Gossip Girl: Bibbidi Bobbidi Boo

This week on Gossip Girl, a ghost from Dan’s past reappears, Jenny continues to be awesome, and Nate continues to suck at life.

Wait, what is Ana-Lucia doing on Gossip Girl?

A masked ball is this week’s main event, and we open with Jenny running errands for Blair. Evidently that power play last week only secured her the head personal assistant spot. The shopkeeper takes pity on our poor belabored Jenny, and loans her a gold bracelet. She’ll get to wear it at the ball as long as she returns it afterwards. She’s definitely going to lose that thing. Maybe my hopes of Jenny in juvie aren’t yet squashed.

Blair and Serena are lounging around in bed together (?) discussing the upcoming ball. Blair reveals that she’s set up a scavenger hunt for Nate – girls will give him a series of clues and if he identifies Blair before midnight, he’ll win the prize of finally getting to sleep with her. Seeing as though Blair will be the one standing around with the KY and the dildo, I think even Nate will be able to figure this one out. Serena is a little squicked out talking to Blair about having sex with Nate because, you know, Serena actually has had sex with Nate. Awk-ward! Serena volunteers to skip the party, but Blair insists that Serena not only attend, but be the one to give Nate his last clue. Blair says the ball is about starting over, and that she trusts both Serena and Nate. Good plan. What could possibly go wrong?

He likes it when you do this with your hand…

Blair asks Serena if Dan’s coming, and we learn that Serena in fact has not invited Dan yet. Meanwhile, Dan is at home with Rufus and Jenny, trying to pretend that he doesn’t care about the snub. Jenny exposits that the reason she’s Blair’s bitch for the day is to trade self respect for an invitation to the ball and a dress to wear. Guess calligraphy just didn’t cut it this time. BTW, Dan and Serena really must be soul mates because they always talk about the same exact thing at the same exact time. It’s uncanny. Serena defends herself by claiming that Dan wouldn’t want to go to something that pretentious, and Blair insists that she call Dan up immediately since the ball is that night. We cut back to Dan, whose cell phone is ringing. But wait – it’s not Serena, it’s Vanessa! Who? No fucking idea. Vanessa asks Dan if he still has some old book, and he complains that he hasn’t heard from her in a year and now she’s making him play fetch. He walks into his bedroom and it turns out Vanessa’s in there waiting for him by an open window. I think she’s another one of those Dawson’s River kids Kat and Bianca’s dad was so worried about.

Joey Potter gone ghetto

Vanessa announces that she’s going to finish high school in the city. Dan is… not really too thrilled. As he awkwardly makes chit chat, his cell phone goes off again and this time it is Serena. Vanessa scampers away to catch up with Rufus, and Dan picks up. Goaded by Blair, Serena is about to ask Dan to the ball when she hears Vanessa babbling about waffles in the background. Dan claims it was Jenny, but just as he says that, Jenny walks into Blair’s bedroom. Ruh-roh. I just want to note it was really generous of Blair to loan Jenny the Waldorf family jet. I mean, how the hell else did Jenny get from Brooklyn to the UES in approximately 2 minutes?

Jenny picks up a new list of chores from Blair and almost falls on her face running back out the door. Devastated, Serena watches the gangly legs of Dan’s lie take off, and she quickly gets off the phone without inviting Dan to the ball. She then announces to Blair that she needs a date. Blair’s already regretting that “I trust you” speech I bet.

At Nate’s, Cappy McDouche is totally stressed out about securing Blair’s mother’s account. Cappy snaps at Nate’s mom (who, incidentally, looks crazy similar to Lily) and runs out the door. Looks like someone may be having money troubles. My, my coke habits are expensive, aren’t they?

Dan and Vanessa are strolling down the street as Vanessa suggests things for them to do that night, since Dan doesn’t have any plans. Distracted, Dan doesn’t really respond until Vanessa asks if it’s weird that she’s back. She alludes to something Dan said to her (I love you?) the night before she left, and Dan points out it’s been a year and he’s not really into her whole tacky gold hoop earrings and nylon warm-up jacket look anymore. He’s an eating-disorder and Daddy issues kind of guy now. But Vanessa teases him until he relaxes and is himself.

Meanwhile, Nate is pawing through Cappy’s things looking for “evidence” while Upchuck considers which mask he should try to rape someone in tonight. They discuss the money missing from Nate’s bank account, and we find out that Cappy claimed he was just moving accounts around, and it was all back the next day. Okay, I was just kidding about the coke thing (I recap as I watch), but as Nate thumbs through some book, a little packet of white powder drops out. Looks like we really do have a drug problem! You knew it was never a matter of “if” but rather a matter of “who.” Oh, Cappy. I don’t think that’s what a real Dartmouth man would do, do you?

Nathaniel, does this scream homicidal maniac enough to you, or do I need something more?

Upchuck disappears to go pick up some roofies, duct tape, and strong rope, and a distraught Nate tries to give Blair a call. He gets her voicemail, which informs him that she’s not answering because she’s getting ready for the masked ball. I’m so glad to see that someone else regularly updates their voicemails! Every time I get up to use the bathroom I change my voicemail to make sure any caller knows I’m on the crapper. Information makes the world go round, y’all. Nate’s message just says he needs to talk to her ASAP.

Jenny has flown back in to report to Blair again, and this time Blair notices the bracelet Jenny got from that one storekeeper. After a flash of jealousy, Blair sweetly asks if Jenny really expected to receive an invitation, and then condescendingly says that tradition dictates that freshmen don’t get to go to the ball. Jenny begs her evil stepsister to reconsider, but Blair merely pats her on the head and tells Jenny that her time will come. Jenny rolls her eyes and starts wondering if she knows any rodents with sewing skills.

At the Palace, Serena admits to Lily that Dan is screwing around with someone who is definitely not his sister. Lily tells her daughter that she’s relieved, since Serena should be playing the field and acting like a dirty whore at this age. Great advice, Mom! Lily’s evening plans consist of a Middle Eastern-themed party of Eleanor’s, so she takes off to find a goat (for realz) before she heads over.

Once alone, Serena gets an IM from a random guy. Turns out Blair had put a notice out on Gossip Girl that Serena needed a date for the ball. Serena runs a Myspace check on the random, and finds out his name is Eddie, and as much as he says he wants to meet Lindsay Lohan, he doesn’t know how to spell her name. But Serena decides that Eddie’s better than going stag, and begins chatting with him. Meanwhile, Dan also sees the notice on Gossip Girl, and decides to run out and surprise Serena by showing up at the ball in a tux. So much for Vanessa.

Nate has arrived at Serena’s door, and Serena conveniently is in dishabille. She lets him in, and tries to comfort him by saying maybe the coke is left over from some last great binge in the 90s. Nate is convinced the coke is recent, and connected to money problems. Nate wishes his daddy would open up and share with him, and Serena advises that Nate try to talk to Cappy about it. Who else thinks confronting the strung-out cokehead might be a bad idea? Serena puts her hand on Nate’s arm, and he immediately gets pervy and she pulls away and kicks him out.

I’m going to need to see the cash upfront.

In the ghetto, Vanessa arrives at the Humphreys looking very ghetto-fabulous in a silver hooded jacket and bird’s-nest hair. Dan isn’t there, and Rufus takes the opportunity to let her know that she broke Dan’s heart. Vanessa says that she missed Dan and blah blah blah. Rufus takes off to meet a date (obviously Lily), and Dan calls Vanessa moments later. He lies (that’s getting to be a bad habit, Daniel) that he has a paper due and can’t hang out, as he runs down the street with a garment bag.

Sure enough, Rufus and Lily arrive together at Eleanor’s opium den. Lily plays it off like she’s doing Rufus a favor by allowing him to mingle with rich potential customers for the ugly art in his gallery. But her eyes linger on her secret lover, Upchuck Senior, so it looks like Rufus may be actually serving as an air bag for this party. Upchuck Senior comes over and introduces his young plaything, CariDee English. Lily refuses to shake CariDee’s hand, and Cari only gets 1 line and an awkward eye roll before Upchuck Senior pulls her away. Umm, great seeing you Cari! Glad to see that whole ANTM thing is working out so well. That was pointless stunt casting, but for the record, Melrose would have nailed that part. Yes, I’m still bitter. Poor but not stupid, Rufus puts two and two together and calls Lily out for using him to try to make Upchuck Senior jealous.

Would you really buy designer clothes from a woman that dresses like this?

Speaking of using people, Vanessa tells Jenny that Blair was just using her as her slave, since she couldn’t use the minions without getting the ACLU on her ass. Jenny half-heartedly defends Blair, but Vanessa is having none of it and tells Jenny that dreams can come true and Cinderella shall go to the ball! As her fairy godmother, Vanessa says she can get Jenny a dress from a costume-designer friend, and since it’s a masked ball, Blair never has to know the difference.

Arriving at the ball, Dan runs into a drunk kid, steals his mask, and enters the party by telling the bouncer the drunk kid’s name. Almost immediately, he sees Serena dancing with Eddie. Dan’s not happy. Meanwhile, Vanessa sneaks a gowned and masked Jenny through a back entrance. As she uncertainly wanders off, Vanessa realizes that she has Jenny’s house keys and enters the party herself to follow Jenny.

Blair’s standing around, pissed off as always. This time she’s mad that Nate’s not trying to figure out her scavenger hunt, and she feels like a whore just standing there with the lube and phallic devises. Blair tries to convince Upchuck to give Nate a kick in the rear, but Upchuck’s rape radar has located Jenny and he’s going to make sure that rope and duct tape go to good use. Only he doesn’t realize it’s Jenny because demi-masks evidently make it impossible to recognize anyone. He approaches Jenny and tries to pick her up, but she smoothly suggests that they skip all that and go outside to “talk.” He volunteers to get the champagne and roofies, and she tells him to meet her in 5 minutes. Man, I hope she has a plan and a taser under that dress.

That mask is so good, it could be Oprah under there from what I can tell.

Back at the opium den, Cappy is desperately begging Eleanor to let him take her company public, while she reasonably points out that he’s never handled fashion before. Nate’s mom tries to change the subject by showing Eleanor a massive heirloom diamond ring that she hopes Nate will give to Blair when he proposes. Cappy eyes the ring hungrily. That could buy him like 6 days of nose candy. That thing’s so going to be up on eBay by the end of the night. Across the room, Lily doing some hungry staring of her own, but at Upchuck Senior instead. Rufus points out that if Lily really wants to make Upchuck Senior jealous, staring at him like a kicked puppy isn’t really going to do the trick. Rufus grabs Lily and kisses her as the romantic music swells and Upchuck Senior glares. As they part, Lily is flustered but Rufus merely tells her to give Upchuck Senior ten minutes before he marches over to pee on her and mark his territory.

We’re putting this up right after our auction of Jesus’s image in 2-month-old milk curdles ends.

So shockingly, Eddie’s a complete idiot and Serena is bored to tears as they dance. As she is about to make an excuse and leave, Dan cuts in. He tells Serena he’s there to save her and she pissily informs him that she doesn’t need saving. They squabble as Nate watches forlornly from the sidelines. The minions approach to give him a clue for the scavenger hunt, but all he hears is that he’s supposed to go find Serena.

So tell us, Phantom: Who makes a better Marie Antoinette?

Jenny evidently learned a little something about tricks and manipulation last week, for when Upchuck returns she proposes a game of hide and seek. He asks how she’ll be able to find him, and she suggests that he leave her a trial of his clothes. She tries to hide her revulsion as he readily agrees. I love any plan that leaves Upchuck alone and shivering in his boxers, so game on.

Meanwhile, Dan and Serena are still squabbling like an old married couple. She asks what he’s doing there, and he exasperatedly says he ran across town and stole a mask from a drunk kid to get in the party, only to look like Robin. Which he actually does. But less gay. Serena finally calls him out on lying about his sister on the phone. He explains the situation, she admits that she wanted to invite him to the ball, and they kiss. But – and I know you never saw this one coming – Vanessa is right there to witness the smooch. Vanessa starts walking away, Dan chases her, and then the two of them bicker. I’m not really a Serena fan, but Vanessa has no grounds to be bitchy here. Maybe Dan shouldn’t have lied about writing a paper, but when you pop back into town unannounced after a year and expect your cute, young ex to be instantly available, you’re fucking stupid. Vanessa angrily reminds Dan that he said he loved her (I knew it!), and he agrees he said that but then stresses the past tense, and tells her things have changed. She gestures to Serena, hovering uncomfortably behind Dan, and says that it looks like Dan traded up. Mmm… kinda. Vanessa successfully leaves this time, and Serena disgustedly calls Vanessa beautiful, in that why-couldn’t-she-have-been-a-chunky-uggo voice. Dan runs off after Vanessa again. Moron.

Upchuck’s hanging out on the roof in his boxers and a wife-beater, rope in hand and duct tape clenched in his teeth, waiting for Jenny to find him. She opens the door to the roof and picks up his pants, while Upchuck hides around a pillar a few yards away. Oblivious to what’s about to happen, Upchuck doesn’t move and Jenny tells him she hopes he doesn’t get too cold as she slams the door, locking him out. His phone’s in his pants, so he can’t call for help. It’s awesome.

At Eleanor’s, Lily is hanging out by herself, getting some alone time, when Rufus approaches and commiserates that things are a little awkward now that they kissed. Lily corrects him and says she feels nauseated, not nostalgic. Ouch. They chat for a few minutes and just as they’re about to really kiss, Upchuck Senior strolls over with a full bladder and a leg raised in preparation. Rufus grabs the next elevator (Blair has an elevator in her home??) and goes home. Poor baby.

So let me get this straight – you like me, your son likes my daughter, and your daughter likes my son? You’re right, that IS kinda gross…

While Nate stares at her from across the room, Serena goes into the bathroom, where she finds Jenny tossing out Upchuck’s clothes. Now that Jenny’s demi-mask is off, Serena instantly recognizes her, and spills about the Dan drama. Jenny tries to cheer Serena up, but Serena’s determined to remain down in the dumps. Maybe she finally caught a glimpse of herself in the mirror – home girl is looking a little busted tonight. From some angles she looks good, but from others… It’s like that optical illusion:

Can you see both Serenas?

Jenny finally convinces Serena to stop looking like a hag and go over Dan. As she’s leaving, Serena complains that her mask is falling off, and then asks Jenny if she wants to trade. Jenny inexplicably agrees to take Serena’s shitty mask, and Serena turns over her black shrug as well because it’s too hot inside and it’ll probably be cold outside. This makes no sense since Serena is about to go outside after Dan. Plot holes? What plot holes? Jenny, who is wearing a yellow dress very similar to Serena’s, takes the mask and shrug and pulls down her hair to match Serena’s loose style. Why, again I don’t know. I don’t see this ending well, since now Jenny will look exactly like Serena and Nate seems determined to have sex with Serena in another public forum tonight.

Sure enough, the second Jenny steps out of the bathroom, Nate comes up from behind and grabs her. Instructing “Serena” not to say anything, Nate says that he thinks it may be best to come clean with Blair because he thought he was over Serena but he’s not and he can’t fight it anymore. He tries to kiss “Serena”, and after a brief hesitation Jenny pushes him and frantically runs away. The real Serena, having just missed the embrace, comes up seconds later to yell at Nate to go find Blair before midnight.

Okay, back to clubbing us over the head with the Cinderella allusions. Jenny’s running through the party, trying to escape before midnight, when everyone will take off their masks and reveal themselves. Blair sees “Serena” and grabs her arm to stop her, but Jenny plows on, leaving only a glass slipper. Or a bracelet. Whatevs. Blair instantly recognizes the bracelet and fumes that Jenny was there, just as the clock hits the witching hour. Everyone removes their masks and Blair turns to see Nate standing stupidly behind her, a minute too late. Dan also runs into “Serena” and tries to convince her to stop so he can apologize. Jenny runs right by him as well, leaving Dan surely to think that the real Serena is still pissed at him. And least he didn’t try to kiss her again.

The party over, Blair, Nate and Upchuck are on the street. Upchuck can’t believe that Jenny managed to get his pants off without him enjoying it, and Blair says Upchuck should consider himself lucky that someone else came on the roof to do some canoodling. Maybe it’s just me, but a cold gravel roof in October does not equal sexy time in my book. Blair also says she doesn’t want to know how Upchuck got the tux he’s now wearing. I’m willing to guess it had something to do with making a man out of some unsuspecting underclassman. Anyway, Nate tries to go home with Blair, and she refuses, saying that she’s been trying to plan these things so they can start over and he won’t even try. Good for her, but seriously Blair, just break up with this little bitch already. Upchuck is such a better match for her, psychotic rapist tendencies aside. He actually challenges her and keeps her on her toes. And I don’t think Blair would mind the occasional bondage. Meanwhile, Dan finds the real Serena outside and they clear up any misunderstandings again. They’re starting to really bore me. Oh, and the minions go home with Serena’s date, Eddie. Glad to see Myspace continues to get people laid.

Whoa. What a difference some hair gel makes.

Nate arrives home, and dramatically enters a study. I totally expect to see Cappy with a pistol in his mouth, but instead Nate finds both his parents sitting quietly. Boo, maybe next week. His mom says that Eleanor decided to let Cappy take her company public, but when Nate congratulates them, his mom reveals that she found the cocaine while looking for a wine opener. Cappy won’t make eye contact, and Nate’s mom begins blaming Nate for the drugs while Nate huffs and puffs in disbelief. Who thinks Nate will tell her the truth, that the drugs are his father’s? Yeah, me neither. Pussy.

If she finds the cut up straws in my pockets, I’ll say they’re from juice boxes. Yeah, that’ll work. Juice boxes. Heh. Good thinking, Captain. Go Dartmouth!

Dan’s also now back at home, and he makes small talk with Cinderella about how she missed quite the ball. Jenny smirks at him for a few moments, then gestures to Vanessa who’s waiting for Dan in his room. They chat and make up, with Dan saying he’s glad that he finally has a friend again. Yeah, until you wake up with her straddling you. We’ll see how long this platonic thing lasts.

Well guys, the previews for the next episode look pretty awesome, but with Halloween this week, the next new episode’s not until November 7th. To tide us over, leave your thoughts below: What do you think of Vanessa? Will Jenny spill the dirt she learned as “Serena”? And will Nate man up and out Cappy?