And her annual sleepover is no exception. Every year Blair brings in the finest trundle beds for her guests to slumber on as well as mani/pedi spa chairs from Bliss and racks and racks of clothes from Intermix. This is a night to go down in history. It’s survival of the fittest for the young girls on the Upper East Side. Only the strong come out alive. Blair was expecting all her friends to be there. Unfortunately, Serena already had plans; with none other than our lovable hipster, Dan Humphrey. Dan had been planning their date for the past week. He even took all the change from his Teenage Mutant Ninja Turtles piggy bank to Coinstar to cash it in (wow, can you say dorkage?). Dan wanted this date to be perfect. I mean, hello, he’s taking Serena van der Woodsen out! She’s the queen of the Upper East Side. The girl has dated guys twice Dan’s size, twice his age and two million times his net worth. Dan had to make this the best night of Serena’s life or else she would be gone forever and he’d go on being an anonymous virgin from Brooklyn. With Serena not attending the sleepover, there was an extra trundle bed that needed an occupant. Seems like little Jenny Humphrey was in the right place at the right time. Blair offered her the coveted spot and Jenny could hardly contain her excitement. OMG! Blair’s sleepover party! Jenny had heard about this magical night but never imagined she could ever actually experience it. Oh, sweet little Jenny, you have so much to learn. Blair’s party will definitely NOT just be eating Oreos, playing Dreamdate and making prank calls. Good luck, J. You’re so gonna need it.
Jenny arrived at the party carrying her sleeping bag (so embarrassing!). Blair greeted her and the games begun. First order of business: makeover! Jenny dressed like she was straight out of a Disney channel show. Blair offered her an Eleanor original to wear and a martini to sip. Jenny was happy to take the dress but hesitated drinking the martini. Blair told her if she didn’t swallow it she’d be on the first train back to Brooklyn. Jenny obliged. She didn’t get this far to turn back and go home now.
Meanwhile, Dan took Serena to a really fancy restaurant for their date. The restaurant was so expensive they didn’t even have the prices on the menu (this is normal for girls like Serena but definitely not normal for guys like Dan). Seems like both Humphreys were in way over their heads tonight. After Dan tried to get a good game of “mistress or second wife” going, Serena admitted this really wasn’t her scene. She wanted a date with Dan, not the date he thought she wanted. Relieved, Dan led Serena out of the restaurant and they were on their way to the date they were meant to go on.
Over at the sleepover, the night didn’t fully pick up until the girls played the ultimate sleepover game: truth or dare. And when these girls play truth or dare they play truth or dare. Kati and Isabel were dared to kiss each other and they did! Jenny hadn’t seen that much girl on girl action since she accidentally ordered What Girls Really Want on pay per view instead of the Amanda Bynes’ movie What a Girl Wants. There’s a huuuuge difference! Jenny was relieved when she got a text message from Eric van der Woodsen. But Blair quickly grabbed the phone out of her hand and read it. It was a picture text of Eric screaming and the message: “SOS! Still in prison!” Turns out, Eric was supposed to get released from the Ostroff Center that day but his mom thought he needed a little more time there (ugh, the kid’s been there so long he’s probably turned into Jello by now). Blair decided to take truth or dare to a whole new level and dared Jenny to break Eric out of the center. And what did our well-behaved a capella singer do? She accepted the dare and went straight from JV to Varsity.
While Jenny went into Eric’s room to rescue him, Blair distracted the nurses by pretending she was a mental patient who was hopped on god only knows what meds. When the nurse left to go get Blair immediate help, the three fled from the center. Mission accomplished. They met the rest of the sleepover guests at a club downtown. Now, it was Blair’s turn for truth or dare. Jenny dared her to make out with one of members of the Hedgefund mafia who was hanging at the club. And she had to mean it. Too easy. Blair smiled as she went over to one of the Hotshots. She grabbed him and kissed the Hotshot in front of everyone to see (love Blair’s audacity!). One of his friends said hopefully the Hotshot’s girlfriend, Amanda, would never find out about this. Blair rolled her eyes and called the guy a pig. Worst boyfriend ever. As Blair walked back to her friends, she showed them she had swiped the Hotshot’s phone. Blair handed it to Jenny and dared her to call the girlfriend, Amanda, and explain to her what exactly her wonderful boyfriend just did. Jenny accepted the challenge and dialed. She told Amanda her name was Bl…Claire and she just had her tongue down her boyfriend’s throat. Just thought she should know.
Over at a dive bar, Dan and Serena were having the best date ever. Never thought we’d see Serena van der Woodsen in a bar that served peanuts and prided itself on having PBR on tap. Oh, how times change. Dan and Serena played pool and picked songs out on the jukebox (Serena paid since Dan had cashed in all his quarters). It seemed like everything was going well. They even got really close to one another and it looked like they were going in to, ahhhh, kiss when suddenly Dan’s cell phone started vibrating in his pants. Or what I hope was his cell phone. Dan answered the call and it was his dad, Rufus. What a mood killer. Rufus told Dan that Serena left her phone at the Palace and her mother was furiously looking to get a hold of her. Eric had disappeared from the Ostroff Center. Serena became worried and had to find out where her brother had gone. Guess you’ll have to wait just a little longer for that kiss, Dan. Hope you’re not too blue down there.
The girls were having an awesome time dancing in the club. Even Eric was enjoying himself. Everything was going great. That is until Amanda, the Hotshot’s girlfriend, showed up. And boy was she irate. As Amanda and the Hotshot approached the girls, Dan and Serena showed up. They tried to intervene, but Amanda looked like she was going to rip Blair’s head off. Jenny stepped up and admitted she had actually called Amanda. Dan was shocked to see his sister was not only stooping to dumb teenage girl games at a club but also dressed like that! In public! Amanda and the Hotshot were livid. Who were they dealing with here? Children? Dan told them they actually are only children. Jenny is fourteen! The Hotshot called Jenny jailbait and that really put Dan over the edge. As Dan lunged at the Hotshot, the Hotshot shoved Dan into a bouncer. The kids were kicked out of the club. The game was over.
Serena was furious that not only did her little brother escape from the rehab center but her best friend helped him! Blair apologized and said she was just trying to make it up to him after the whole rehab outing at the Ivy Week Mixer. Eric told Serena he left on his own freewill. All he wanted was to get out; be with people besides doctors, nurses, and their mom. Serena couldn’t argue with that. Dan was upset too. Jenny was too smart and too nice to get mixed up in charades like this. Jenny pleaded she knows who she is and isn’t going to change for these girls. She’ll never forget where she came from. Dan softened and let Jenny go back with Blair and the girls. Dan offered to walk Serena and Eric back to the Ostroff Center. I’m sure Dan didn’t expect to be ending the night with Serena’s little brother in tow. But of course, tonight didn’t turn out to be exactly what he had planned.
On their way back to the Upper East Side, Blair told Jenny there was just one more thing she had to pull off: go into Eleanor Waldorf’s boutique and steal a jacket. It was the last thing she had to do to prove she had what it takes to hang with the elite. Blair handed Jenny the keys and watched as she entered the store. As Jenny started to take the jacket off the mannequin, Blair began to countdown. 5, 4, 3, 2, 1. RING. RING. The alarms went off and Blair and the girls fled, leaving Jenny trapped in the store with nowhere to hide. Busted. But you can never discount Jenny Humphrey. The girl is smarter than she leads on. When the cops showed up, Jenny told them she was Blair Waldorf and was just getting a coat she left behind in her mother’s store. Her mother would be so disappointed in her if she knew she had forgotten it in there. Eleanor hates absent mindedness. Jenny said she had her own set of keys so the cop could watch her close up the boutique himself. When Jenny showed up back at the Waldorf penthouse wearing the jacket and not in handcuffs or an orange jumpsuit, Blair was in utter shock. Well played, little J. Jenny threw the keys over to Blair, told her she was taking the jacket and was heading back home to Brooklyn. She will see Blair on Monday on the steps of the Met for lunch. Blair nodded. Too impressed for words.
And finally it happened. Something we were waiting for quite some time. Serena and Dan kissed. The couple (omg can we call them that now??) shared a very romantic first kiss in the middle of a New York City street. And it was actually pretty hot (maybe I need to find a guy from Brooklyn…wait, what am I saying, no Gossip Girl, bad thoughts!) Dan and Serena had sexual chemistry, which has been heating up for weeks now. Sure, this isn’t the first time Serena van der Woodsen was seen kissing someone on the street. But this time she’s definitely going to remember it. It looked like she was actually enjoying it too. It’s crazy how things turn out. One year ago Serena was running wild; dancing on bars and making boys cry. And now it seems like her focus is on just one guy. Serena van der Woodsen: monogamous?? And Dan Humphrey? One year ago this kid had never even talked to a girl, let alone kissed one on a crowded street in front of hundreds of passerbyers. Just goes to show you that miracles can happen, especially in the greatest city in the world. All you need is love.
