The Wrath of Con is the 23rd episode of the second season and the 41st overall.
Four wise men once said "I get by with a little hope from my friends." But on the Upper East Side, there's the added challenge of finding out who those friends really are.
Blair pressures Georgina into making amends for her past bad behavior by helping in a scheme. The rivalry between Nate and Chuck over Blair comes to a head. Meanwhile, Lily hatches a secret plan to help Rufus with Dan's college tuition.
Chuck and Georgina are riding back to Manhattan from the Christian camp when he receives a call from Serena. She informs him that Gabriel left town with all the money Lily, the co-op members, and Poppy invested with; making the whole thing a scam. Chuck asks how much he got and Serena says she doesn't know, but she's going home to tell Lily. She apologizes again for not believing him and Blair and they make plans to talk later. At the VDW's, Serena arrives home and is greeted by Lily, who muses about how wonderful Gabriel is. Before Serena can explain anything, Lily gifts her with a bracelet that belonged to her great grandmother. She says she took it out of the safety deposit box earlier that day and she wants her to have it to represent what an amazing woman she's becoming. Her phone then rings and she answers it while Serena says they can talk later. As she walks away, she calls Blair saying she needs her help. At Nate's new apartment, Blair tries to flee but Nate tells her that she can't use Serena as an excuse anymore to avoid talking. He asks her again if she will live in the apartment with him but she doesn't answer and leaves, with him following. Elsewhere, Rufus is obscenely happy and Dan and Jenny are concerned with it. Rufus excitedly reveals that Gabriel let him in on a great investment and that he's going to propose to Lily. Both kids are shocked and he says that he just has to receive Eric's approval first and then he's going to do it.
At the VDW's, Serena fills Blair and Nate in on Gabriel's scam. Blair asks if she's okay and Serena says she doesn't know, as she's trying to figure out what was real and what wasn't. She then says that she has a plan and she wants to know if they think it's crazy. Meanwhile, Chuck arrives in the apartment with Georgina. She wonders where Blair is, saying she just wants to apologize to her. He tells her to wait in the kitchen while he goes to see what's going on. In Serena's room, she calls Gabriel and leaves him a message saying she thinks she might be pregnant. Chuck asks if they called the police but Serena says no, because Lily would find out for sure and she wants to handle it on her own. Nate adds that they're taking care of it fine without him and Blair advises Serena to let Chuck fix it. Dan then enters the room and asks what missing money they're talking about. Blair fills Dan in and he shockingly says that Rufus invested his college money with him. Serena asks him not to, saying she'll take care of it. Blair scoffs that her plan will only work with an act of God; and Georgina enters the room. They all begin to yell at each other until Georgina holds up Serena's ringing phone, asking if anyone knows a Gabriel. Serena grabs it and answers. Later, she goes to The Palace to meet with Gabriel alone. She sits down and he's relieved that that's what she was scared about; being pregnant. She then says that she's not but she knows he scammed everyone; and he can stay safe so long as he returns the money. He says he can't give the money back and Chuck comes to the table, followed by two security details. He tells Gabriel that he won't be leaving his hotel until he returns the money and if he doesn't, he'll call the feds. Nervous, Gabriel says that he would give the money back if he could but he can't because Poppy has it. Meanwhile, Dan finds Lily and tells her about Gabriel's scam, as well as Serena thinking she can get it back herself. Lily is shocked, but instructs Dan not to tell Rufus because she's going to take care of the problem. She asks him not to say anything to anyone and then hugs him. Back at The Palace, Gabriel explains that Poppy scams people for money in order to help her build a life of luxury and status. They met at a Mercedes launch party and each tried to scam the other; but ended up deciding to work together to scam people. Chuck realizes that what they're doing is a ponzi scheme, and Gabriel tells Serena that he and Poppy used her to get to Lily; who is the very, very wealthy widow of Bart Bass. He also admits that he has real feelings for her because his relationship with Poppy is all business; and that once they felt they had enough money, he would leave town while she stayed to be a socialite. She planned to buy him out of the scheme but instead of meeting him, she emptied their bank account and went to his hotel to blame the whole thing on him. Finally, he says that the only chance they have of getting the money back is finding Poppy.
Outside, Blair, Nate, and Georgina wait for Serena and Chuck. He comes out and explains that Poppy is the mastermind and Serena follows after. She says goodbye to Gabriel and he leaves. Nate wonders why Poppy would stay in town after what she did and Serena explains that she has to, if she's going to play a victim and blame the whole thing on Gabriel. Chuck adds that they need to corner her with a sap she thinks she can manipulate for money, and they all turn to Georgina. At the VDW's, Lily meets with the Bass business manager, Bruce, to figure out how to handle the situation. Serena arrives home and Lily asks for a moment alone with her. She reveals that she knows about the scam and is disappointed that she didn't come to her. Serena realizes Dan told her and apologizes for not saying anything; but she's going to fix it. Lily orders her to do no such thing, as her reputation will be ruined if the story ever got out. Serena asks what they should do about Poppy, as it was her plan, but Lily still insists that she just let it go. Afterwards, she sits back down with Bruce and he says that they've arranged payouts for everyone except Rufus. Lily suggests that they handle his payout a little differently. Meanwhile, Rufus takes Eric on a walk and shows him the ring. Eric is happily surprised and asks how he's going to propose; as most of the times Lily has been proposed to have been grandiose and romantic. Rufus hesitates before saying he has lots of ideas. At the Waldorf's, Blair attempts to give Georgina a makeover so she can meet with Poppy. However, Georgina remains firm on her principles to no longer scheme and do evil things. Blair argues that Jesus brought her back to entrap Poppy as a way to earn her forgiveness, since she's been seeking it. Georgina listens and then decides that Blair is right. As she goes into her closet to pick an outfit, Blair receives a call from Serena. She tells her that Lily wants her to call of the plan and orders her not to do anything else until she calls her back. At the VDW's, Serena goes into the living room to find Lily having tea with Poppy. Lily explains that Poppy came by to see how they were doing after the Gabriel thing and to tell them that she's going to Miami the next day. Serena whispers to Poppy that she should check her lipstick and she excuses herself to go to the bathroom. Once she's gone, Serena tells Lily that they should call the police. Lily refuses, saying they already agreed that the adult thing to do is to let her and the situation go. At the loft, Dan receives a call informing Rufus that the paperwork for the investment is on the way. Confused, Dan says he thought that deal wasn't happening but Bruce says that he should begin to receive dividends in about six weeks. At the Waldorf's, Serena arrives and tells Blair that they're going through with the plan. Blair shows her the new Georgina, who introduces herself as Sherilyn Phillips; the daughter of a rich oil owner who is excited to make a new friend in New York.
The next day, Chuck looks over the new Georgina and decides she'll do. Nate asks if they're sure this is a better plan than calling the cops and Serena replies that it's better than Lily's plan to do nothing. Chuck explains that Georgina has a recording device in her bag and once they get a tape of her talking money, they can blackmail her into giving the money back. Nate wonders how they're sure she'll even show up, and Blair responds that she thinks Gabriel took the fall so she's in the clear to do what she wants. On the way out of the Waldorf's, Dan calls Serena to ask about the dividends. She tells him that she's taking care of it and hangs up on him. At the VDW's, Rufus and Jenny arrive, carrying all of Lily's favorite things that he is going to use before he proposes. He admits he's nervous and Jenny encourages him, saying that his proposal is special because it shows that he really loves her and knows who she is. Lily then arrives home and Jenny escorts her upstairs to buy Rufus time to set up. At the Russian Tea Room, the gang and Georgina arrive. Nate asks for a moment to talk with Chuck outside about Blair. He tells him to either man up and tell her how he feels or let her go so they can have a real relationship. At the VDW's, Jenny is filling Lily in on the plot of Twilight to distract her until Lily's phone starts to ring. Rufus motions that it's set up and Jenny leaves. Lily answers the phone to find Dan on the other end, asking about the dividends. Lily says that she got his money back and put it in a mutual fund that will pay him dividends monthly. Dan then asks what Serena is doing at the Russian Tea Room and Lily calls Serena immediately to tell her to stop whatever she's doing. Lily orders her to stop again, but Serena apologizes before hanging up on her. Right after, she makes another important phone call. While Rufus is looking for something, he stumbles upon Lily's files on repaying the scammed victims. He finds his name and learns she has scheduled a $5,000 a month dividend for him. Meanwhile, Poppy arrives at the Russian Tea Room and sits down with Georgina/Sherilyn. While they talk, Blair and Chuck watch from the bar. She asks him if what he feels for her is real, or if he sees it as just a game. He replies that it's just a game and she's free to go if she wishes. She leaves and Serena asks him why he let her go. He answers that he while he loves her, he can't make her happy.
Back at the table, Georgina is fascinated with Poppy's philanthropic side. She says she would love to be a part of something like that and her father would like it to. Poppy says that if she can get her a payment that day, she can find a way to get her in. Excited, Georgina offers to call the bank to set up a wire transfer but Poppy says that since it's so last minute, she can only accept cash. Back at the bar, Nate tells Serena that police just pulled up. Confused, Serena says she thought Chuck was calling his PI; but Blair says he left but so long as they have the recording, the police will be fine. Serena goes outside to talk to the police as Georgina pulls an envelope of cash from her bag. She tells Poppy that it's her emergency money and asks to text her dad for more money. Poppy says that that amount is fine and takes it. Georgina receives a text from Blair asking if she's ready. Georgina says God intended for them to meet and Poppy says she'll call her later before taking off. Outside, the police arrest Serena just as Blair comes out to see what's going on. Nate also come out and they try to tell the police they have the wrong girl. They reply that they don't and put Serena in the back of the car. Serena yells at them to call Chuck as they drive away. While they watch, Poppy sneaks out the door and walks away. Blair goes inside and accuses Georgina of sabotaging the plan to have Serena arrested. Georgina panics and says that if Poppy got away, she stole the money she was given by the camp to buy bibles with. Blair doesn't believe her and reiterates that she's evil through and through. At the VDW's, Rufus confronts Lily about the files. He also asks about the bags of money matching their investments and she admits the deal didn't work out. He then asks about her different plan for him, to give money behind his back every month. She explains that she was just trying to help because it's so hard for her to see him agonize over not sending Dan to Yale. Her phone rings and she excuses herself. At the police station, Serena tries to explain that they were supposed to arrest Poppy for fraud. The cop uncuffs her and removes the bracelet Lily gave her, saying she stole it. Shocked, Serena says that she didn't steal it and tells them to call Lily to confirm that. The cop replies that Lily was the one who called it in. Back at the VDW's, Lily hangs up with the police and tells Rufus that Serena was arrested; because she made it happen. Rufus wonders why she would do that and Lily explains that she had to get Serena away from the situation. However, he doesn't think she handled it the right way and she replies that she doesn't want to talk about it anymore. She notices everything he set up and asked what it all is. He answers that it was a mistake and leaves.
Meanwhile, Chuck arrives at the police station and goes in to talk with the police. Nate and Blair go outside and she admits that she doesn't think they should move in together. He agrees and says he was using the apartment to force their issues but he thinks it's too big of a step. She laughs that a more appropriate step is for him to ask her to prom and her phone rings. Georgina is on the other end, talking in the cold way she used to. She informs Blair that she's taking care of what she and everyone else couldn't. Blair says that Jesus wouldn't approve of that and Georgina simply tells her to inform Jesus that the bitch is back. It's revealed that she's sitting in a car waiting for Poppy's car to leave so she can follow it. At the VDW's, Lily drinks wine alone after her fight with Rufus. At the loft, Rufus gives Dan and Jenny the ring back, and tells them to return it for him. Outside the police station, Nate, Chuck, and Blair work to get the police to let Serena out of jail. Nate and Chuck call different connections to find answers while Blair tells detectives that the bracelet in question has been in the family for years, so it couldn't be stolen. Inside, Serena gets her mugshot taken.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald
- Ed Westwick as Chuck Bass
- Jessica Szohr as Vanessa Abrams (Credit only, as she does not appear in the episode)
- Taylor Momsen as Jenny Humphrey
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Michelle Trachtenberg as Georgina Sparks
- Connor Paolo as Eric van der Woodsen
- Tamara Feldman as Poppy Lifton
- Armie Hammer as Gabriel Edwards
- John Bolton as Bruce Caplan
- Heart's a Mess by Gotye
- Oh Oh Oh Oh Oh Oh Oh Oh by Say Hi
Georgina (after being offered alcohol by Chuck): No thank you. The Lord cannot enter a body solely by alcohol.
Chuck: Good. Because I like to be the one doing the entering.
Serena: I'm so glad you came, B, thank you so much for... for bringing Nate.
Blair: I'm just as flummoxed as you are. I got out at 53rd and made a run for it but he's faster than he looks.
Blair (on feelings): They get you all confused, then they drive you around for hours until they drop you right back to where they started.
Chuck (to Georgina): Why is it that when you say "ritual" I think human sacrifice?
Dan: Well, Serena told me not to say anything-
Lily: Oh, that's my least favorite sentence. Start talking.
Georgina: I gave up my old ways when I let Jesus take the wheel.
Blair: That is a Carrie Underwood song, not a life choice.
Blair: If you cut revenge out of the bible, there's not enough pages to make a pamphlet.
Nate (on Chuck's feelings for Blair): You know what? What I couldn't figure out is why you went out of your way to lie to me about how you felt. But then I realized you weren't lying to me, you were lying to yourself.
Chuck: That is a wonderful theory you've concocted, Nathaniel. You should have it published. Now, if you'll excuse me-
Nate: No, no, no, look. You had your shot and you blew it. So why start toying with her again? If you want her, then man up and tell her. Otherwise, you gotta cut her loose. You gotta cut her lose, and you gotta do it for real this time because I want her!
Chuck: Listen, Blair-
Blair: No, me first. Nate's waiting for me to give him an answer.
Chuck: I heard.
Blair: Do you want to know what's stopping me? I can't answer his question while I'm waiting for you to answer mine. The one I asked you forever ago. What are we, Chuck?
Blair: Last fall, you said we couldn't be together. And I believed you. But every time I try to move on, you're right there. Acting like...
Chuck: Acting like what?
Blair: Like... maybe you want me to be as unhappy as you are.
Chuck: I would never wish that on anyone. I want you to be happy.
Blair: Then look down deep, into the soul I know you have, and tell me if what you feel for me is real... or if it's just a game. If it's real, we'll figure it out. All of us. But if it's not... then please, Chuck, just let me go.
Chuck: It's just a game. I hate to lose. You're free to go.
Blair: Thank you.
Serena (after Blair leaves): Chuck, why did you just do that?
Chuck: Because I love her. And I can't make her happy.
Lily (on having Serena arrested): I asked her to stop and she purposely disobeyed me. Look, this is the only way that I could protect her.
Rufus: From what, Lil?
Lily: From creating a scandal. From ruining her future, and everything that she's worked for. Embarrassing me.
Rufus: You just sounded exactly like your mother.
Georgina (to Blair): You can tell Jesus that the bitch is back.
- The episode title is based off the movie Star Trek: The Wrath of Kahn.
- This is the last appearance of Gabriel Edwards.
- The episode takes place on May 10-11, 2009.