Seder Anything is the 21st episode of the second season and the 39th overall.
When you lose hope in a dream, sometimes all you're left with is sleepless nights. While some call the doctor for a refill, I find the best solution is a full social calendar.
Serena returns from her trip to Spain with a secret. Blair makes a secret deal with Nate's grandfather, William, and Nate learns some disturbing information about his father's arrest. Dan takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover Seder at the Waldorf penthouse with several of his friends and family as guests.
Blair has a dream where she plays both a poor girl striving to go to college and a wealthy socialite, who dismisses the hopes and dreams of the poor one. She wakes up and remembers that she was invited to Nate's cousin Tripp's wedding. Downstairs, Cyrus is preparing for a Seder dinner that he is throwing. While he cooks, she shows him photos of her and Nate since they've gotten back together. Eleanor reminds Blair that the dinner is very important to Cyrus but Blair says she can't make it due to going to Tripp and Maureen's rehearsal dinner. She explains that Nate has a surprise for her and she hopes it has to do with the position for the Junior Committee for the Whitney, since Maureen promised to help her get on. Eleanor warns her to get serious about her future but Blair adds that Maureen is well connected philanthropically and she is looking for an assistant. Cyrus says he's friends with a higher up at NYU that owes him a favor but Blair rudely turns him down, saying she isn't going to waste time there. She then leaves to get ready to meet Nate. At the VDW's, Serena arrives home from Spain and is greeted by Chuck. He informs her that he saw Poppy last week and it's odd how she could have been there and still in Spain with Serena and Gabriel. Meanwhile, Nate and Blair meet at the church where Tripp and Maureen are getting married. Nate excitedly reveals that his surprise is that he got into Columbia University. Surprised, Blair says she didn't know he applied and he explains that he wanted to see if he could get in without his family's help. Maureen then comes up and tells Blair that the Whitney Junior Committee felt she was too new on the scene to join so they gave the position to Elizabeth, one of her bridesmaids. When she's gone, Nate tells her that she had to choose her bridesmaids from a list William provided. The rehearsal begins and Blair takes a seat while Nate goes up front.
At the loft, Dan arrives home to find Jenny and her science partner, Wes, working on their science project. Wes takes the opportunity to leave and says he'll call her later. When he's gone, Dan mentions that he hopes their relationship is strictly professional and she admits that she's working on changing that. Rufus comes into the room then and confesses to them that no one is interested in buying art anymore. Dan asks to please help pay for his own tuition but Rufus tells him to continue focusing on school. He leaves to go shopping with Lily and Jenny mentions that Wes' mom owns a catering company. She offers to call Wes and see if he can get Dan a job; plus she can then ask him to dinner as thanks for being so cool. At the church, William comes to sit next to Blair. He reveals to her that he knows Nate got into Columbia but that he truly believes Yale is the right choice for him. He then asks her about the Junior Committee for the Whitney and she admits she wasn't accepted. William offers to call the chairwoman and have that cleared up right away because there is nothing he wouldn't do for a friend of his grandson. Blair mentions that Yale is an amazing school and that Nate would look dashing in the schools colors; if she can be a bridesmaid. William smiles that Maureen has room for one more and offers his hand to Blair to escort her upfront. At the Waldorf's, Cyrus receives a call from Serena; saying she thinks she needs a lawyer. At the VDW's, Rufus and Lily arrive home from shopping. Hearing her mother home, Serena emerges from her room, dressed to go out. She apologizes but Lily says she's furious at her for trashing the apartment and then running away to Spain. Lily replies that the old Serena is unfortunately back and that she should take her coat off because she's grounded. She goes upstairs and once she's gone, Serena calls Blair, who is at a fitting for her bridesmaid dress before the rehearsal dinner. She asks if Blair will be home anytime soon and when she learns that she won't be, sneaks out of the apartment. Meanwhile, Dan arrives with Corinne, another caterer. They begin unloading the van and Dan realizes that they were hired for by the Waldorf's. He tries to get out of it but Eleanor offers to double the pay for both him and Corrine if he stays. He grudgingly agrees to help, especially after hearing Blair won't be at the dinner. At the Archibald's, Blair receives confirmation that she was accepted into the Junior Committee and happily greets Nate. She tries to uptalk Yale but Nate remains firm on his decision to go to Columbia. He continues that he wants nothing to do with his family and after that night, he's done with them forever.
That night at the Waldorf's, Cyrus' mother arrives while he meets with Serena. They finish and he promises to look into the legalities of her situation but that he thinks she should tell Lily. She admits that telling her mother she accidentally got married in Spain but is getting an annulment wouldn't sit well with her. Cyrus excuses himself to go to Eleanor, who is calling him, and Dan reveals himself, having heard what she did. Upstairs, Serena explains to Dan that two days into the trip, Poppy and Gabriel got into a huge fight and she went home. After she was gone, a thing between her and Gabriel began. They attended a dinner where they got drunk and maybe got married in front of a priest. She asks if he's jealous and he admits that the fact that she married someone else so quickly is a bit insulting. He then says he has to get back to work and Serena realizes that he's serving the Seder. At the rehearsal dinner, Blair asks Nate what's going on and he simply says that he's glad she's there with him. Blair tells him to not say anything to William about Columbia yet and Nate says that will be easy because he isn't going to talk to him. William comes over and Nate gives him the cold shoulder as he walks away. He asks Blair if there's a problem and she nervously says no, that she just needs a few minutes to finish her task. At the Waldorf's, Rufus and Lily arrive at the Seder. Eleanor almost asks if he knows Dan is there, but then says that he'll find out. Rufus then notices Allan Levy, a famed art collector, speaking to Cyrus. Lily says that she knew he was coming so she got them invited so he could meet him. Rufus thanks her but says that he isn't going to fall over himself to impress someone like Allan. He then notices Dan come downstairs and asks what he's doing there. Serena comes down and says that Blair asked her to come so she asked Dan. Lily says that she doesn't want to cause a scene so they can talk later. Rufus laughs that Dan is dressed like a cater waiter and Dan replies that that's what happens when you go for a classic look. Eleanor comes over and asks what Serena is doing there. Lily explains that Blair invited her and Eleanor confusedly says that Blair made it clear she wasn't coming. She orders Dan to get the wine and to make himself presentable and he goes to follow her instructions. At the VDW's, Jenny has sliders with Wes while they set up to play Monopoly. He says that he can't believe she is the same girl who used to hang on the Met steps and she shyly says that people change. Chuck then enters the apartment while making out with a random girl. He tells them not to be alarmed if they hear screaming and takes her to his room. Back at the Waldorf's, Lily tries to strike up a conversation between Allan and Rufus but doesn't succeed. Serena apologizes to Dan for everything but he says he can't focus on that because he has a job to do.
At the rehearsal dinner, Blair asks Tripp if he said anything to Nate. Tripp reveals that Nate feels blessed that they're back together and he's happy that the two of them have changed for the better. He asks Blair if she feels they're better for each other now and she says yes. He tells her to be good to him and walks away. Meanwhile, Nate begins his best man speech. In it, he reveals that he just found out that William is the one who had his father investigated, and subsequently, arrested. He finishes by warning Tripp to watch his back and ends the speech. Back at the Waldorf's, Dan is getting more linens when the elevator opens. Gabriel steps out, introduces himself, and claims to be looking for Serena. Dan goes to the dining room and whispers to Serena that she needs to come out to the foyer. She initially says no but then agrees to go when he tells her to again. She goes out and sees Gabriel. He explains that he came to see her because she disappeared from Spain and a guy at her apartment said she would be there. She tells him that he's crashing a private event and that he has to go. He demands to know why she won't even talk to him and she blurts out that Dan is her boyfriend. Dan plays along but Gabriel doesn't believe them. Eleanor emerges and greets Gabriel. He apologizes for interrupting and she invites him to join. He accepts the invitation and goes into the dining room. Back at the rehearsal dinner, William asks Blair if she knew about what Nate did. She swears she didn't and he tells her that he has five minutes to fix it, because she needs to remember what she has at stake. Back at the Seder, Lily asks Gabriel if he went to Spain with Serena and Poppy. He says yes and Serena interrupts to tell Cyrus that the wine is delicious. Allan Levy asks Rufus if his artists are worth attention and Rufus says they all are. Dan comes in to serve wine and Gabriel asks why he's serving it. Serena quickly says that he's just helpful and helps him into the chair next to her. She grabs his hand and Lily sees it. Realizing that they're most likely back together, she whispers it to Rufus, who mutters that she has to be kidding him.
At the VDW's, Chuck is about to have sex with the woman when he realizes that he's done it with her before. He excuses himself to get a drink and goes out to the kitchen. He makes a comment to Jenny about Monopoly and she asks Wes to go for a walk. He agrees and she says she'll meet him at the elevator. Once he's out of earshot, Jenny tells Chuck that he shouldn't make everyone miserable just because he is. Chuck replies that she doesn't live there yet and she says that if she ever told Rufus about the Kiss on the Lips party (Pilot) that he would make Lily choose between them and Chuck. He affirms that he doesn't care if Lily kicks him out but Jenny says that he would care because the only people who care about him are the VDW's. The woman comes out and asks if he's coming back. He tells her to let herself out. At the rehearsal dinner, Nate apologizes to Blair for making a scene and not telling her. She asks if he's okay and he admits he's not, because he feels it was wrong to trust William. She tells him that he's wonderful and that she's going to get her coat so they can go. When she's gone, William explains to Nate that he only turned Howard in after he lied about having a problem and doing anything wrong. He continues that he only did so to prevent further damage to Anne and Nate. Nate asks why he couldn't have just told him that from the beginning because he's sick of everyone going behind his back and lying to him. William offers to have them start again and tells him about his deal with Blair. At the Seder, Eleanor is becoming increasingly agitated at not being able to eat. Rufus asks Dan and Serena when they got back together, and Lily adds that they just broke up two months ago. Gabriel says that he thought they broke up right before Spain and he's confused on why no one knows they're dating. Lily finally asks Serena what is going on and Dan announces that he is a cater waiter so they're pretending to be back together to cover for him. Rufus asks if that's him trying to help with Yale and Dan says yes. Lily asks for a word alone with Serena.
Outside the rehearsal dinner, Nate tells Blair to go home because he needs some air. She asks what's going on because she's proud of the way he handled things there. He asks her if she told William she would convince him to go to Yale in exchange for being a bridesmaid. She admits that she did but Nate says that first William sold his father out, then she sold him out for a picture in the newspaper. He sadly says that he thought that this time their relationship would be different but she's the same girl she always was. She begs him to give her another chance and he replies that he can't think of a single reason why he would. Back at the Waldorf's, Lily confronts Serena about making a scene. Serena says that she knows she's hurt people and made mistakes but she misses the freedom her old life gave her. She wonders how to find a balance between the two in addition to handling Lily thinking she's a bad person every time she messes up. Lily says she could never think of her as a bad person and that her acceptance letter to Brown came while she was away. She congratulates her and the two hug. Lily asks what she's going to do about Gabriel and Serena admits that she likes him but it's become a big mess now. Corrine comes in and says that he just left. Outside, Serena stops Gabriel and apologizes for lying. She also says that she's not ready to be married and Gabriel smiles. He says that they're definitely not married, and it probably wasn't even a priest that "married" them. Relieved, she admits that Dan isn't her boyfriend and Gabriel asks about himself. They begin to make out until Blair arrives. She tearfully dives into Serena's arms and they hug. At the VDW's, Nate goes to see Chuck. He tells him about the night and Chuck tells him that he shouldn't want Blair to be anything other than what she is. He realizes his glass is empty and Nate offers to go get them refills.
Back at the Waldorf's, Lily thanks Dan for helping Serena. Rufus comes in and announces that not only did he sell Allan Levy a painting, he realized he wants to sell the gallery because he no longer enjoys selling art. Dan asks what he's going to do next and Rufus says he doesn't know but that he's excited to find out. Upstairs, Blair vents to Serena about what she did. She wonders what she's going to do and Serena promises that she'll figure something out. Blair asks Serena who the guy she was kissing was and she says that he is a long story. Eleanor then comes in and says there is someone downstairs who wants to speak to Blair. She realizes that she should probably apologize to Cyrus for earlier and goes down. Back at the VDW's, Chuck comes out of his room to find Nate gone and their two empty glasses on the counter. Jenny comes in and says she's looking for Rufus so they can go home. He asks how her date was and then apologizes for what he did to her. He also says that if she ever did move in, he would make sure he's not around. Back at the Waldorf's, Blair apologizes to Cyrus for missing the Seder and for being snotty about NYU. She asks if he could call in a favor at NYU and he forgives her. As they hug and make up, Blair notices Nate standing in the background when he says they'll both be in the city for college. Eleanor and Cyrus excuse themselves and Blair tells Nate how sorry she is before hugging him tightly. They kiss and make up. Upstairs, Serena leaves Gabriel a message saying that she doesn't know what's going to happen with them but she's glad he came back for her. Elsewhere, Poppy sees the notification for the voicemail on Gabriel's phone and as he's taking off his coat, she demands to know everything.
- 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
- Margaret Colin as Eleanor Waldorf
- Wallace Shawn as Cyrus Rose
- Tamara Feldman as Poppy Lifton
- Armie Hammer as Gabriel Edwards
- James Naughton as William van der Bilt
- Aaron Tveit as Tripp van der Bilt
- Holley Fain as Maureen van der Bilt
- Tom Titone as Allan Levy
- Will Rogers as Wes
- Right Round by Flo Rida
- Is You Is or Is You Isn't My Baby? (Rae and Christian Remix) by Dinah Washington
- Inside Out (featured in Gossip Girl) by Miss Eighty 6
- Runaway by Yeah Yeah Yeahs
- Whatever Lola Wants by Gotan Project & Sarah Vaughn
- Graffiti Eyes by Stellastarr*
- Peer Gynt Suite No. 1, Op. 46: III Anitras Dans (Anitra's Dance) by Bjarte Engeset & Malmo Symphony Orchestra
Blair: Being a socialite was good enough for Jackie O.
Cyrus: You know, my old friend J.R. is a big mugwump at NYU, and he happens to owe me a favor.
Eleanor: Cyrus saved J.R.'s life in 'Nam.
Blair: Oh. Well, I'm sorry, but just because I lost Yale does not mean I'm wasting my time at a non-Ivy reading Beloved six times and experimenting with lesbianism. Now Nate is waiting.
Eleanor: Waldorf women are NOT socialites!
Chuck (on moving on from Blair): I realized I'm a 17 year old billionaire with tremendous stamina.
Rufus: How did antique shopping turn into shoe shopping?
Lily: Well my darling, all shopping eventually leads to shoe shopping.
Dan: Serena, being Eleanor's bitch boy is about all I can take right now so I really don't need your pity.
Nate: Well, good evening. Most of you know me, I'm Nate Archibald, Tripp's cousin. When Tripp asked me to be the best man at his wedding, I was a little bit surprised, to say the least. But I guess Grandfather told him to choose me and that was that, so. We all know how important family is to William van der Bilt. But what we don't know is the many secret ways he helps us all out. For instance, today I discovered that he was the one who had my father investigated by the authorities. And if he cares so much about family... why did he destroy mine? So... I guess the lesson here: Tripp, old buddy... just watch your back.
Nate (to Blair): I want to trust you... but I can't think of a single reason why I should.
Nate: It's stupid of me to think Blair changed.
Nate: So... she's just the way she is.
Chuck: What I mean is, it's stupid of you to want her to be anything other than she is. Anyway, Blair is changing.
Nate: How do you know?
Chuck: Because she could of had me. She chose you. Now she just needs someone to believe in her.
Blair: I can't believe I sold out Nate to be the next Jackie O.
Serena: Yeah, I always pictured you as the next Hillary.
- The episode title is based off the movie Say Anything.
- The episode takes place April 18th, 2009.
- The photo of Blair and Nate at the Young Fellows ball is a photo that was originally taken in Hi, Society at Cotillion.
- St. Joseph's Church, where Tripp and Maureen plan to marry, is where Blair eventually marries Prince Louis Grimaldi.