It-Girl Happened One Night is the 15th episode of the fourth season and the 80th overall.
It's cold out there, but on the Upper East Side, things are heating up because Valentine's Day is around the corner.
As Russell Thorpe is prepared to takeover Bass Industries, Chuck makes one last attempt to save his father's company by throwing a Valentine's Day fundraiser, and tries to cut Lily loose from his company in an attempt to prove his limits. Meanwhile, at W Magazine, a difficult assignment gives Blair the opportunity for a promotion. Elsewhere, Serena struggles with her feelings for Ben despite her family's disapproval. Also, The Captain faces problems due to him being considered a conflict of interest to Russell: but it may work to Chuck's advantage.
The episode begins with Blair getting ready for work while talking to Serena, who is missing having her around. Blair admits she's sitting Valentine's Day out to focus on work, and so is Chuck, but she isn't worried about him really having feelings for Raina. Serena says that she and Ben are sitting it out too, since they just started dating. She suggests they have a friend's Valentine's celebration but Blair doesn't commit in case she has to work. At the VDW's, Raina and Russell arrive to have brunch with Chuck, Lily, and Rufus. Upstairs, Lily warns Chuck not to let his personal feelings for Raina cloud his judgment and he promises not to. At the loft, Dan is looking on how to contact Epperly and Ben is looking for a job. Dan offers to call the catering company he used to work for to help Ben find a job. Ben is grateful, as he didn't want to celebrate Valentine's Day because he was broke, and advises Ben to just go find the person who took over Epperly's job to help him.
At W, Blair is being briefed on how the magazine is planning a new feature where they follow a new It-Girl a month as she navigates Manhattan. Serena is suggested, but Blair proposes they ask Raina instead, and the board agrees to consider her trial period over if she comes through. She calls Serena, and asks her to go to where Raina is, the VDW building, and ask her to talk to Blair about doing it. After some prodding, Serena goes to do it. At the VDW's, Chuck proposes to Russell that he wants to prove Bass Industries' worth with a party the next evening, and that he's sure it will succeed. Russell agrees to put a pin in his plans for the next 36 hours and if it succeeds, they'll talk about the future. Right after, Serena shows up and gives Raina her phone to talk to Blair. While she talks, Serena explains the situation to Chuck. However, he tells her that his feelings for Raina are real and he has something special planned for her. Outside after she leaves, Serena calls Ben and he tells her he got a job. She asks what the job is, and he lies that he's tutoring. After they hang up, she heads into Ralph Lauren. At The Empire, Nate brings Howard over to talk to Chuck. Howard informs him that he was accidentally copied on a report that included how Thorpe plans to break down Bass Industries and who will be buying them, and that a meeting with a buyer was just confirmed an hour ago. He also explains that he did some research on his own and learned that Bass Industries is more profitable kept whole so there's no real reason to slice to up. Nate suggests that maybe Russell's issues with Bart is what is causing the decision. Meanwhile, at Ralph Lauren, Serena confesses to Raina that Blair still has feelings for Chuck and that her following on Valentine's Day will only hurt her. Raina thanks her for the heads up, and agrees to cancel the piece. At W, Dan arrives and is surprised to find Blair is the new Epperly. Dan asks her to forward an article he wrote to Details Magazine, but she refuses. Blair reminds him of his cater waiter past, but he tells her he gave his job to Ben. At that moment, Raina calls to cancel the article. After they hang up, Chuck calls Raina asking if she knows why Russell hates Bart. Raina explains that she doesn't know because she was at Penn at the time, and all she really knows is Lily was dating Russell until she left him for Bart.
At a food truck the next day, Dan and Eric hang out. Eric explains that he hasn't heard from Damien but assumes he was exiled to somewhere far away, and that he also hasn't heard from Jonathan. Dan suggests he invite him to Chuck's party, but Eric replies that he already has plans to help deliver food to sick people. Dan then says he is planning to find Blair at Chuck's party to force her to help him get his article out. At the Waldorf's, Blair comes home from work early to figure out a way to get Raina to recommit when she runs into Serena in the foyer. Serena suggests they can now do the friend's Valentine's Day like she wanted and Blair notices she has a box. She asks who it's from, but Serena says Lily sent it and heads off to call the masseuse. In her haste, she forgets the card and Blair opens it; only to find the box enclosed a gift from Raina thanking her for the advice to cancel the profile. Meanwhile, Chuck goes to see Russell at his office. He explains that he has no loyalty to Lily and only to the Bass name. He offers to get rid of Lily from the company, and calls a member of the board to set up a meeting to discuss firing her. Russell is impressed and tells him to stay on course and he's looking at being taken care of after the sale. At the Waldorf's, Blair tells Serena that she has to work and encourages her to go to Chuck's party. She mentions that Ben is tutoring, and Blair is skeptical but doesn't press about it. At the VDW's, Lily cancels her plans with Rufus to attend the emergency Bass board meeting. Rufus tells her to stand up for herself, and she replies that Chuck had her removed from the board. Back at the Waldorf's, Blair finds the catering company that Ben is working for and calls them to make sure Ben is working Chuck's party.
At the party, Russell congratulates Chuck on the success of the party. Chuck thanks Raina for inspiring him, and she promises that no one will forget the night. Elsewhere, Blair arrives with her team of reporters but sends them away when she sees Dan. He says that he's there to see if she read the article, but she says she has more important things to see and report on. She rejoins her crew and they start to interview Serena. Lily arrives at the party and runs right into Russell. She tells him that whatever he's doing is working and Chuck needs to know. Howard finds Nate and tells him that he's going to quit his job. Meanwhile, Chuck tells Raina that he knows she was supposed to be in Venice but had to cancel and he arranged something special for her. He leads her into an elegantly dressed room, complete with candles and a bed. He tells her that when he cares for someone, he isn't afraid to show it and they kiss. Unbeknownst to them, Dan stumbles into the room and sees them kiss. Lily then comes up and asks if he's seen Chuck. During Serena's interview, Blair asks who her Valentine is. Serena says she likes to keep her private life private, and Blair announces that her Valentine is Ben; who is there working the party. Serena heads over to him and says she thought he was tutoring. Ben says he was embarrassed, and he thinks they've seen enough of each other for the night. Meanwhile, Lily enters Chuck's special room and confronts him. She demands to know why Chuck had her fired, and he explains that she should have explained about Russell. She says it has no influence on her performance at Bass, but Chuck doesn't agree. Shocked at how he's talking to her, Raina leaves the room, followed by Lily. Russell enters and announces to Chuck that words are overrated and now that Lily is gone, he has a clear path to destroy Bass Industries. Chuck threatens to tell Raina what he did, but Russell is confident it won't change her mind about how she perceives Chuck now. Out at the party, Serena confronts Blair about putting Ben on the spot like that. Blair reveals she knows she had Raina drop out, but Serena explains she was genuinely worried Blair would be hurt by her and Chuck. However, Blair insists that Chuck has no real feelings for her and goes off to find him so he can tell her himself. On her way to find him, Dan sees her and decides to follow. Elsewhere, Russell fires Howard, saying that even though he wanted him to expose the email report, he can't have people around that he doesn't trust. On her Chuck hunt, Blair ends up in his room for Raina. She asks Dan what it is, and he explains that he built it for Raina. They hear him coming and hurry behind a curtain. Chuck and Raina reenter the room and he begs for her to forgive him. She tells him that she can't, and she's seen all she's needed to see and leaves. Behind the curtain, Blair starts tearing up as she realizes Chuck really does have feelings for Raina and sits down. Dan sits beside her and takes her hand, but she quickly removes hers.
After the party, Serena returns home and Blair brings in candy for her. She admits that Serena was right about Chuck and Raina being real, and apologizes for ruining her night. Serena says that maybe she should have gone right to her about her concerns instead of behind her back, and they make up. Blair explains that she found some blackmail material and used it to cut the Ben part out of the article. At that moment, Ben texts her and asks if they can meet. She asks Blair if she'll be okay, and then leaves. Blair then receives a text from Dan telling her he's started a new draft on his article, and she calls him to say she forwarded the article he gave her to Vanity Fair; then admits that she read it and liked it. He asks how she's doing knowing Chuck is dating someone else, and she replies that she's about to watch Rosemary's Baby. He decides to watch it with her, and they stay on the line while it plays. At The Empire, Howard tells Nate and Chuck that when he was fired, he had to turn in his access key card and he gave them one to the gym at The Empire. He hands over the card to get into Russell's office, and also a list of all the passwords to get into the computer system. At a bar, Serena meets with Ben. He admits he should have told her about the job, and she apologizes for putting words in his mouth. They agree to hang out and drink beer together. Meanwhile, Blair and Dan discuss commentary on the movie while they watch together. Elsewhere, Eric finishes volunteering and a fellow worker tells him that a cute guy came around asking for him and is waiting around the corner. Eric goes to see, assuming it's Jonathan, and is shocked to find Damien waiting. He says that after Nate and Dan ratted him out, he's under a microscope and unless Eric helps him run his business, he'll tell everyone about Lily's forgery.
- 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 (Credit only, as she does not appear in the episode)
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Connor Paolo as Eric van der Woodsen
- Kevin Zegers as Damien Dalgaard
- Michael Boatman as Russell Thorpe
- Tika Sumpter as Raina Thorpe
- David Call as Ben Donovan
- Sam Robards as Howard 'The Captain' Archibald
- We Turn It Up by Oh Land
- Drinks On The House by Daniel May
- The Speakeasy by Daniel May
- Meyrin Fields by Broken Bells
- At Your Door by Alexi Murdoch
- U + Me = by Dan Black
- Beginners Falafel by Flying Lotus
- You by Wages
- A Giant Transformation by Henry Jackman
- Transfiguration by Henry Jackman
Chuck (to Howard): I think I'll take my advice from someone not interested in grinding an ax across my knuckles. If you don't mind.
Dan (on Epperly being gone): Oh, god, what'd you do to her?
Blair: She's in a better place. She's in Bali doing downward dogs with some British wally named Prat or prat named Wally. In any case, she quit.
Russell (to Chuck): I think you know how much family means to Raina, just as she now knows how little it means to you.
Chuck: You put family before all else, I can't do that. My father was never there for me, my mother abandoned and betrayed me, my uncle is my worst enemy. But maybe your father isn't as perfect as you think.
Raina: What are you saying?
Chuck: He's the reason I went after Lily. He pitted me against her.
Raina: So you're trying to turn me against him?
Raina: Ruin MY relationship? Nothing is sacred to you
Chuck: That's not true. You are sacred to me.
Raina: Until I do something you don't like and you turn on me too.
Serena: You gonna be okay alone?
Blair: Not yet... But I need to start learning to be.
Eric: I've gotten more hugs tonight from strangers than my grandmother has doled out my entire life.
- The episode title is based off the movie It Happened One Night.