The Empire Strikes Jack is the 16th episode of the third season and the 59th overall.
"They say the clothes make the man, but who makes the clothes? On the Upper East Side, it's Eleanor Waldorf. And we hear her new line is to die for."
Chuck finds himself once again at odds with Jack when Chuck learns that his mother, Elizabeth, has betrayed him. Meanwhile, Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with Eleanor’s fashion show, but the opportunity takes a big turn for the worse when Jenny learns that her old frenemy, Agnes, will be one of the models. Elsewhere, Dan and Vanessa announce their newfound romance to everyone and try to have a real date when Vanessa cooks dinner at the Humphrey loft to get out of a rut.
The episode begins with a quick slideshow of the Waldorf penthouse filled with workers making new clothes. Meanwhile, Rufus and Jenny are taking a walk and he announces to her that he got her a job working at Eleanor's upcoming pop-up fashion show. Jenny, remembering the last time she worked with Eleanor, is hesitant at accepting but Rufus encourages her to try anyway. They then arrive in the Waldorf's penthouse, and Jenny thanks him for getting her in. At The Empire, Blair arrives to see Chuck and is excited about the fashion show that night. She asks him to come uptown with her, but Chuck tells her he already has plans with Elizabeth. He raves to Blair about how Elizabeth is a natural at running the hotel and he trusts her with the job completely. She wishes him a good day and leaves to go see Eleanor. When she's gone, Empire security arrives in Chuck's suite to have him removed from the premises immediately. Chuck explains that while Elizabeth might be in charge, he's still going to be living there, but the men reply that the orders for him to leave came from her.
At the Waldorf's, Jenny approaches Eleanor and thanks her for letting her come back. She promises not to let her down, and Eleanor tells her that she rehired Agnes to give them both second chances. Agnes tells them that she's 90 days sober and in AA. Eleanor instructs Jenny to get her fitted and walks off. At the VDW's, Dan and Vanessa are heading up to join Rufus, Nate, and Serena for breakfast. They try prepare to tell everyone they're dating, but find Nate and Serena already told Rufus, who thinks it's great. Back at the Waldorf's, Eleanor tells Blair that Mr. Conwell, the CEO of Conwell's department stores, is coming to New York to see the show. She elaborates that Conwell's is the largest retailer in the country and her first choice to carry her new junior line. Blair is unenthused with the idea, and asks why she can't have her line in higher fashion stores. Eleanor replies that high fashion has fallen on hard times and she could potentially have her line in over five thousand stores. She then has the idea for Blair to bring all her college friends to the show to give off the message that normal girls would like the clothes. Blair tries to get out of it, but Eleanor refuses to back down and tells her to bring ten or twenty. She goes off to do something, and Dorotea asks Blair what she's going to do since she has no friends. Blair then has an idea and says there is one person at NYU who can help. At The Empire, Elizabeth comes up to Chuck's suite to explain but is interrupted by the arrival of Jack, who takes over explaining. He informs Chuck that he was played from the very beginning and that it's now time for him to leave. Chuck leaves with security, but not before he gives a glare of betrayal towards Elizabeth.
At the VDW's, Serena tells Vanessa how happy she is for them. They agree that dating old friends is fun but can sometimes be unexciting, so Serena advises Vanessa to not fall into a rut. Nate asks what their plans are for the night, and Dan answers that their Saturday routine is to watch a movie at the loft and have the same dinner. Back at the Waldorf's, Jenny is becoming increasingly frustrated with Agnes' uncooperative behavior. She apologizes for stealing her contacts and betraying her, and Agnes apologizes for burning all the dresses up. They hug and make up, and Agnes sees a text from Damien on Jenny's phone. She pushes her to tell, and Jenny fills her in on the situation, including how he's now texting her nonstop for his pills. When Jenny goes to fix her hem, Agnes takes her phone and invites Damien to come to the Waldorf fashion show to get the pills. When he agrees and they hang up, she tells Jenny she can just lead him on and then flush the pills away right in front of him. Jenny then admits it's kind of a brilliant plan. Back at the VDW's, Vanessa asks Serena advice on how to liven things up and Nate suggests they role play. Serena agrees it's not a bad idea, and adds that she could recreate a scene from one of his favorite movies. Vanessa tells Dan to come to the life at 6:30 and they both leave. Before Nate and Serena can leave, he gets a text from Chuck and tells her they need to find him right away. Back at the Waldorf's, Eleanor picks up some of Jenny's work and admits she forgot how talented she is. She tells Jenny that after the show is over, they need to have a talk about finding her a more permanent position with Waldorf Designs. Jenny thanks her, and then another worker, Callie, brings Jenny the pills from her room like instructed. Agnes comes over and Jenny confesses that she's not so sure she wants to go through with the Damien thing now because she doesn't want to risk her fashion future. Agnes says it's okay and she was only trying to help. Meanwhile, Blair, Nate, and Serena meet up with Chuck at a bar. He tells them the events of the morning, including Jack and his lawyer's part in everything. He says his only hope is talking to Elizabeth alone, since this obviously isn't her idea and Jack has something on her. He leaves, and Nate and Serena speculate whether Elizabeth is even his mother. Blair tells them he had a DNA test done, then leaves to prepare for the fashion show. In the NYU dorms, Dorota waits for Brandeis, and asks about her hourly rates and if she has thirty friends available. Back at the Waldorf's, Callie asks Jenny to bring some racks downstairs and she agrees. When they leave, Agnes grabs the pills from Jenny's bag and sneaks off with them.
At the fashion show, Brandeis and her friends arrive. Serena and Blair are discussing Chuck when Serena sees Brandeis. They talk briefly before Blair instructs her to target Mr. Conwell, and to bring her friends along with her. When she walks off to see him, Serena asks Blair why she couldn't just tell Eleanor she has no friends. Blair doesn't have a good answer and walks away. At the loft, Vanessa wakes Dan up from sleeping with a kiss, then reveals she made dinner and decorated the dining area to resemble Rear Window. Back at the fashion show, Jenny is directing the models when she notices Agnes carrying the pills around. When confronted, she insists it's just a little party but Jenny is determined not to let her ruin the show. She tries to tell Eleanor, but she's too busy to listen. In the background, Agnes tells Callie and her friends to put Jenny to bed early. Meanwhile, Chuck meets with Elizabeth somewhere private. He offers to double whatever Jack has on her, but she refuses and says it was never about money. She explains that she and Jack love and need each other, but Chuck isn't buying it. After several attempts to unsuccessfully convince her otherwise, he leaves empty handed. Back at the fashion show, Serena tells Nate about Blair hiring prostitutes to act as her friends. He then gets a call from Chuck, telling him about his meeting with Elizabeth. Nate has an idea, and asks if Chuck can get Jack to the fashion show. At the loft, Vanessa feels like Dan is disappointed with the dinner and asks if he would have rather done what they always do. He insists that's not what's happening, then suggests they go to a film they like at NYU. She confesses that she's trying to get them out of their rut, but he's confused since they just started dating. Rufus then comes in, and apologizes for ruining their date. Vanessa asks him to stay and says that them hanging out like usual is exactly what Dan wants. She walks out, and Rufus asks Dan what's going on. Back at the show, the models have begun walking and Blair tries to uptalk the line and Eleanor to Mr. Conwell. He agrees that the clothes are beautiful, but his stores will never carry Eleanor's line because he knows prostitutes are there and that isn't the clientele he wants to attract. Meanwhile, Jenny watches from backstage and is offered a glass of champagne by Callie. She gladly takes it and begins drinking. Agnes comes back and asks Callie if she gave her one or two. She answers three.
Soon after, Jenny begins to feel the effects of the drugs and realizes Agnes drugged her. Agnes says she needed some sort of revenge for the year before and Damien's drugs fell into her lap. She begins blaming Jenny for ruining their business and then walks away. Outside, Jack finds Nate and asks where Chuck is. Nate directs him to the bar, where he and Serena watch him flirt with every woman who approaches him. They agree to wait for Jack to be Jack and continue watching. At the loft, Dan, Vanessa, and Rufus eat flan while awkwardly talking about Vanessa's setup. Vanessa excuses herself and leaves the loft. When she's gone, Dan tells Rufus about her not wanting to fall into a rut and Rufus advises him to just try and talk things through with Vanessa. Back at the show, Blair finds Brandeis and confronts her about outing herself as a prostitute. Brandeis says that she didn't try anything with Mr. Conwell, but her male friend Julian, who is also a prostitute, is there too. She explains that Mr. Conwell and Julian hook up every time he's in town and they had plans to get together later. She apologizes and so does Blair. Afterwards, Blair chases down Mr. Conwell and blackmails him with the information about Julian. He agrees to take another look at the line. Meanwhile outside, Nate and Serena plot to take photos of Jack with prostitutes and show them to Elizabeth to prove he doesn't love her. However, when they open the car door where Jack is supposed to be, they find he figured out their plan and isn't in a compromising position at all. They leave, and Serena heads back inside to find Blair. Nate stays outside to call Chuck, but witnesses Agnes and her friends getting into a taxi with a drugged Jenny. They plot to get her laid and take off.
Agnes and her friends bring Jenny to a bar and decide to leave her with a group of guys having a bachelor party. She tells them to make sure she has a good time and leaves. Back at the show, Blair brings Mr. Conwell to Eleanor and he tells her that Conwell's would be honored to sell her things. Eleanor is happy until he explains that some alternations will need to be made: including dropping the name Eleanor Waldorf from the clothes. She refuses to do so, and kills the deal. He leaves, and Blair asks what she's doing. Eleanor tells her that she would rather lose the deal than lose herself, then advises Blair to never hide who she is. Blair then admits that everyone at NYU hates her and she has no friends. She also admits that her "friends" at the show are prostitutes, and that while she tried, she hates NYU and can't fit in. Eleanor hugs her and tells her that it's okay that she doesn't fit in everywhere because one day she'll find the place she does. Back at the bar, the guys plan to leave without doing anything to Jenny. One asks if they're going to leave her, and another answers that they'll just tell a bartender to call a cab. Meanwhile, Jenny's phone rings and she answers to find Nate on the other line. He asks where she is, and she answers that she doesn't know. He uses his phone to track her location and promises to be there soon to get her. At NYU, Dan arrives in Vanessa's dorm to talk. He asks what happened, and she admits that they don't do anything different than when they were friends. Dan listens, then says nothing they do is the same and he wants to take her on a romantic second first date. She asks where, and she says it's a surprise. Meanwhile, Chuck meets with Elizabeth and she tells him that she signed the hotel over to Jack. She also says she made Jack choose between her and the hotel and after he chose the hotel, she decided to leave the city. Despite everything, Chuck asks her to stay. She then admits that she isn't his real mother and she has no knowledge of who his real mother is. He replies that she's right, because his real mother could have never done to him what she did, and walks away.
Back at the bar, Nate overhears someone talking about Jenny and demands to know where she is. Meanwhile, a guy from the bachelor party tries to feel her up and offers to take her somewhere more quiet. Before they can leave, Nate walks in and saves her from the guy by leaving with her. He takes her home to the VDW's, and by the time they get there, she's sobered up a little. They meet up with Rufus, who asks how the show is. Nate explains that there was no cabs so he walked her home. Jenny says she's exhausted and heads off to bed. Rufus thanks Nate for walking her home and goes back upstairs. Back at the show, Blair tells Serena that she told Eleanor about hating NYU. While they talk, some freshman girls from Columbia approach Blair and announce they thought she was dead. Confused, Blair asks what they mean and they say that they hadn't read about her on Gossip Girl for awhile. Surprised, she asks again if they read Gossip Girl, and they answer that everyone at Columbia does. Blair compliments one of the girls' shoes, and fixes her headband to her liking. She thanks her, and the group walks away. Back at the VDW's, Nate brings Jenny her purse that she forgot and finds her sitting alone in the dark. He asks if she's okay, and she asks what's wrong with her. She continues that she doesn't know how she ended up where she did, and he tells her that things haven't been easy for him, but he's happy with Serena now. He promises things will turn around for her too, and then her phone rings. She looks at it to find a text from Eleanor congratulating her on the night and inviting her to lunch the next day. He tells her that she needs to learn from this, and she thanks him for the night. They hug and he leaves. At the NYU dorms, Dan and Vanessa sit and eat pirogues. She asks if that's his idea of a romantic date, and he explains that getting to do all the things they used to do but with her as his girlfriend is the most romantic thing he could think of. Vanessa likes that answer and they kiss. Elsewhere outside, Nate and Serena happily kiss. At the VDW's, Jenny reads the night's Gossip Girl article on how Serena and Nate are The Golden Couple. At The Empire, Jack calls Elizabeth before she leaves and she explains that she is leaving to become the person she forgot. He reminds her that she just ruined her relationship with her son but she isn't fazed. Before she leaves, she takes one last look at her locket: one side with a picture of Bart and the other with her and newborn Chuck. At the NYU dorms, Chuck comes to see Blair. She asks if he's okay, and he tells her Elizabeth is gone and the hotel is lost forever. He tells her that he isn't upset because he never needed his mother before now and never will. She replies that if it's war Jack wants, that's what he'll get. They kiss.
- 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
- Taylor Momsen as Jenny Humphrey
- Kelly Rutherford as Lily van der Woodsen (Credit only, as she does not appear in the episode)
- Matthew Settle as Rufus Humphrey
- Margaret Colin as Eleanor Waldorf
- Zuzanna Szadkowski as Dorota Kishlovsky
- Desmond Harrington as Jack Bass
- Laura Harring as Elizabeth Fisher
- Willa Holland as Agnes Andrews
- Scott Bryce as Ed Conwell
- Falling Down by Scarlett Johansson
- Run by Vampire Weeked
- Between Two Lungs by Florence + The Machine
- Not Exactly by DeadMau5
- Hi Friend! by DeadMau5 (feat. MC Flipside)
- Hollywood by Hollywood Holt
- Animal by Far East Movement
- I Remember by Deadmau5 (feat. Kaskade)
- Go Hard or Go Home by Megha Maan
- FML by DeadMau5
- Try to Find by Danica
Rufus (to Jenny): Jen, as hard as it is for me to admit, there are some things more important in life than waffles.
Blair: Nothing says luxury quite like your own private army.
Jack (to Chuck): You've been played, Chuckie. From the very beginning.
Blair: Prostitutes are people too. Plus they have a lot of disposable income.
Chuck: I don't know what my uncle has promised you but I'll double it if you give me my hotel back.
Elizabeth: Oh, Chuck. This was never about money.
Chuck: Then what does Jack have on you? It must be something big for you to do all this.
Elizabeth: I love him. I know it's very difficult for you to understand, but-
Chuck: Jack is incapable of love! He is USING you! He is stealing my hotel and then he will leave you.
Elizabeth: I know he's not perfect. But he understands me. He doesn't judge me. Underneath it all, he's a kind, loving person.
Chuck: What kind of "loving person" would convince you to do this to me?
Elizabeth: When we started the game, I told myself that you were just a stranger. But I didn't know how much I'd come to care for you.
Chuck: So help me. Give me back my hotel.
Elizabeth: I can't. I'm sorry.
Chuck: You're sorry? That's it?
Elizabeth: I need Jack. And I believe he needs me too, h-he loves me.
Chuck: If you believe that.. then you deserve whatever happens next.
Rufus (to Dan on his date with Vanessa): Son, I hate to tell you, but this date is a disaster.
Chuck: Stay. Not for Jack, or the hotel... stay for me. I already lost my mother once.
Elizabeth: Chuck... I'm not your mother. I don't know if your real mother is alive or not but I'm sure she loved you very much. And that she's nothing like me.
Chuck: You're right. Because my real mother could have never done to me what you did.
Elizabeth *on the phone*: Did you change your mind?
Jack: I was hoping you changed yours. Perhaps you need to see the view from up here. People really do look like ants.
Elizabeth: How did I ever love you?
Jack: Fair question. But if love won't tempt you, how about money?
Elizabeth: I'm leaving. And I don't want anything.
Jack: Where are you gonna go? You destroyed your relationship with your son. Who else do you have besides me?
Elizabeth: I told Chuck I wasn't his mother. And that he deserves someone much better than me.
Jack: I'll warn you. You're taking off just when it's about to get fun.
Elizabeth: I'm starting over. I'm gonna try to be the person I forgot.
- The episode title is based off the movie Star Wars Episode V: The Empire Strikes Back.
- This episode confirms that the identity of Chuck's real mother is Elizabeth.