up to Hudson to surprise her in person, but Dan encourages him to just call her and see if it's even okay first. At Constance, Serena finds Jenny to see if she can get any hints about what Dan is planning for their date. Jenny advises her that Dan is a jeans and t-shirt tip of guy, so casual attire should be fine. Afterwards, Serena receives a call from Eric; who is ecstatic that Lily has agreed to let him come home for a weekend. He hopes that he'll be let out in time to see Serena before her date and they hang up. After the call, Blair tells Serena that she's glad Eric is coming home so he can bond with Lily while she goes to the sleepover. Serena reminds her that she has her date with Dan that night, and Blair has her minions consult the waiting list to fill Serena's spot. Serena leaves, and Blair decides to invite Jenny to come in her place. She warns her to come prepared for more than just sleeping and tells her to come over at seven. Jenny excitedly agrees and hurries home while the other girls take bets on how long she'll last. At Ostroff, Lily tells Eric that she and the doctor agreed that he isn't quite ready to go home yet. Disappointed, Eric accuses Lily of wanting to keep him there forever, which she denies. She tells him that they'll talk about it the next day and leaves.
At The Palace, Dan arrives to pick up Serena. When she opens the door, she discovers he's dressed in a suit and tie. Realizing her mistake at dressing in jeans, she lies that she just got in and was about to change. While he waits for her, Lily comes home and asks if Serena knows he's there. He says that she does, then notices her shopping bags. She says she had a lot on her mind then asks where he's taking Serena. He jokes that he's taking her underground, then admits he can't stop talking when he's nervous. Serena then emerges from her room, ready to go. Lily reminds her to be home by one and they leave. On the street, she spots a Vespa and excitedly tells Dan that she loves Vespa's and that she once spent a summer in Italy riding around on one. A driver then calls out to Dan and Serena realizes he didn't rent them a scooter after all. Disappointed, she gets into the car with him. At the Waldorf's, Jenny arrives to find the sleepover in full swing. Blair says she's so glad she could make it and escorts her into the living area. Meanwhile, Dan and Serena have dinner at a fancy and very expensive French restaurant. They order, and Serena excuses herself to go to the restroom to freshen up. While she's gone, Dan asks the waiter how much what she ordered was; then asks to cancel his main dish and to just have the appetizer instead when he learns how much it cost. Back at the Waldorf's, Blair has Jenny try on several outfits to find her look for the evening. They finally settle on a strapless yellow dress and Blair then hands Jenny a martini, She cautiously takes it and only sips it once she's told to either drink it or go home. Afterwards, Blair announces that it's time to play truth or dare, which Jenny is excited for; until she realizes that the dares are pretty extreme. At Rufus' gallery, he decides it's time to call Alison. He dials but hangs up when a man answers the phone. He tries again, and when the same man answers, he says he thinks he has the wrong number. The man asks who he's calling for and he says Alison Humphrey. The man tells him to wait a second, and Rufus hears him call for Al. He asks who Rufus is, and then says his name is Alex and he's a friend. Alison then comes to the phone but Rufus hangs up before saying anything to her.
Back at the restaurant, Dan asks for the check and the waiter glances awkwardly at Serena. She admits that she had the meal put on her mom's credit card and Dan gets offended, saying he can pay himself. He asks if he did something wrong, and she confesses that the date she wanted wasn't the one he thought she wanted. He tells her that if it's a real Dan Humphrey date that she wants, then that's what she's going to get. Excited, they leave the restaurant holding hands. Back at the Waldorf's, a fellow sleepover guest returns from her dare, which was to steal the doorman's uniform. Jenny's phone rings and Blair opens it to find a text from Eric, saying he's still in prison. Blair asks the other girls to head to Visconti and that she and Jenny will meet them there. They leave, and Blair tells Jenny that her dare is to bail Eric out of The Ostroff Center. She accepts the dare. At Ostroff, Jenny goes to retrieve Eric while Blair pretends to be a drug addict wanting to seek treatment to distract the receptionist. When she leaves to go get a doctor to look over Blair, they sneak Eric out. At The Palace, Lily receives a call from the center that Eric is missing. They describe the girl that left with him as young, blonde, and beautiful, and Lily assumes that it was Serena. She promises to find them and calls Serena's cell, which she finds in the suite. Meanwhile, Dan and Serena go to a pool hall. He wins $75 to pay her back for her dinner, which she accepts. He asks what they're going to do now, and she suggests that he play her. At the loft, a drunken Rufus gets a call from Lily, who lies that Eric is missing from their hotel room and she needs Dan's phone number because Serena left her phone. He replies that if Eric is with Dan and Serena on their date, they're probably having fun so she doesn't need to worry. He hangs up before she can argue. At Visconti, a drunk businessman flirts with Blair but she turns him down. She goes to the table where everyone is waiting and Jenny says it's her turn to dare Blair. She dares her to make out with that guy, which Blair does. Afterwards, a friend of his comments that he hopes Amanda doesn't find out. She asks who Amanda is and he admits she's his girlfriend. She goes back to her table, and reveals she stole his phone. She dares Jenny to call Amanda, and she does. Afterwards, they toast to sleepover of the year.
Back at the pool hall, Serena loses in pool to Dan. She reminds him that he promised to teach her how to play better if she lost, which he agrees to uphold. They play a little, and are about to kiss when Serena feels his phone vibrating. He answers it to find Rufus on the other end. When they hang up, he tells Serena that she needs to call Eric right away. At the loft, Lily arrives to ask Rufus for Dan's number in person. He admits that he realized he could have been more helpful earlier and called himself to see if they knew where Eric was. He continues that Serena was able to reach Eric and that she and Dan are going to get him. Lily becomes upset that he didn't call to tell her and Rufus invites her to sit and wait for Dan's call that they're together. She asks for something to eat, asking if he still remembers how to cook. At Visconti, Dan and Serena look from above to see if they can see Jenny or Eric. A girl comes over to Serena and demands to know if she's Claire. Serena says no and she walks away. Meanwhile, Amanda confronts the businessman and he realizes Blair stole his phone. He orders her to give it back just as Dan and Serena come over. Amanda threatens to fight Blair and Jenny says that she's the one who called, not Blair. Surprised, Dan asks what she's doing there since she's supposed to be at a sleepover and they all realize how young Jenny is. The businessman comments that Jenny is jailbait and Dan shoves him, resulting in them all getting kicked out. Eric approaches and smiles at Serena, saying he told her everything was okay. Back at the loft, Rufus and Lily cook Bolognese sauce together and she reveals to him that Eric was really missing from Ostroff, not the hotel. She explains about the suicide attempt, and that she doesn't know how to ensure that he won't try again. The phone rings and Rufus learns from Dan that they're taking Eric back to Ostroff. Lily says she should meet them there and he offers to help her pack up the food, but she decides to stay and eat quickly before she goes.
Outside the bar, Serena berates Blair for kidnapping Eric. However, Eric sides with Blair and says that getting to be outside after dark with someone who isn't Serena or Lily was worth the trouble. Serena softens, and promises Eric that they'll work on Lily. Meanwhile, Dan tells Jenny that he's taking her home. She refuses to go with him, saying that she's not going to forget who she is even though she hangs with Blair and her crowd. Dan decides to let her go with them and she runs to catch up. Serena comes over to Dan and says that they should call it a night, since she has to take Eric back to Ostroff. He offers to accompany them and she accepts. Elsewhere, Blair brings Jenny to Eleanor's store and says that her final dare is to steal the jacket off a mannequin in the window. She gives her the key and Jenny cautiously agrees to go. As she's grabbing the jacket, Blair counts to three and then runs away with the other girls when the alarm starts ringing. Jenny tries to escape but realizes the girls are gone. Back at the loft, Lily is getting ready to leave when she notices a framed photo of Rufus that she took years ago. She reminds him of his setlist that night to prove she was there and he asks why she ever gave up photography. She sarcastically remarks that social climbing was more fulfilling and the landline rings. He asks her to answer, which she does, and finds Alison on the other end. She hands Rufus the phone but when he takes it, he hears her hang up. Lily says he owes her an explanation but he replies that he doesn't owe her anything at the moment. She thanks him for being a good friend and leaves. Back at Eleanor's shop, Jenny is questioned by the police. She lies that she is Blair and that she left her jacket there on accident. The officer asks for Eleanor's number to confirm the story, but Jenny says she is in Paris. He asks for some way to confirm what she's saying is true and she shows that she has a set of keys, so he can watch her lock up. Elsewhere, Dan and Serena take a walk after dropping Eric off. They discuss Jenny and Eric, and realize that they're both good kids. They then share their first kiss on the street. At the loft, Rufus listens to his band's old records while he reminisces on the photos Lily took. At Ostroff, Lily wakes Eric up and says that they'll discuss the night the next day; after he comes home and sleeps in his own bed. She admits she doesn't know how his being home will affect them, and he says he's not worried. He gets out of bed and starts getting dressed. At the Waldorf's, Jenny arrives to find everyone in bed. Blair is surprised she made it, and tells her to take the bed next to her. However, Jenny says she's going home and asks to have lunch at school on Monday. She also asks to keep the jacket, and Blair says yes to both.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald (Credit only, as he does not appear in the episode)
- Ed Westwick as Chuck Bass (Credit only, as he does not appear in the episode)
- Taylor Momsen as Jenny Humphrey
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Connor Paolo as Eric van der Woodsen
- Zuzanna Szadkowski as Dorota Kishlovsky
- Nan Zhang as Kati Farkas
- Nicole Fiscella as Isabel Coates
- Jed Orlemann as Drunk Businessman
- Kim Shaw as Amanda
- There's a Pot a Brewin by The Little Ones
- Brandenburg Concerto No. 3 In G Major, BMV 1048: Allegro by London Philharmonic Orchestra & David Parry
- Rockstar by Prima J
- Came to Dance by Cadence Blaze
- Jezebel by Two Hours Traffic
- Whine Up by Kat DeLuna (feat. Elephant Man)
- Mama, I'm Coming Home by Ozzy Osbourne
- Get Your Party On by Zooland
- Something Like That by Tim
- Ringing In My Ears by Two Hours Traffic
Blair: Serena, when there's a Waldorf soirée, there's nothing else in the social calendar.
Blair: I am not a stop along the way, I am a destination.
Serena (on living at The Palace): Sometimes I feel like I'm living in a secret government experiment.
Dan: Most government experiments don't have plasma TVs or maid service. Just something I've noticed.
Blair: Well, as my mother says, fashion knows not of comfort, all that matters is the face you show the world.
Rufus: This better not be my wife.
Lily: Rufus, do you always answer the phone like that?!
Jenny (on the phone): Amanda? 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!
Serena (to Dan): There's something vibrating in your pocket and I really hope it's your phone.
Lily (to Rufus): So I made some calls but as it turns out, none of my people know your people, shocking but true. Either Dan Humphrey is an alias or your son is not very popular.
Jenny (to Dan): I know who Blair and those girls are. But I know who I am, and I'm not going to forget that just cause I hang out with them.
Rufus: Why did you give up photography anyway? You loved it so much.
Lily: Well, I guess I figured social climbing would be more fulfilling.
Serena (on Jenny): It's okay for her to want to be friends with the people she goes to school with.
Dan: Why? I'm not.
Serena: Uh-huh. And if you made half the effort she did, maybe we would have met a long time ago.
Serena: And so maybe you would have kissed me already.
- The episode title is based off the movie Daredevil.
- When Blair comments that Jenny's outfit is "too Hannah Montana", it may be a reference to Taylor Momsen almost being chosen to play the character Hannah over Miley Cyrus.
- This is the first time that the name Claire has been made to mask Blair's identity. The second time is in Dan's book Inside.
- This is the only episode where Eleanor's store is seen or even mentioned.