How To Succeed in Bassness is the 7th episode of the third season and the 50th overall.
All Hallow's Eve. The one day of the year it's socially acceptable to play dress up. The only question is who do you want to be? There are costumes to make men feel like boys again, or turn little girls into queens. -Gossip Girl
Chuck is preparing for his new club opening and enlists Serena's help, but Blair begins to feel left out. Jenny, the new Queen at Constance, struggles between proving herself and her friendship with Eric, and Dan feels inferior after watching one of Olivia's movies. Meanwhile, Lily tries to respect Rufus' Halloween traditions.
The episode begins with Rufus carving and painting pumpkins for Halloween and Jenny and Lily going through Jenny's closet. Lily wants to get rid of Jenny's old clothes, including one of the dresses she made, but Jenny insists that all of her clothes fit her perfectly and wants to keep them. At The Empire, Chuck tells Blair how the hotel is doing in terms of bookings. Blair says that if he opens the club, it will bring in business and make bookings go up. She suggests an 80s themed party but Chuck shoots down the idea. Blair, suspicious that Chuck is still angry over her lying to him to get the NYU freshman toast (in Enough About Eve), tells him that she apologized and they should move on. He apologizes, and says he's been on edge because of the pressure to prove himself as independent from Bart. He explains that he needs to do things his way and leaves to meet with his accountant. When he's gone, Blair calls a party planner to plan the opening of the club.
At the loft, Nate has brought Dan the Endless Knights trilogy starring Olivia. He tells Dan about how Patrick Roberts, who plays her boyfriend in the movies, was actually her boyfriend in real life. He warns him about comparing himself to what happens in the movie to doing it with her in real life. Dan seems unfazed, until he gets a Gossip Girl blast with a picture of Olivia getting some condoms. At KC's office, Serena finds an annoyed KC over the photo of Olivia. She's annoyed because Serena didn't break up Olivia and Dan like she was asked to. KC explains that Olivia needs to be with Patrick, because otherwise he's headed for a serious career stall and becoming irrelevant. She instructs Serena again to break the two up, or else she'll be stuck running pointless errands for the rest of her life.
On the way to school, Eric and Jenny discuss Halloween. Jenny tells him they have to find a party or else risk handing out candy with Rufus, when they run into her minions. Eric goes off to find Jonathan and Jenny begins bossing her minions around. When they leave, she sees the two sitting on her spot at The Met steps. She tells them to move, not wanting to risk looking weak to her minions, and they do. As they walk off, Jonathan tells Eric that she's changing. Eric defends Jenny, saying it's only a mask for school and Jonathan replies that the mask is becoming her face. Back at the loft, Nate and Dan are watching the Endless Knights trilogy. Dan watches one of the sex scenes and begins to get uncomfortable. Nate asks if he's okay, and Dan tries to play it cool when Olivia calls. He pretends to be sick to buy some time to finish the films and think things over.
Blair goes to see Serena at KCs office. She tells her that she already hired a party planner, but Serena is confused since Chuck wanted to wait until after the holidays to open the club. Blair is confident her plan will work, until Chuck calls and asks for Serena's help in conducting the club opening. He tells her he wants to open the next day on Halloween and that he doesn't want Blair anywhere near the planning. Blair, overhearing the conversation on speakerphone, is shocked. Serena says she guesses Chuck hasn't forgiven her.
The next day, Chuck is setting up for the opening along when Nate drops by to see the progress. He compliments how Chuck is preparing for the party but asks where Blair is. Chuck explains that while they aren't fighting, he isn't exactly in a trusting position when it comes to her. Meanwhile at KC's office, Blair is still mad Chuck asked Serena for help and not her. Serena reasons that it's probably not so much about the kiss so much as Blair breaking his trust. She tells Blair she's trying to make Chuck's party amazing without telling KC and needs to focus on that. Blair decides to leave. At the VDW penthouse, Rufus comes home with a bunch of candy for trick or treaters. Lily, knowing no trick or treaters ever come to their building, tells Rufus they're going to Chuck's party that evening. He refuses, being too excited about handing out candy. Lily tells Vanya, who came up with Rufus, that she can't bear to take away his candy or happiness just yet. On the Met Steps, Jenny's minions are presenting her with accessories for her costume. Jenny is disinterested and annoyed with her minions at their choices. Jonathan and Eric overhear the conversation, and Jonathan is further convinced Jenny has changed. He decides to take a stand and sits on the steps above Jenny. Eric joins him, and Jenny tells the two to move. When they refuse, she gives the order for her minions to pour their yogurt on Eric and they do.
Olivia goes to see Dan at the loft and spots the DVDs on the counter. She asks if she thinks he's a bad actress, and hits the play button and realizes she was watching the sex scenes. He brings up the tabloid rumors and she denies them, saying her and Patrick were only together for publicity. They decide to go to Chuck's club opening and she texts Serena to let her know. Meanwhile, Serena is being confronted about KC for using her client list behind her back. Serena lies and says she only did so to get Patrick and Olivia back together. KC buys the story and agrees to fly Patrick in so the two can go together. At the club, Chuck is desperately trying ti get his liquor license cleared for the party. While contemplating what Bart would do, he receives a call saying the license was cleared. At her dorm, Blair receives a text from Chuck's uncle Jack stating he got the license done.
At the VDW's, Rufus and Lily talk about their trick or treaters. Lily admits that they never get any, but Rufus is confident people will come. Eric shows up, and Lily asks why he's home so early. He tells them to ask Jenny and goes to his room. At the NYU dorms, Blair and Dorota are having mani-pedis when Chuck shows up with a surprise for Blair. He apologizes for not letting the earlier incident go and presents her with a dress to wear to the club opening. She begins to feel guilty. In Brooklyn, Dan and Olivia are trying on their costumes when Serena shows up. She proposes Olivia walk the red carpet with Patrick, telling her she can meet up with Dan inside. Olivia agrees, telling Dan it's only for publicity. At the VDW's, Jenny tries to defend herself to Lily. She tells her how Eric sat above her on the steps and that he knew she would have no choice. Lily says that she can still go to Chuck's party but only if Eric still wants to go with her and if her friends apologize when he gets there. She grudgingly agrees. At the club, Chuck, Blair, and Serena are there whenJack's contact drops his name when dropping off the license. Chuck, thinking only Serena knew about the opening, gets upset at her. Serena reveals that Blair also knew, and Blair brushes it off saying it doesn't matter since Chuck has the license now. Angry, Chuck uninvites her from the party and Serena decides to stay with Chuck instead of going with Blair.
At the opening, Nate and Serena are still fighting and exchange insults. Jenny and her minions meet up and she reveals she has a foolproof plan to get Eric back that they won't be caught at. In her dorm, Blair and Dorota are playing a game of chess while Dorota cleans and Blair mans the board. Blair asks her if she thinks she's trustworthy and she says yes, and then sees Blair cheat at the game. Flowers arrives and they assume they come from Chuck. When Blair reads the card, she realizes they're from Jack and instructs Dorota to get her dress ready. At the VDW's, Lily has paid Vanya to bring some kids up to trick or treat so Rufus can have his fun. Inside the party, Blair finds Chuck and sincerely apologizes for everything. He asks her if she found out that Jack's license was a fake and she asked if he was sent condolence flowers too. They have the same plan and they each go off to control it. Meanwhile, Jenny finds Eric inside and they agree not to talk about what happened again. Outside, Jenny's minions follow Jonathan and throw eggs at him. KC introduces Serena to Patrick Roberts when she sees the police arrive. They look over the liquor license and shut the party down. Serena tells Chuck that he might want to talk to the police and save the party and Chuck asks why he would do that when he called them. She asks Blair what's going on, and Blair reveals their plan: once they knew the license was fake, they could either wait for Jack to call the cops or they could do it themselves and garner the press. Serena is upset, as now she has to get her clients out before they're photographed at a police raided party. Blair explains that without the celebrities Serena brought, they would have been buried in the city section of the news and now they'll be front page. Serena asks Blair why she would do that when she knew how important it was for her to prove herself to KC, and Blair replies that just like when Serena chose Chuck earlier, she's doing the same thing.
At the VDW's, Rufus reveals that he figured out Lily hired the kids. Lily apologizes, saying she didn't want him to have to leave all his traditions behind in Brooklyn and the two decide to go adult trick or treating. Back at the party, Olivia confesses to Dan that she and Patrick really did date and when she dumped him, she broke his heart. She didn't want his career to have to stall and that's why she agreed to do it. She tells Dan the only person she wants to kiss is him and Serena arrives and tells the two to kiss before they head out to where cameras are. While they're kissing, Serena pulls the curtain and announces to the paparazzi that Olivia is kissing her real boyfriend, Dan. They ask who Patrick is dating them, and Serena lies and says she is before they kiss for the camera. Blair and Chuck debrief the party and Chuck tells her that online reservations went up 50% due to the party raid. They make up officially. At Olivia's dorm, Dan and Olivia have sex. When Jenny arrives home, she gets a text from her minion Sawyer that the Jonathan plan went as expected. Eric, having heard about what happened from Jonathan, is mad at Jenny. She tells him that everyone gets egged on Halloween and that she can't hesitate in front of her minions or she'll risk a rebellion. Eric bluntly tells her that there is no longer a difference between her home self and school self and that he wants nothing to do with her anywhere. Serena apologizes profusely to KC, who has decides the party was a good thing. She tells Serena she got Patrick more attention than he's had since Olivia dumped him and that as long as she gets her purse back, her job is safe. At the club, Serena goes back to find her purse. Blair invites her to be a part of a secret club that Chuck mentioned as a way to avoid alcohol regulations and she declines, saying she would never work for Blair. She tells Blair that Chuck might forgive her but she doesn't. Back at the VDW's, Jenny decides to go full UES queen and piles stuff from her old life to get rid of.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chace Crawford as Nate Archibald
- Taylor Momsen as Jenny Humphrey
- Ed Westwick as Chuck Bass
- Jessica Szohr as Vanessa Abrams (credit only, as she does not appear in the episode)
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Hilary Duff as Olivia Burke
- Connor Paolo as Eric van der Woodsen
- Zuzanna Szadkowski as Dorota Kishlovsky
- Aaron Schwartz as Vanya
- Matt Doyle as Jonathan Whitney
- Chuck Cooper as Horace Rogers
- Deanna Russo as KC Cunningham
- Simon Miller as Patrick Roberts
- People C'mon by Delta Spirit
- Nike Town by Son of Dave
- Show Stopper by Peaches
- In Transit by Albert Hammond Jr
- Strictly Game by Harlem Shake
- One Night Stand by The Scotland Yard Gospel Choir
- Freshman by Hollywood Holt
- Central Park Breakdown by American Swing Ensemble
Blair (to Chuck): Either make me kiss a girl already or let's move on.
Nate: Seriously, man? Do you not get internet here in Brooklyn? Okay, Patrick Roberts, who plays her vampire costar, was her boyfriend the whole time they were shooting this. All the blogs said they got really into it and started doing it for real. Like sex tape on the cutting room floor real.
Dan: I think the most disturbing part about this is that you've been reading Endless Nights blogs.
Dan: Look at the way she's looking at him. That's love, that's definitely love and lust and, uh, gratitude.
Nate: Dude, it's an orgasm.
Chuck (on his issues with Blair): A fight requires time and energy. It's more of an ongoing detached distrust.
Rufus (on trick or treaters): I told everyone we'll be home and they all seem excited. Except for the guy on 6th who doesn't make eye contact. It's hard to tell what he's feeling.
Dorota: Oh, Mr. Chuck. When you are mad at Miss Blair, Dorota is very tired and has to have the "foot bothering" and never sees Vanya. Or movies.
Dan: Once in fourth grade, I had to miss recess because I purposely broke the rules of grammar.
Blair (to Serena): Remember when you chose Chuck? Now I did too.
Chuck: Blair. You and I both know you'll never be completely trustworthy. I admit it's not my strong suit either, but it keeps things interesting between us.
- The episode title is based off the movie How to Succeed in Business Without Really Trying.
- Travelocity/Holiday Inn - Chuck tells Blair about where The Empire ranks on the website, just below the Holiday Inn.
- Perez Hilton - The celebrity blogger posted about Olivia getting condoms and is mentioned by Gossip Girl.
- Mark Hamill/Star Wars/Harrison Ford - KC compares the actor to a future Patrick Roberts and Serena asks if that's the guy from Star Wars who isn't Harrison Ford.
- James Franco - KC tells Serena to deliver his underwear.
- Octo-Babies - Jenny tells Eric they have to find Halloween plans or else Rufus will make them dress up as the babies and hand out candy.
- The Real Housewives of New Jersey - Jenny threatens to make her new minions go as the reality TV show cast unless they do what she says.
- Invasion of the Body Snatchers - Jonathan compares Jenny and her two faced personality to the horror movie.
- Last of the Mohicans - Jenny compares the headdress one of her minions brought for her to the movie costumes.
- Gaultier - Jenny's costume is from the vintage designer.
- Lady GaGa/Taylor Swift - Two of the costumes on one of the kids Lily hired to trick or treat.
- ABC - Blair says they could have waited for Jack to call the press or they could.
- TMZ - Serena worries a TMZ video will be shot of her clients leaving the police raid party.
- Bruce Jenner - Olivia mentions Patrick starred in a biopic on the Olympian.
- SoHo House - Blair asks Serena to be a part of a secret club and compares it to the SoHo House.
- Lizzie Grubman - Blair calls KC a Lizzie Grubman wannabe.