Tonight on "Gossip Girl," everyone learned a valuable lesson: "You can't show up at a masked ball and not expect at least one social-climbing doppelganger to try and impersonate you." Also, that Lily Rhodes Van der Woodsen Bass Humphrey can't be trusted. Oh, and that you probably shouldn't take a road trip with your 10th-grade English teacher, since your innocent friendship might be misinterpreted by, well, everyone. So okay, three lessons!
In other news, we finally learned the root of Juliet's vendetta against Serena. It seems that her brother Ben taught at Knightly, the Connecticut boarding school S attended after leaving Manhattan pre-Season 1. He and Serena got close, and though she clearly had feelings for him—even propositioning him when they found themselves stranded in upstate New York after taking an ill-advised trip to Vassar together—he turned her down, since she was 16 and, oh yeah, he was her teacher. "You know, I think he was the only guy ever to say no to me," Serena tells her therapist at the Ostroff Center while recounting the incident.
Though Serena says she and Ben didn't speak again after that, the school was informed that Ben had slept with a student—and even obtained an affidavit confirming that she and her teacher had consummated their relationship. Ben was subsequently told that if he accepted a plea bargain, he could serve a five-year sentence for statutory rape and transporting a minor across state lines. That's why he's in jail now, and why he's convinced that Serena ruined his life.
The truth slowly comes out over the course of the episode, as Dan and Blair head to Connecticut on a mission to find Juliet—Gossip Girl helpfully sends them on the right track by giving them an address—and Serena gradually tells her shrink the tale of her sordid past. In CT, D and B run into Damien Dalgaard, the preppy drug dealer who went to Knightly with Serena—and who almost took Little J's virginity last season. He lets them know that he sold Juliet the pills she used on Serena and, with his help, Dan and Blair learn the secret of Ben.
As they're discovering the truth, Juliet happens upon the group of three and, panicked, heads back to the Upper East Side. She calls Ben to let him know that she's getting ready "to finish this thing once and for all, like I should have done in the first place," and he understandably flips out, since she's making it sound like she's about to take a machete to Serena's beautiful hair or something. Thankfully, Nate happens to be walking through that part of Rikers at that very moment, and Ben recognizes him. (Have the two of them ever met? Eh, whatever.) Ben tells Nate that Serena's in danger.
So Nate does the logical thing: He calls Dan and is all, "Dude, guess what I just heard." They agree to meet at the Van der Woodsen compound that evening. (Everyone gets there around the same time, even though Dan and Blair were at least two hours away—then again, it takes people on this show about two minutes to travel from the Upper East Side to Williamsburg, so what are you going to do?). Lily is, of course, having a party.
Meanwhile, Serena leaves her therapy session only to find Juliet waiting in her room. The Ostroff Center has awfully bad security. There, Crazy J comes clean about her entire scheme, calling Serena a "stupid bitch" for good measure. But when she explains that she did what she did because Serena sent Ben to prison, Serena is confused—she never signed a affidavit. And then she realizes who must have forged her name.
As Lily makes a speech to her guests about how her family has always come first, Serena suddenly shows up and lets loose on Lily. (Again: The Ostroff Center just let her leave? That is a seriously poorly-run mental health hospital.) "She wants you all to think she's the perfect host and mother and wife, but the truth is she's a selfish liar who will destroy anyone that gets in her way," she spits after telling everyone that she just got out of Ostroff.
Yes, Lily did indeed sign Serena's name and get Ben sent to jail. She claims, though, that she did it for Serena's own good: If she hadn't, Serena's horrible record would have prevented her daughter from ever attending a decent school in New York again. Serena growls that she will never "have to do anything for [Lily]" ever again after her mother's confession and stalks away. It turns out, though, that Serena isn't the only young person Lily's disappointed—Chuck also learns at this moment that she's planning to sell Bass Industries, even though she had promised to give it back to him.
We flash forward one week, where every young principal (minus Vanessa and Jenny, though who even remembers them?) has gathered for a meal at the Humphrey loft. It's the gang's last hurrah before winter break; Chuck is off to New Zealand, where he hopes to have sex on the beach and, maybe, convince Uncle Jack to help him win his company back. Serena's going on a road trip to see the judge that convicted Ben, and though she invites Dan along, he declines—he's still smarting from something Blair said to him about how he once gave everything up for S. Nate's headed to his grandfather's, though he'll be back on the UES soon enough to welcome his father home from jail.
That means Blair and Dan are the only ones left in the city. As the episode closes, they do dishes together and discover that they're both planning to attend the same screening of a French documentary. Uh-oh… this can't be leading where it seems to be leading, right?
Oh, and Serena also goes to see Ben at Rikers, where they have a tearful reunion. Will she somehow manage to spring him from the clink, using only the power of that shiny mane and her magical cleavage? What sort of corporate espionage will Chuck resort to to win back control of Bass Industries? And do the writers seriously expect us to believe that Dan and Blair could ever, ever be a couple? We won't know until January 24, when "Gossip Girl" returns.
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