Bonfire of the Vanity is the 10th episode of the second season and the 28th overall.
Some surprises hit you over the head like a squash racket, and others sneak up on you when you're least expecting it. And sometimes the biggest surprises are the ones you spring on yourself. Scampering about in a slip is one way to shed old skin, but will embracing free love be as easy as flinging of a pair of Fendi flats? Looks like someone's going barefoot in the park.
Blair does not approve of the new man in her mother's life and she makes it her mission to break up the two by any means necessary. Jenny moves in with Agnes as they move forward with their plans for a fashion line. Serena continues to fall for the new guy in her life, Aaron, but she discovers something about him that threatens to end things just as they were getting started. Dan tries to win the trust of Bart in order to expose him to further his writing career but things heat up after Chuck realizes the true reason Dan is spending so much time around his family.
At the loft, Dan tells Rufus that he's surprised how calm he is despite Jenny having moved in with Agnes. Rufus replies that he had lunch with Agnes' mom, who promised to have call every day to make sure she's okay. Dan figures that Rufus is pretending to be okay with it so Jenny chooses to come home on her own; a fact that Rufus confirms. He then says he's off to meet Noah Shapiro, who wrote him a recommendation for Yale after reading the story about Chuck. Rufus sadly replies that he's happy for both him and Jenny. At the Waldorf's, Blair, Serena, Penelope, Hazel, Isabel, and Nelly plan Blair's 18th birthday party. While they plan, Serena keeps texting Aaron. Penelope suggests they make several drinks that night to taste test before deciding on which ones to serve. Blair declines, saying she's meeting Eleanor's new boyfriend that night. She explains that Cyrus was one of Eleanor's attorneys and that after repeatedly asking her out, she finally accepted and was wooed. Penelope asks Serena how Aaron is, and she tells about how he sends her directions to special, beautiful places. He sends her directions to a new place and she leaves to find him. Elsewhere, Jenny and Agnes meet with a potential business manager. He asks what the name of their line is, but the girls argue over what it's really called. Frustrated, Agnes throws a tantrum inside the office and gets them both kicked out. Afterwards, Jenny reminds her that the heat from the fashion show will only last so long so they need to find a new backer soon. Agnes promises to do it the next day, swearing it will work out.
That evening, Blair and Eleanor help Dorota prepare for Cyrus' arrival. While Blair directs Dorota, she sees a short, overweight, and balding man enter the apartment. She assumes it's his driver until he kisses Eleanor. Cautiously, she walks over and Eleanor introduces the two. Cyrus grabs her into a hug while she stiffens up. At the VDW's, Chuck wishes Bart a happy 20th anniversary to Bass Industries. He presents him with a present: season tickets to the New York Rangers; which he picked out because he remembered how Bart told him once he snuck into their games as a kid. Bart brushes it off, saying he doesn't have time for hockey games and that Chuck should know that. Elsewhere, Dan meets with Noah, who is having dinner with James Wolf, a senior editor from New York Magazine. James explains that he loved Dan's piece and he wants him to write an exposé written on Bart; which Dan can get since he's close with the Bass family. James offers to give him another piece to write if he delivers, but Dan is still hesitant to take the deal. Noah encourages him to take it, saying this could open real doors for him in the industry. In Times Square, Serena arrives to find herself being shown on a large screen. Aaron surprises her and says he's shown her the most beautiful places he knows and now he wants to show her. He asks her to model for him and she eagerly accepts before they kiss.
The next day, Blair fills Serena in on the Cyrus disappointment at school. However, Serena replies that she's late to meet Aaron, who's going to photograph her. Blair warns her that the role of being a muse and lover will not work out, but Serena thinks it will. Blair then asks what she should do about Cyrus and Serena suggests she be mature and try to tolerate him. Meanwhile, Dan interviews Bart at his office. On his way out, he asks if he could maybe shadow Bart for a few days a week. Bart says no at first, but changes his mind after Dan mentions how Rufus' world is pretty small and he's looking for something more. He offers to start with two days a week and Dan gratefully accepts. At a cafe, Jenny confronts Agnes for blowing her off all day. However, Agnes is hungover and pretty out of it. She says she'll find a new business manager soon before she hurries off to vomit. While she's gone, Jenny steals Agnes' list of contacts from her bag. She gets the number for the guy they met with the day before and calls him. Back at Bart's office, Bart invites Dan to go to a hockey game with him just as Chuck enters the room. He says that he came to have Bart's schedule cleared so they could go to the game together but he guesses he was too late. At the Waldorf's, Eleanor and Cyrus help Blair choose flowers for her party. Cyrus is dissatisfied with one florist, saying they're too expensive. Blair replies that she likes to choose her own florist but thanks him for his help. Cyrus mentions how Eleanor talked about her love for Cyndi Lauper and Blair explains that they love her, and that they used to reenact her Vibes DVD. He then announces that he bought Eleanor tickets to see her in concert the next night so they'll be gone for Blair's party. Eleanor is over the moon but Blair says she wants Eleanor at her party. Confused, Eleanor replies that Blair never wants her at her party but Blair answers that since she's 18 it's a grown up party. Cyrus offers to return the tickets but Eleanor tells him not to, and that she'll celebrate Blair's birthday with her on her real birthday.
Meanwhile, Jenny meets with Scott Smith, the man from the day before. She explains that she and Agnes split business ties and Scott says he would be delighted to work with Jenny alone. Wanting to get started on the paperwork, he tells her that since she's only fifteen, all papers would need to be signed by a parent. Realizing she's at odds with her parents, Jenny nervously says it won't be a problem. Elsewhere, Serena arrives at Aaron's studio but is confused on how to pose. He chooses to go with a more natural approach and takes photos of her just hanging out. At New York Magazine, Chuck watches Dan meet with Noah Shapiro before walking into the building. He calls an old friend who works there and asks what she knows about Dan. She says she knows nothing other than he's going into a meeting with her boss, then says she'll call him back.
The next morning, Serena arrives at the studio to find Aaron there, setting up a 3D display of the photos he took. She's pleasant surprised and tells him it's beautiful. They kiss and Serena admits she likes being Aaron's muse. However, another girl walks into the room and he introduces them, saying she's there to model for him because he's doing a series. Realizing Blair was right, Serena quickly leaves. At the loft, Dan gets an email from an unknown sender telling him to that they should meet, as he knows a secret about Bart. Dan calls Noah and tells him that he has something good on Bart. At the Waldorf's, Blair asks Eleanor how she could love Cyrus since he's so different from Harold. Eleanor admits that she can trust Cyrus and invites Blair to come with her on her errands. Blair declines and she leaves. Once she's gone, Blair tells Dorota that she needs to find a secret of Cyrus' to expose, which shouldn't be hard to do. Meanwhile, Dan goes to the meeting spot where he finds a middle aged guy waiting for him. The guy says that in 1987, Bart bought a building in Midtown Manhattan to convert to condos but the market crashed and he didn't have enough to complete the project. However, the building suddenly and mysteriously burned down. Bart collected the insurance and went on to build his empire. Dan returns home and tell Rufus that all the facts check out. Dan says that the article could change his life, but Rufus reminds him that it could change the whole Bass family life, including Serena and Lily. Dan continues that he just needs a statement from Bart; which Rufus rephrases as Dan tricking Bart into giving him personal information to exploit. While they talk, Rufus gets a call from Alison, who tells him Jenny asked her to sign the papers. She says she didn't and he thanks her for having his back. He then tells Dan that he needs to find Jenny and that they can talk later. Elsewhere, Blair and Cyrus go to lunch. She asks about his ex wife, and he admits he's only felt love like this once before in his life. He explains that he and his first wife, Alice, loved each other but not passionately and that they married young. He continues that he was drafted in the Vietnam War, where he met and fell for a woman named Kim Li; whom he planned to bring back to America after his tour. While he returned to America to end his marriage with Alice, Kim Li was killed in a surprise attack on her village. He finishes that he knew deep in his heart that he was truly in love with Kim Li and he divorced Alice anyway. Finally, he says he feels true love again with Eleanor and his prayers have been answered.
At the VDW's, Serena calls Aaron to see if he wants to go to the Puppet Theatre in Central Park. He declines, saying he's still with Danielle. He suggests they go the next day and she agrees before hanging up. At the Waldorf's, Eleanor confronts Blair about manipulating Cyrus for information. Blair plays dumb, but Eleanor tells her to stop meddling and scheming despite being an adult. However, Eleanor still says that Cyrus is the best man she's ever met and walks out of the room. On the way out, Blair tells her that Cyrus is just like Harold in the sense that he cheated on his first wife and fell in love with the other person. Shocked, Eleanor walks away. On the street, Agnes gets a call from Scott Smith's office, looking for Jenny. The secretary tells her that the paperwork is ready for J Humphrey Designs and Agnes promises to pass the message along. At Blair's party, Serena admits that she was right about the muse and lover thing. Blair asked what happened and Serena explains about the other girl. At Agnes' apartment, Jenny arrives to find Agnes on her way out with Jenny's dresses. She accuses Jenny of being a thief because she knows she stole her contact list. Jenny asks for her dresses back but Agnes places them in a trash can, douses them in lighter fluid, and sets them on fire. She says that now the dresses belong to nobody and Jenny has until she gets back to get all her stuff out of the apartment.
Back at the party, Serena meets Cyrus. He tells her that he recognizes her from Aaron's studio and she asks how he knows Aaron. Cyrus explains that Aaron is his son, and that he is quite smitten with Serena. Pleased, Serena says she's going to go find him. Eleanor then comes up to Cyrus and demands to know if he cheated on his first wife. When he says yes, she kicks him out of the apartment. She tells Blair that she genuinely thought he was different and that she needs to lie down for awhile. Immediately afterwards, Blair spots Cyndi Lauper making her way into the apartment. She explains that her friend Cyrus bought out her show and asked her to play for the party instead because he's in love with her mother. Blair introduces herself as the birthday girl and tells her to make herself at home. She also introduces Dorota, who is starstruck, and tells her to take over while she goes downstairs. Dorota asks what she's doing and Blair says she got a conscience for her birthday. At the VDW's, Dan arrives to see Bart. He lies that he overheard about the fire while at his office and asks him for an explanation. Bart quietly says that it's out and that he's had the man who died that night's death on his conscience for years. Chuck runs out and tells Bart not to say anything more, as Dan is writing the story for a magazine. Bart turns to Dan and asks how much is it going to cost to keep him quiet. Dan says he doesn't want anything and leaves. Chuck follows him to the elevator and pleads with him not to say anything because it will ruin their family.
Outside the Waldorf's, Blair finds Cyrus trying to find a cab since he sent his driver to dinner. She notes that he threw in the towel quickly and then realizes that he outmaneuvered her by inviting Cyndi Lauper to prey on her emotions. He admits that as a lawyer, he thinks several steps ahead because not everyone can rely on their looks. She says he's a genius for what he did, then warns him to be good to Eleanor or else. She invites him to come upstairs while she tells Eleanor the whole truth about everything. He gives her a hug and they simultaneously admit they're not who the other had in mind. At the VDW's, Dan rereads his story on Chuck and his mother before leaving it at the concierge for Bart along with a note saying he should read it. A butler brings it up to him and he reads it for himself. At Aaron's studio, Serena arrives to find him having a candlelit dinner with Danielle. She goes to leave but he follows her to explain. He tells her that he likes to date several people at once and that while that might not be how it works in high school, she can see other people too. Offended, she walks out. At the loft, Jenny walks in to find Rufus strumming his guitar alone. He says he's happy to have her home and she says she's only coming back if he signs the papers. Rufus refuses to, saying he won't let her get what she wants after hurting so many people. She replies that she'll just have to find another way and leaves the loft. However, she goes downstairs and begins to cry on the street.
The next morning, Jenny wakes up at the art gallery after spending the night there and calls Scott Smith to request a meeting. At the VDW's, Bart apologizes to Chuck and says he never once blamed him for his mother's death. He admits he had no idea he ever felt that way and the only reason he has trouble being close to Chuck is because he reminds him of his late wife, whom he misses dearly. He finishes by saying he wants to know his son and asks if he wants to go to a hockey game. Chuck hesitates, then says he'll clear his calendar. At the loft, Rufus tells Dan that he spoke to Jenny. Dan says she called him and that he killed the story on Bart. Rufus replies that he saved the Bass family, and Dan says that it's time for Rufus to save their's. He encourages him to get Jenny back, even if that means giving her what she wants despite her not deserving it. At Scott Smith's office, she asks what to do if neither of her parents will sign the papers. Scott suggests she get herself emancipated and legally sever all ties with her parents. She thinks it over, then asks what she needs to do. At the Waldorf's, Blair talks on the phone with Serena, who tells her that she ended things with Aaron after finding out he's a casual dater. Serena asks how she's doing with Cyrus, and Blair admits that he isn't that bad and she's going to tolerate him because he makes Eleanor happy. She walks into the dining room to find them eating breakfast together and she hangs up with Serena. Cyrus happily says that they spent all night talking and they mutually decided that he should move in right away. At the VDW's, Aaron arrives to see Serena. She asks why he's there since they broke up, and he reminds her they weren't going out. He admits that he really likes her and wants to pursue a life without all the stuffiness of the Upper East Side; and that he thought she wanted that too. She agrees with him, and says he's right. She then grabs her coat and leaves with him while still in her slip. They go to the park and hang out.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald (Credit only, as he does not appear in the episode)
- 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 (Credit only, as she does not appear in the episode)
- Matthew Settle as Rufus Humphrey
- Margaret Colin as Eleanor Waldorf
- Wallace Shawn as Cyrus Rose
- Zuzanna Szadkowski as Dorota Kishlovsky
- Amanda Setton as Penelope Shafai
- Dreama Walker as Hazel Williams
- Yin Chang as Nelly Yuki
- Nicole Fiscella as Isabel Coates
- Robert John Burke as Bart Bass
- John Patrick Amedori as Aaron Rose
- Willa Holland as Agnes Andrews
- David Patrick Kelly as Noah Shapiro
- Brennan Brown as Scott Smith
- Peter Francis James as James Wolf
- Cyndi Lauper as Herself
- Sex on Fire by Kings of Leon
- Satellites by We Know, Plato!
- Closer by Kings of Leon
- Be Somebody by Kings of Leon
- What Is a Life? by Youth Group
- Echo by Cyndi Lauper
- Manhattan by Alain Whyte
- Shooting War by We Know, Plato!
Blair (on Aaron): Serena, a guy starts out in his blue period and it's all great but it's only a matter of time before he's all into cubism and it's some other girl's eye coming out of her forehead!
Blair: How could you possible love Cyrus? He does all the things you hate. He uses the wrong fork, he slurps his soup, he wears sports socks, he's short, and pushy. He's nothing like Daddy.
Eleanor: Which is precisely why I like him. Harold was lovely in a million ways but he had his secrets. Cyrus is someone I can trust.
Cyrus (to Blair): Your mother is a diamond in an ocean of coal.
Blair: I wanted a Harry Winston choker for my birthday but instead I got a conscience.
Jenny: Hey, Dad. Can I come in?
Rufus: Of course you can, Jenny. This is your home. I'm happy to have you back.
Jenny: I'm not back yet. But I will be if you sign these papers.
Rufus: You mean the papers your mother already refused to sign?
Jenny: She only refused because she didn't want to get in the middle.
Rufus: And here I thought you came to your sense. You don't even have your coat off and you're already using emotional blackmail to get your way.
Jenny: Spin it however you like: I just need your signature.
Rufus: If I sign this paper, it means that everything you've done up to now: this lying, cheating, manipulation... it's all okay.
Jenny: And if you don't sign them, then everything I've done, everything, is all for nothing.
Rufus: I won't put my name on a piece of paper condoning who you've become.
Jenny: Fine. Then I'll just have to find another way.
Bart: I want to apologize, son.
Bart: I never blamed you for your mother's death. I read that short story that uh, Dan Humphrey wrote about you and your mother. I had no idea you felt that way. It's my fault. I know I've had... trouble being close to you, but it's not for the reasons you think. It's just hard because... every time I look at you, I see her.
Chuck: You miss her.
Bart: You have no idea. I've made some terrible mistakes in my life but I don't want to make another. I want to know my son.
- The episode title is based off the movie Bonfire of the Vanities.
- Gossip Girl doesn't have her usual voiceover in the beginning of the episode.
- This episode is the first appearance of Cyrus Rose.
- Dan's email is Daniel_Humphrey@stjudes.org.
- This is the only episode where Bart's character in Dan's story world, Bernie, is mentioned.
- Bart's line "I want to know my son" is repeated by Chuck's mother, Elizabeth Fisher, when she returns in season three.