Dare Devil (Gossip Girl)

"Dare Devil" is the fifth episode of the CW television series, Gossip Girl. . The episode directed by Jamie Babbit was written by Lenn K. Rosenfeld. It aired on Tuesday, October 16, 2007 on CTV and Wednesday, October 17, 2007 on the CW.

Plot
Blair is getting ready to throw her annual sleepover. Everything seems to go perfectly until Serena bails on the event, since she has an unbreakable date with Dan. Blair isn't thrilled about Serena's desertion, but she finds a replacement, Jenny Humpgrey. Serena can't wait to find out Dan's plans about their much-anticipated date, so she seeks clues from Jenny, who, unfortunately for Serena, clams up, claiming her big brother is such a mysterious guy. It turns out Dan reserved a table at a fancy restaurant. Well, this dinner isn't exactly a triumph - while Serena doesn't seem that impressed, Dan has obviously never been at such a fancy restaurant and at last, the two of them agree to take it easy. Dan claims maybe she should see the real Dan, and they leave for Brooklyn.

Meanwhile, Blair's sleepover is definitely heating up. Blair makes Jenny realize this is anything but a sleepover. It's almost like an initiation for Jenny into Blair's "private army". Even though Jenny does realize it will be a tough game, she is eager to play. And so is Blair. "Truth or Dare" can get started. At the Ostroff Center, the doctor doesn't want to let Eric out of the treatment center, much to Lillian's relief. On the other hand, the young patient's opinion is slightly different. He needd to go out and see someone else besides his mother. Rufus calls his estranged wife Alison to let her know one her paintings finally sold. But it isn't actually Alison who answers, but a man. Actually, as he claims, a friend of Alison. Rufus is hurt, hangs up and decides it's high time he gets drunk. Blair dares Jenny to break Eric out of the Ostroff Center and she is successful. Then the sleepover girls plus Eric head to an exclusive club where a gleeful Jenny dares Blair to kiss a random guy. Undaunted, Blair doesn't hold back and, after a hot kiss with a stranger, snags the guy's cell phone and dares Jenny to fill his girlfriend in on his fiancèe's plilandering behavior. She doesn't back down, and tells "Amanda" all about the event. Meanwhile, Dan and Serena are playing pool. Actually, this is not Serena's best talent and Dan is trying to teach her. The Ostroff Center lets Lillian know that Eric is missing. Since she is positive Serena dragged her brother out of the center, Lillian tries to call her, but Serena's forgeot her cell phone in her purse, which is at home. Lillian ends up seeking help from Rufus, claiming she needs Dan's phone number. Rufus tells Lillian she's freaking out over nothing, and hangs up. But Rufus has always been such a good guy so, in the end, he can't help but call his son, who informs him that Eric is definitely not with the two of them. At the time of the phone call, they were actually about have their first kiss when Dan's phone rang. Lillian comes over to Rufus' and he fills her in on Dan's words. Rufus suggests they wait for Eric there. Lillian accepts and they cook dinner. While they're talking about the past when Rufus was a young musician and Lillian wasn't a stuck-up socialite but a more relaxed groupie, Lillian confesses to Rufus about Eric's attempted suicide.

At the same time, Dan and Serena catch up with Blair, Eric, Jenny and the other girls. Serena can't believe Blair got Eric out of the Ostroff Center without even telling her. Serena isn't the only one upset, though. Dan is quite disappointed in Jenny, as well. Eric assures Serena he just couldn't stay at the center anymore. Serena claims she will talk to their mother. Meanwhile, Jenny tells her brother to trust her, because she won't forget who she is. Dan lets her stay with Blair and her friends, however, Blair's game is not over yet. Blair hands Jenny the keys and dares her to enters Waldorf's shop and steal a jacket. Jenny goes into the shop and here comes the countdown. Five, four, three, two, one. The girls run away, the alarm goes off, and Jenny is locked in. Found at the scene of the crime, a confident Jenny tells the cops she is Blair Waldorf and she entered her mother's shop because she wanted to get her jacket. Eleanor is in Paris, right now and Jenny - or better, Blair - doesn't want to make her angry by calling at such a time. The cops want to believe her but are still unsure, until Jenny offers up her keys as proof. After Serena and Dan took Eric back to the Ostroff Center, Lillian pays him a visit. It seems he finally gets to come back home. Meanwhile, Dan and Serena finally kiss. And someone shows up at the Waldorf's. Jenny. Blair, who is definitely surprised by Jenny's unexpected success, points the only empty bed: Jenny earned it. But a newly confident Jenny declines. Blair is shocked, since nobody leaves the sleepover. Jenny tells her (not asks) that she'll see her for lunch on the steps on Monday. An astounded Blair agrees. Jenny steps into the elevator, a sly smile playing around her lips, leaving a more-than-impressed Blair behind. It's official: Blair has created a monster.

Chuck Bass and Nate Archibald did not appear in this episode.