Despicable B is the 21st episode of the fifth season and 108th episode overall.
- “In our modern age, there are so many ways for information travel. And yet with all our tablets and smartphones, there are still some people who like to get their morning dish the old fashioned way. Even without the information highway, good news always seems to travel fast. But bad news? Well, you know what they say.”
- —xo xo GOSSIP GIRL
Blair feels like her prestigious reputation might be slipping away and decides to change that herself. Meanwhile, Lily throws a family party and invites William, Carol, and Lola to prove the family is as united as ever and Nate digs into Diana's past.
The episode begins with Blair sending Dan off to a meeting at Simon & Schuster. She gives him tips to success and he leaves. She calls Dorota into the room and tells her to run her a bath so she can catch up on New York Magazine. However, Dorota takes the magazines from Blair and suggests she just take a quick shower and supervise her while she cleans out her closet, citing wanting to work off baby weight and Blair needing the extra room. Meanwhile, Serena and Lily are finishing up at court as an attempt to get CeCe's money away from Ivy. They discuss how CeCe's nurse accused Ivy of taking advantage of the elderly and right then, they knew the judge would invalidate the will. Ivy confronts Lily and Serena, and asks how much they paid the nurse to lie on the stand. Serena tells her to back off before they file a restraining order and the two leave. She asks Lily why Rufus didn't come, and Lily says he had an appointment and didn't want to make him cancel. Serena then asks what happens with the will now, and Lily explains that the estate will now be divided 50/50 between her and Carol, who is coming in that night to sign the paperwork. Outside, paparazzi begin to ask questions. They ask if there's still a fight regarding money, and Lily says the family couldn't be happier. One reporter then asks if it's true that her and Rufus are living apart, and Lily says it isn't true and leads Serena away.
At The Empire, Nate receives a call from Diana. She says that the news of her being Chuck's mother might have come as a shock, but that it doesn't have to change things between them. She adds that now that Nate and Lola have broken up, she suspects he still has feelings for her. Nate says he never thought of himself as a "sleep with his best friend's mother" kind of guy, but Diana insists that they meet and talk everything out. At the VDW's, Serena asks Lily if it's true what the paparazzi said about her and Rufus. Lily replies that they're taking a small hiatus to clear their heads and that's all it is. She goes on to explain how she's more worried about the family's public face instead of what Rufus is doing, but Serena is convinced her problems with Rufus are the bigger issue. Lily announces she's going to throw a family dinner, and invite a reporter from the New York Social Diary. Serena doesn't like the idea, since her and Lola aren't on good terms and that inviting the media over won't fix anything. Back at The Empire, Nate tells Chuck that he was on the phone with Diana earlier. Chuck asks which one it's more awkward for, him or Chuck, and Nate says it's too weird to be in business with her knowing her past with the Bass family. He says he invited PI Andrew Tyler over to give him information on who's funding Diana, and Chuck admits that he isn't sure what kind of relationship he wants with her and isn't ready to put her out of business yet. Andrew arrives and informs Nate that Diana is getting backing from an Australian Company that lists Jack Bass on the board. Nate tells Andrew that his new assignment is to find out anything and everything he can about Diana.
At the Waldorf's, Blair tells Dorota how that for the first time in a long time, it feels as if all is right in the universe. She then spots the New York Magazines in the trash can and asks Dorota why she threw them out. Dorota warns her that there are mean things written about her friends, but Blair isn't fazed. She opens anyway and finds that Dan made the approval matrix for Inside and writing a sequel. She then sees her name on the lowbrow list for being married for less time than Kim Kardashian. She tells Dorota that everything is in fact not right in the universe and that she must become as highbrow as Dan right away. Elsewhere, Serena calls William to invite him to the family dinner. She confesses to him that she doesn't think Lily's plan to show off to the press is the right way to handle things, but William tells her that it's just Lily's process and she needs to make sure everything looks good on the outside before she focuses on the inside. Serena asks him to come, especially since Carol is coming, they need his presence. He declines, citing that he's out of town and there's no way he could make it into the city in time. Serena accepts that, and hangs up. When passing a window, she sees William and Lola together and realizes he was lying to her.
At their breakfast, Lola angrily talks about how Carol should have told her about William being her dad so they could figure out what kind of relationship they wanted to have. However, William admits that he was a bad father to Serena and Eric and that they should focus on their relationship in the future. He says that despite what Carol wants, she can tell everyone if she wants but Lola thinks it's best not to tell the family yet. At the loft, Lily tells Rufus that the will was invalidated and she's there to celebrate with him. She invites him to the family dinner, and that it's time to move on from their fighting. He says that's not a real apology, and she says she doesn't need to apologize and he does for helping Ivy behind her back. He tells Lily to call when she's ready to be a partner in their marriage and shows her the door. At The Empire, Serena waits for William in the lobby. She asks him to explain why he lied to her and was hanging out with Lola. He says he bonded with Lola at CeCe's wake and wants to be there for her since she's lonely. He says he lied abut where he was because he heard the rumors about Lily and Rufus, and he knows that his presence would only hurt their relationship. He apologizes about lying to her, and accepts her invitation to the dinner. Serena also says she's going to invite Lola.
At The Spectator, Nate mulls over the news that Jack left Bass Australia and no one seems to know where he is. Lola arrives to see Nate, and apologizes for the role she played in the reveal of Diana as Chuck's mother. She explains that her real father came forward and she needs someone to talk to. Nate says he understands, since he went through a similar thing with Chuck when Elizabeth Fisher came to town. He realizes that it was all orchestrated by Jack, and apologizes to Lola and tells her that he needs to deal with something right away. She leaves, and Nate instructs an assistant to call Andrew Tyler and to find out anything she can about Elizabeth. Meanwhile, Blair has set up an accessory exhibit as an attempt to become highbrow. She invites a representative from FIT, and shows off the purse she brought to prom and the shoe Louis brought from Paris at the beginning of their fairytale romance. The rep says that maybe if she was still a princess, he would report but she's no longer royalty and they already did a similar story with someone else. He leaves and Dan comes in. Dan says his publisher wanted to tell him in person that he's one of the five people nominated for the New York Public Library's 2012 Young Lions Fiction Award and wants Blair to come with him to the cocktail reception that night. She agrees, and tells Dan she's going to buy a new dress. He reminds her to keep it casual.
Back at The Spectator, Serena arrives to look for Lola. She asks Nate where she is, and Nate says she just missed her. She tells him about the family dinner, and Nate says he thinks Lola could need family around because she spent the morning with her father, and is looking for support. At the loft, Dan reads off a potential speech to Rufus. He offers to go to the party with Dan that night, and Dan suspects something is up with Rufus. He admits he isn't sure he wants to take Lily up on her family dinner reputation. Dan tells him that if Lily is trying to make amends, he needs to also put up effort.
At the VDW's, Serena tells Lily about Lola being her half sister. She explains to Lily her entire morning, and Lily asks if any of them know that they know. Serena says no, and Lily asks her to keep it that way until after the reporter comes and they can all talk maturely after dinner. She instructs Serena to get ready for the party and come back with a happy face, and she agrees. When she leaves, Lily makes a phone call to someone with a potential business proposition. At The Spectator, Nate has been calling Elizabeth Fisher repeatedly wanting answers. Andrew informs Nate that any record of Diana Payne was three years ago and before that, she was basically nonexistent. At The Waldorf's, Dorota notes that Blair looks suspicious as she's very dressed up for a casual event. Blair explains that the highbrow people Dan was listed with are doctors and philanthropists, and no one very exciting and that she wants to be despicably highbrow again. She shows Dorota a list of talking points for when the press calls. Dorota realizes she's going to try and steal Dan's spotlight. At the loft, Rufus has taken Dan's advice and calls Lily to say he'll come to the dinner after all. She lies and says the party was cancelled, but promises to call her later. When she hangs up, Ivy has arrived and wants to know about the partnership Lily proposed.
At the party, Blair takes off her coat and Dan is surprised by the dress she's wearing, saying he told her it was casual. She calls Dorota, and demands to know why nothing about her being there is posted on Gossip Girl yet. Dorota isn't sure, since she already sent the tip in. Blair decides to slip into phase two and hangs up. She approaches Dan and the group he's talking to. She introduces herself as Dan's muse and inspiration. Meanwhile, Nate breaks into Diana's hotel room and begins looking for her secrets. He finds a planner in her dresser but before he can leave with it, Diana catches him. She asks what he's doing, and he pretends he was looking for something for her to wear and couldn't stop thinking about their chemistry. He kisses her and the two have sex. At the VDW's, Lily greets the reporter and says she hopes he can see that the money fight was widely exaggerated by the media. Serena is noticeably unhappy, and Lily reminds her to put on a happy face. Carol arrives and Lily introduces her to the reporter. William arrives, and Carol says that now she got half of CeCe's estate, he's no longer in danger of their affair being exposed. She says now no one has to know about Lola being his daughter, and he agrees. Serena comes up, and announces that Lola is here and they can now be one big happy family. Lily brings everyone to the table.
Back at the reception, Dan gives a speech but is quickly interrupted by Blair. She announces an endowment to the Young Lions fund to help with children's literacy. She insists on remaining anonymous and tries to raise a toast. At the VDW's, the family has sat down to dinner. Lily begins talking about sharing, and eventually reveals that she knows that Carol and William had an affair. Serena tries to brush it off, saying that the reporter has seen enough drama for the night. Carol demands to know why William told Lily, and he says he didn't tell her. Lola says if she didn't want her to know he was her father, she shouldn't have tried to blackmail him. Lily then brings up the hiring of Ivy, and Carol announces that since she got her money, she's leaving. Before she can, Lily calls two police officers from the back. Lily says she's being arrested for fraud, and Carol says that Ivy was the one who committed fraud, not her. Lily says that Carol is the one who put her up to it, so technically she's the mastermind behind the whole scheme. Carol insists that Ivy would never admit being a part of the scheme because she would incriminate herself, but Lily calls out Ivy, who was also waiting in the back. Ivy tells Carol that she's already given her statement and that in exchange for ratting Carol out, she got off of all charges. The cops arrest Carol, but Lola is angry because her mother's arrest hurts her too. Lily explains that Carol needs to pay for what she did and they should have done this months ago. Lola goes to leave, but William asks to take her home. Serena sees, and jealousy asks if he's going to walk her down the aisle too and leaves.
At the cocktail reception, Dan tries to leave but is stopped by Blair. He asks if she really felt the need to steal the spotlight from him because of the highbrow list, and she says that she's sick of being behind the scenes in a relationship, like she was with Louis and Chuck. Dan tells her she's too focused on what other people see and think of her and leaves. At Diana's hotel, she asks Nate if he wants to resume their relationship. He tells her they can go get a drink and talk about it, and she goes into the bathroom to get dressed. While she's gone, Nate hops out of bed, takes the planner, makes up a lie about Chuck wondering where he is, and quickly leaves. Outside the VDW building, William stops Serena. He apologizes for not being truthful and for cheating on Lily, and she says she's angry that he lied to protect Lola. She says all she ever wanted was a father and all he did was avoid her, and that she can't watch him rush to help Lola now that he found out he's her father. She finishes by saying he broke Lily's heart and now he's broken hers, and walks away. Meanwhile, Rufus goes to see Lily at the penthouse. He tells her he knows she had a dinner and had Carol arrested. Lily says that Carol hurt the family too bad to get away with it. Rufus says he thought they had grown together but if this is who Lily wants to be, he doesn't want any part of it. She says he won't be able to find another UES wife to treat him as well as she does, and he says she just made his choice for them to spend some time apart easier and leaves.
At The Empire, Nate arrives home and Chuck announces he wants to have a relationship with Diana after all. Nate says that before he does, he needs to see an email Elizabeth Fisher sent him earlier that day. Attached in the email is a picture of a very pregnant Elizabeth right before Chuck was born. Chuck questions the fact that Diana said Elizabeth couldn't get pregnant, and Nate replies that Diana probably lied to him and that Jack probably put her up to it. Chuck asks what Jack has to do with anything, and Nate explains that he's the one funding Diana and could have paid her to tell Chuck anything. However, Chuck says things don't add up because Elizabeth denied being his blood donor. At the loft, Blair goes to see Dan. She says he was right, and that the problem isn't his success but her lack of it. She says she's ready to be found and asks him to help. He replies that the real Blair Waldorf is closer than she thinks. At the jail, Carol signs power of attorney over to William and he promises to take care of Lola and hire her the best attorneys he can. At the VDW's Lily writes Ivy a check for one million dollars for helping her take Carol down. Ivy offers to tear up the check to get a place back in Lily's heart, but Lily sends her away. In the elevator, Ivy tears the check up anyway. Lily receives a phone call from William, who says he'll sign over Carol's half of the estate to Lily when he gets to the apartment. He also reminds Lily of her promise to take care of Lola, and Lily skeptically says she remembers. William doesn't believe her and heads to the airport instead of going to see her.
At the Waldorf's, Lola goes to see Serena. She asks for her help in taking Lily down. Serena replies that she never stood a chance as exposing her as Gossip Girl, and she's not interested in being her sister. She tells her to stay away from her and her family and goes to show her out. On her way out of Serena's room, she sees the note Georgina wrote her with the Gossip Girl site passwords and takes it. At The Empire, Chuck explains to Nate that the only thing Diana and Elizabeth have in common is Jack. He tells Nate to look at the tattoo on the man in the photo's arm again, and he produces a photo of himself and Jack on a beach and Jack has the same tattoo. He says that the real question is not who's his mom but who's his dad.. and that he thinks Jack is his father.
- 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
- Kaylee DeFer as Ivy Dickens
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
Recurring Cast/Guest Stars
- William Baldwin as William van der Woodsen
- Elizabeth Hurley as Diana Payne
- Sheila Kelley as Carol Rhodes
- Ella Rae Peck as Lola Rhodes
- Kevin Stapleton as Andrew Tyler
- Zuzanna Szadkowski as Dorota Kishlovsky
- David Patrick Columbia as Himself
- Deborah Eisenberg as Herself
- Body Knows Best by Anya Marina
- Home by Foxes
- End of the Line by Sleigh Bells
- Black Magic by Magic Wands
- Nothing Happened by Paulie Pesh
Serena (to Ivy): It's not my mom's fault the truth finally came out so why don't you leave us alone before we head into one of these offices and file a restraining order against you.
Blair (to Dorota): Don't you know me at all? I love reading bad things about my friends. It's the only thing that makes me feel better about myself.
Blair: And of course, that is the shoe Louis brought back to me from Paris in the beginning of our storybook romance.
Representative: Which ended more famously than it began, didn't it?
Dorota: He was a representative from FIT. Like similar word but spelled s-
Blair: A book can only be read by people who know how to read it. Otherwise it is nothing more than a paperweight or a doorstop.
Lily: Us Van Der Woodsen's share more than you could possibly imagine.
Carol: Yeah, like when you used to steal my leg warmers when we were teenagers.
Lily: Yes, just like that. Or when you stole my husband and decided to have a baby with him behind my back.
Serena (to Lola): So please, just stay away from me and my family, okay, sis?
- Simon & Schuster - Dan's publisher for Inside.
- Twitter - Blair tells Dan he won't be a trending topic on the social networking website if he picks bad topics to discuss.
- New York Magazine - The magazine lists Blair as lowbrow and Dan as highbrow.
- Kim Kardashian - Blair is considered lowbrow for being married for less time than the reality TV star.
- Lincoln Restaurant - Serena receives an email that that's where Lola is.
- FIT - Blair invites a representative from the fashion school to cover her accessory collection.
- Daphne Guinness - Blair's accessory exhibit story was crushed by a preexisting one with the celebutante.
- Young Lion Fiction Award - Dan is nominated for the award at the New York Public Library.
- Gwyneth Paltrow, Victoria Beckham, Mayor Bloomberg - All despicable highbrow people Blair aspires to be in the likes of.
- Ellie Saab - Blair wears a dress of her's to Dan's cocktail reception.
- New York Social Diary - Lily invites a reporter from the organization to a dinner party.
- Hemingway - Dan references the writer in his speech.
- W Magazine - Dan references the internship him and Blair had there.
- JFK - William goes to the airport instead of Lily's.