"Couture and canapé are just another Saturday night until you add a mask. But preparing for a ball is an event in itself. Which is why queens invented handmaidens." - Gossip Girl
Dan finds himself caught between two girls when his childhood friend, Vanessa, returns to Manhattan and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the masked ball, Blair sends Nate on a scavenger hunt, but Nate is distracted by his feelings for Serena. Although Blair said that outsiders were not welcome to the party, a disguised Jenny and Dan sneak into the ball. Finally, Lily asks Rufus to accompany her to an Eleanor Waldorf event hoping to make Bart Bass jealous.
Tonight's Gossip Girl begins with GG herself (voice of Kristen Bell) explaining that tonight is Blair's big masquerade ball. Rich people get tired of normal parties, you see, so they have to mix things up by putting masks on. Blair orders her handmaiden, little Jenny Humphrey, all over the city doing errands to prepare for the ball. Jenny goes to pick up dresses for Blair and her ladies-in-waiting from a dress shop. The proprietor of the shop lends Jenny a diamond bracelet to wear to the ball and charges it to Blair's account.
Blair tells Serena that she is planning a scavenger hunt for Nate at the ball. She has instructed Nate to get clues from her ladies-in-waiting, all of which lead to Blair. If he finds her before midnight, then she will cash in her v-card. Serena tries to bow out of event, considering her past indiscretion with Nate, but Blair insists that she attend and be a lady-in-waiting as well. Serena acquiesces and calls Dan to invite him to the ball. Meanwhile, in Williamsburg, Dan is stressing out that Serena hasn't asked him yet, but is soon distracted with the arrival of his best friend Vanessa (Jessica Szohr). Vanessa is his best friend, but she moved away to Woodbury, Vermont a year ago. Right before she left, he told her that he loved her, but his declaration of love wasn't well-received. Serena finally calls him to invite him, but she hears Vanessa's voice in the background asks who that is. Dan lies that it's his sister, but Serena knows this to be false because Jenny just showed up at Blair's looking for more tasks. This wigs Serena out, and stops short of asking him to the ball.
This leaves Serena dateless, so Blair orders her multicultural minions, Kati and Isabel to find Serena the hottest date ever. They set to, giving out Serena's info to all eligible bachelors in the land. Veronica Mars gets wind of Serena's solo situation, and posts a message to all the bachelors to ask her out already. Dan, who had spend an awkward day with Vanessa, sees this latest missive on the Gossip Girl site and decides to forgo his movie date with Vanessa in order to make a Seth Cohen-esque grand gesture for Serena. He rents a tux and tells Vanessa that he can't make the movie because he has to work all night on an American history paper. Vanessa is clearly disappointed, not the least because she wants Dan back.
Nate gets suspicious about Dartmouth dad, who is stressing out about impressing Eleanor at her party that night, so he enlists Chuck to help him look for evidence of shenanigans among Dartmouth dad's belongings. And he finds a bag of cocaine. Clearly upset with this, he calls Blair to ask her to talk, but she's not answering her phone. He then goes to Serena's to talk it out with her. Serena tells him not to give up trying to get through to his dad. She holds his hand as a kind gesture, but then gets awkward and quickly shoos him away.
Jenny reports to Blair with all her tasks completed. Blair commends her on a job well done, saying that it's all part of her education. It's very Sarah Michelle Gellar and Selma Blair in Cruel Intentions. Blair sees the diamond bracelet on Jenny's wrist and realizes that Jenny wants to go to the ball as well. Unfortunately for little J, Queen B doesn't allow freshmen to attend masked balls. Jenny goes home, despondent, but Vanessa tells her to go anyway, and hooks her up with a proper costume. The two sneak in to the ball through the back entrance, and just as Vanessa is about to go home to the outer boroughs where she belongs, she realizes that she has Jenny's keys and goes back into the party to find her. Uh oh! I smell trouble!
The party, by the way, is awesome. Everyone's wearing spectacular gowns and tuxedos, with bejeweled, befeathered masks.. Chuck's costume is particularly awesome. He's wearing a red tux with a horned red devil mask. Unsubtle, yet awesome. He sees Jenny from across the room. Not knowing her identity, he asks her to dance. She plays the devil herself, telling him that she'd rather go somewhere quiet to “talk.” She tells him to hide and to leave a trail of clothes for her to follow, which makes him think he has truly died and gone to heaven. He ends up on the roof, in his boxers and a wifebeater, and when Jenny finds him, she steals his clothes and runs away, leaving him locked up on the roof. Nice going, Little J!
Dan finds Serena at the party. She demands to know why he lied to her. He says he's an idiot and tells her that his relationship with Vanessa was complicated, but that now, he just wants Serena. They kiss, and of course, Vanessa is standing right there. Dan runs after Vanessa, which doesn't go over well with Serena. Dan apologizes to Vanessa, and says that he loved her, in the past tense.
Serena runs into Jenny in the ladies' lounge, and unloads her uneasiness with Vanessa's presence. Jenny reassures that although V is Dan's best friend, he's never liked anyone before the way he likes Serena. But their talk is cut short because Jenny has to leave before midnight, when everyone unmasks. The two girls decide to switch masks, and Serena lends Jenny her black, furry bolero jacket. Everyone confuses Jenny for Serena as she runs out, and this is where I have to suspend my disbelief. Yes, both girls are blond and wearing yellow dresses. But really, I think their body types, not to mention their heights, are enough to identify one girl from another. It's like how Clark Kent looks totally different than Superman, just because he's got glasses on.
Nate, confusing Jenny for Serena, tells her that he tried to get over her, but he's not, and he kisses her. She rushes off, as real Serena tells Nate to hurry up and find Blair so he can get laid. Jenny rushes past Blair, who identifies her correctly as Jenny only after see the diamond bracelet. Blair tells Nate that he was too late. All she wanted to do was start over, but he didn't even try to find her. Dan and Serena reunite, and he tells her plainly and for the record that he likes her and only her. Gossip Girl is very refreshing in this respect. Characters actually say what's on their mind, unlike on lesser shows. Serena knows he's telling the truth because he's even willing to go to the Ice Capades with her, despite having had a traumatic childhood experience at the Ice Capades.
While the young people are playing dress up, so too are the grownups. Eleanor is throwing a “Night in Tangiers”-themed party to celebrate her Bendel's deal. Lily (Kelly Rutherford) invites Rufus (Matthew Settle), who cleans up well in a suit, just to make Bart Bass jealous. Rufus gets wise to the plan and plants one on Lily, within Bart's line of sight. Bart takes a while to respond to this provocation, so until he does, Rufus opens up to Lily by showing that he may still have feelings for her. Sadly, Bart interrupts at that moment, so Rufus goes home, S.O.L. Elsewhere at the party, Eleanor decides to take up Dartmouth dad's proposal to take her company public. She also negotiates another proposal to get Nate and Blair engaged.
Nate goes home to find his parents waiting up. They found the coke and think it's his. From the look on Dartmouth dad's down-turned face, he's going to pin his coke problem on his own son.
Finally, Dan goes home to find Vanessa with a peace offering of pierogies. They apologize to each other and agree to just be each other's friends. And, I actually believe it. Again, how refreshing, Gossip Girl!
Serena: A masked ball? Dan would never want to go to something that pretentious. Where he has to wear a mask and a tux.
Blair: He likes you. He would wear a tux and a mask and one of my mother's dresses if it meant that he could go out with you.
Vanessa: Big night out with over-privileged under-parented trust fund brats from your fancy school?
Dan: Yeah, the limo is actually waiting back at the loft.
Vanessa: Good. We can egg it. Maybe slash the tires.
Chuck: So what exactly are you looking for?
Chuck: Of what? The Captain's dislike of starchy shirts? I totally sympathize. The collars chafe.
Blair: Why do you have to celebrate your Bendel's deal by turning our penthouse into an opium den?
Eleanor: Why not?
Chuck: Little Jenny Humphrey manages to get my pants off and have me not enjoy it. Quite the accomplishment.
Rufus ( to Lily): I'm sorry I kissed you, but I did it because that mercenary in the starched white shirt,he doesn't appreciate everything you have over an attractive 25 year old mannequin, because beauty fades but yours has done a remarkable job of holding on. And in the long run it's going to be his loss, and I thought he should know how it feels to lose you. Because trust me, it's not fun.
Jenny: Let's play a game.
Chuck: I'd say strip poker. But I don't have any cards.
Vanessa: You said you love me.
Dan: Loved you.In the past, in the pre-shaving sixteen-year-old kind of way. You know, things have changed.
Gossip Girl: Why is it that friends of Serena van der Woodsen have to search for her suitor? Have fables fallen so out of fashion that Princesses have to do everything themselves? Call us old school, but sometimes the Fairy Tale ending requires the Knight to get off his ass and saddle up his steed.
Blair: No more excuses! Serena must have the hottest date ever. If he's got plans, he'll change it. If he's got a girlfriend, he'll dump her. If he's out of town, he'll charter a G5 and fly home. Make it happen.
- This is the first episode to feature Anne and Vanessa as recurring characters
- This is the first episode that doesn't end with a voiceover from Gossip Girl
- Cinderella – Rufus says to Dan,”Haven't you heard? Your sister is Cinderella. Dan replies “ Let me guess, your wicked step-sister is Blair Waldorf.”
- Ice Capades – Jenny mentions that Dan was scared of the ice capades when he was 5, they are a traveling theatrical entertainment show.
- Jane Austen – Vanessa mentions this author when she says to Jenny,” Handmaiden is Jane Austen for slave.”
- Opium Den – Blair says to Eleanor that she’s turning their penthouse into an opium den. These dens were places where people could buy and smoke the addictive drug Opium in the 19th century.
- Robin – Dan says he looks like Robin from Batman
- Scarface – Chuck says a quote from this film when Nate finds his father’s drugs, “ Chichi get the llello.”
- The crying of lot 49 – Vanessa asks Dan if he still has her copy of this book
- The Pacifier – Vanessa mentions that this movie played at the Woodbury theatre for what felt like a year..
- Tux & Tales – Dan is seen on the website of this formal wear rental company
- Vin Diesel – Dan mentions this actor when he says,”They said Vin Diesel couldn’t do comedy.”
- Angelika Film Center –Vanessa offers to see a late show at Angelika with Dan, a theatre in Manhattan.
- B.A.M – Vanessa says to Jenny that her friend works at the costume department at the Brooklyn Academy of Music.
- Chapin School – Blair mentions this prestigious all girl school located in Manhattan when she sees a girl enter and says “ She’s probably a bitch from Chapin.”
- Newport – Edward says to Serena,” It’s almost enough to make you never want to summer in Newport again.” Newport is a city located in Rhode Island.
- Tangier – Lily shows Serena a dress for Eleanor’s moroccan themed party. She asks” Do you think Eleanor will find this’ Night in Tangier’s’ enough?” Tangier is a city in Morocco.
- The Limelight – Serena guesses that the drugs Nate found may be leftovers from time his dad spent at the limelight club chains in the 90’s.
- The Tunnel– Serena guesses that the drugs Nate found may be leftovers from time his dad spent at The Tunnel nightclub in the 90’s.
- Vermont – Vanessa comes to visit New York from Vermont, a state in America with a small population.
- Veselka - Vanessa offers to get pierogis at this restaurant with Dan.
- Woodbury – Vanessa lived in Woodbury, a small town in Vermont.
Food & Drink
- Canapés – Gossip girl narrates “ Couture and canapés are just another Saturday night.”
- Couscous – Lily sees appetizers and asks Eleanor if it’s couscous.
- Pierogis – When Dan says that he will make it up to Vanessa, she asks If they can have Pierogies at Veselka.
- Waffles – Vanessa says,”I’m starving and I smell waffles.”
- "Kiss, Kiss " by Yeah Yeah Yeahs
- "Guess Who " by Nekta
- "Take It To The Top " by 5 Alarm
- "A Taste (The La La Song) " by Sofia J
- "Nasty Funky Crazy " by Becca Styles
- "Ring a Ling " by Miss Eighty 6
- "Timebomb " by Beck
- "Happy Ending " by Mika
- "Secret " by The Pierces
- "Three Wishes " by The Pierces
- "Central Park " by Goodmornings