The Dark Night is the 3rd episode of the second season and the 21st overall.
In these last hazy days of summer, a few simple tips to beat the heat: one, drink plenty of fluids. Two, stay out of the sun. Three, limit all physical activity - that is, within reason.
Blair questions the lack of passion in her relationship with Marcus, while at the same time Chuck appears to have lost his passion for every woman other than Blair. Meanwhile, Nate struggles between his feelings for Vanessa and his complicated relationship with Catherine. Jenny risks losing her internship when Eleanor catches her crossing the line. Stuck in an elevator due to a blackout, Dan and Serena talk about their relationship and land on a surprising decision.
The episode begins with Chuck day drinking, Jenny working, and Dan and Serena making out in the streets. Meanwhile at the Waldorf's, Blair tries to seduce Marcus into finally consummating their relationship. However, he shuts her down before things go too far and reasons that he wants the moment they do to be special, then encourages her to finish planning her back to school party. Disappointed, she settles for his explanation. Elsewhere on the street, Jenny is on the phone with Vanessa while on her way back to Eleanor's atelier and giving her advice on what to do with Nate. She tells her to call and ask him out, but Vanessa is skeptical with the idea. She takes her advice and calls him, while he's shopping at Ralph Lauren with Catherine. During their conversation, he asks her out for later and she says yes. However, Catherine overhears a little bit of the phone call and grows suspicious when Nate lies that it was his mother. Meanwhile, Dan and Serena debate telling everyone they're back together. Serena suggests they do so at Blair's party, and Dan eventually succumbs to the idea. When he says yes, she kisses him; but unbeknownst to them, a girl stops to take and send a photo to Gossip Girl. Everyone receives the blast, but no one is very surprised by the news. At the loft, Jenny is over the moon with the news. Rufus finds out, and asks Dan if they've worked out all their issues and Dan lies that they have. Later, Nate and Vanessa take a walk together. They wind up back outside his townhouse and he asks when he can see her again. She suggests the next night, but Nate remembers he has a party to attend with Anne. She then asks about having lunch together and he realizes he has a date with Catherine. Disappointed, Vanessa tells him never mind but he answers that he'll reschedule his plans. However, unbeknownst to them, Catherine is watching them from across the street.
The next day at the Waldorf's, Serena helps Blair prepare for the party. While they plan, she tries to converse about her relationship with Dan. However, Blair isn't interested in talking about it and tells Serena that until the two of them talk about why they broke up in the first place, the relationship is doomed. Offended, Serena leaves just as Blair gets a call from Catherine, who is looking for intel on Vanessa, and Blair gives it to her. At the VDW's, Nate arrives to see Chuck to ask for a loan. Chuck hears him out and then turns him down, citing that he sent the money he would give him to his financial advisor and it's now tied up. Nate tells him not to worry about it, then asks if he's okay. Chuck admits he's been feeling a little off his game but that that should be coming to an end very soon. The building concierge then arrives in the penthouse escorting a woman from Tokyo to see Chuck. At Waldorf Designs', Laurel is panicking about getting everything ready for Eleanor's arrival that day. Jenny finishes dressing the model she's working with, then feels that the look isn't right. She calls Laurel over, who disagrees and says that the dress is fine. She then instructs Jenny to dress and not make commentary and walks away. Elsewhere outside, Dan and Serena are taking a walk. Serena complains about Blair's lack of support due to their not talking about issues. Dan doesn't reply and when Serena steps aside to take a phone call from Lily, he notes that they were saved by the bell. While she's on the phone, Dan is stopped by three young girls who criticize him on getting back together with Serena. When the call is over, she shoos them away; then admits to Dan that maybe they do have some things to discuss. He agrees and they awkwardly make plans to talk before Blair's party.
At the art gallery, Vanessa has coffee with Nate. He then gets a text from Catherine wondering where he is. Vanessa notices that he's distracted and he chalks it up to a lot going on. Blair then enters the gallery and invites Nate to come to her party and to bring Vanessa as a guest. Vanessa excuses herself to accept a delivery and Nate asks Blair what she's really up to. She says that she isn't going to sit back and watch him have an affair with her boyfriend's mother and she's trying to use Vanessa as a distraction. Vanessa then reenters the room and Nate confirms that they'll both be at the party that night. Blair leaves and calls Catherine from outside to inform her that Nate is bringing Vanessa to the party that night. At the VDW's, Chuck sends the woman from Tokyo out and runs into Serena in the kitchen. He admits to her that he hasn't been able to perform sexually for the past week. She suggests that he's not over Blair and he realizes she might be onto something. He then announces he's going to have sex with her just to get himself working again and then congratulates Serena for getting back with Dan. At Waldorf Designs, Jenny gives her honest opinion on Eleanor's dress to the model, including that the dress is trying to hard. However, Eleanor enters the atelier and overhears her commentary. She's shocked at Jenny's bluntness and sends the model home before firing Jenny.
Meanwhile, Nate runs into Marcus while he's on a run. Marcus happens to mention that Catherine is attending the party too and that she has become fast friends with Blair. When Marcus is gone, Nate calls Vanessa and lies over voicemail that he isn't going to Blair's anymore due to family issues. At the loft, Vanessa fills Rufus in on Nate's mysteriousness. Dan then emerges from his room and Vanessa tells him to leave first and that she'll see him there. He leaves and Rufus suggests that Vanessa call Nate and ask what's going on; or pretend she forgot her phone at the gallery and act like she never got his message. At the Waldorf's, Chuck attempts to seduce Blair and almost succeeds. However, she catches on and walks away. At the VDW's, Dan arrives to pick up Serena and they act awkwardly around one another. On their way to the elevator, the lights begin to flicker. Back at the Waldorf's, Nate arrives and confronts Blair about setting Vanessa up. She doesn't deny it and then Catherine appears. She pulls Nate aside and informs him that she doesn't like sharing her toys especially when she paid for them. She takes his hand, which Vanessa witnesses; and then puts together just as the penthouse goes dark. Nate tries to follow Vanessa while Blair tries to calm everyone down. Back at the VDW's, Dan and Serena get stuck in the elevator and at Waldorf Designs', Jenny gets stuck in the dark.
Blair informs everyone that there is a citywide blackout and that they have candles so it will be okay. Meanwhile, Nate finds Marcus trying to talk Vanessa out of leaving during a blackout and he walks her to the dining room. He tries to explain the Catherine situation to her and admits to sleeping with her for money because he had no other option. Vanessa mulls it over then asks him to tell her everything. In the foyer, Catherine asks Blair if she's seen Nate. When Blair says no, Catherine says that she saw him go off with Vanessa. Blair brushes it off, then reminds Catherine that her obsession with Nate is a little cliche. Catherine retorts that she knows Blair is sacrificing one important thing she wants in order to be with Marcus and she will have to be without that forever knowingly. She finishes that Nate makes her feel alive before walking away. Back at the VDW's, Dan uses the elevator phone to call down to the front desk. He learns that there's a citywide blackout and they just have to wait it out. Serena admits that he should have mentioned she was in the elevator with him and Dan calls down again to tell them. At the atelier, Jenny tells Eleanor that she's leaving but Eleanor says she can stay until the lights come back on. She then orders her to make herself useful and hold a flashlight while she works. Jenny offers her opinion on the collar and Eleanor realizes she is absolutely right.
Back at the Waldorf's, Nate finishes his story to Vanessa. She asks him if he wants to be with Catherine and he says that he doesn't, and that he wants to be with her. She encourages him to end it because he is better than what he's doing, then promises to be waiting for him once it's done. Elsewhere, Blair jumps Marcus and tries to coerce him into having sex with her. She tries to kiss him and asks him to make her feel alive. Confused, he asks what she means and she tells him to meet her in her bedroom. However, Chuck overhears this and follows her upstairs. Back in the dining room, Catherine arrives to confront Vanessa. She informs her that she has real feelings for Nate and begins to tell her how much she wants to keep him. Upstairs, Chuck enters Blair's room and in a British accent, asks her to blow out her candle. She does so and they begin to make out.
At Waldorf Designs, Eleanor tells Jenny about her travels during the summer and that she felt like a fat irrelevant cheerleader; and Jenny giving rude opinions about her dresses confirms her status. Jenny apologizes and Eleanor replies that she needed to hear that. Jenny then explains that her first "real" couture dress was designed by Eleanor and it was one of the first things that made her want to become a designer. Back at the VDW's, Dan and Serena begin talking about their relationship. Dan tries to escape through a vent in the ceiling but falls to the floor. Serena says she forgives him for Georgina and he says he forgives her too. She realizes that they keep having the same fight over classism over and over but it never changes anything. Back at the Waldorf's, Nate goes looking for Vanessa but finds Catherine waiting for him instead as the lights come back on. Upstairs, Marcus walks in on Blair and Chuck. She runs over to him and tries to explain that she thought it was him. He ignores her and then punches Chuck before walking out of the room. She follows and on the staircase, he demands to know if she really didn't know it was Chuck. Blair hesitates for a moment before admitting she knew it was him. Marcus accuses her of only wanting his title but Blair insists she wants him not to treat her like a delicate flower and to show her he wants her. He kisses her as Chuck and everyone watches. Meanwhile, Nate finds Vanessa, who tells him not to end things because Catherine really wants him. He tries to stop her but she says she's out for good before leaving the party. Afterwards, Catherine comes over to him and tells him they have a date the next day.
Back at the atelier, Rufus and a woman named Claire enter to find Jenny. She realizes Rufus was on a date and they introduce themselves. Eleanor asks what's going on and Jenny introduces her to Rufus and Claire. Rufus asks if she can come with them and Jenny says she's done. Eleanor interrupts and says she can't leave yet because they're still working, and Jenny reminds her that she was fired. Eleanor replies that she shouldn't be so dramatic and asks Rufus and Claire to bring them sandwiches and coffee. At the VDW's, Dan and Serena arrive back in the apartment and agree that once they go home that night, the relationship is over. She kisses him one last time and steps out. He starts to say he still loves her but she stops him and says she does to. Once the elevator is gone, she says she loves him to herself. Elsewhere, Chuck tries again with another woman but fails. He realizes he isn't over Blair yet and that's why. In Brooklyn, Vanessa shares Nate's story with Dan; including the part where Catherine threatened to tell the FBI where Nate's dad is hiding if he ever leaves her.
- 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
- 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
- Amanda Setton as Penelope Shafai
- Mädchen Amick as Catherine Beaton
- Patrick Heusinger as Marcus Beaton
- Yin Chang as Nelly Yuki
- Michelle Hurd as Laurel
- Purva Bedi as Claire
- Closer by Ne-Yo
- I Can Feel a Hot One by Manchester Orchestra
- It's a Lot by The 88
- Like Knives by The Fashion
- Lights Out by Santigold
Serena (on her relationship with Dan): Why can't you support me?
Blair: Have you two talked about everything? About all the very real reasons you broke up last year?
Serena: Well, not completely.
Blair: Well, when you do, if you're still together, then I'll be happy for you. Until then I think you're just fooling yourselves.
Blair (over the phone): Duchess, it's me. He's bringing her. And for the record, whatever you're planning with Nate, my bedroom floor is off limits.
Chuck (referring to his penis): I don't have a romantic bone in my body... least of all that one.
Chuck: Have sex with me... just once, that's all I need.
Blair: You are disgusting and I hate you.
Chuck: Then why are you still holding my hand?
Vanessa (to Nate): I didn't sign up for some creepy love triangle with you and someone's mom!
Catherine: Blair, have you seen Nate?
Blair: Um, no, it's a blackout.
Catherine: Is Marcus everything you could possibly hope for?
Blair: Yes, absolutely.
Catherine: Really? There's not one thing that's missing? That one thing you tell yourself you can live without? That you'd happily sacrifice for the rest? Cause I'll tell you what. You're going to sacrifice it every day for the rest of your life. Nate makes me feel alive. I'm not gonna give that up.
Eleanor: Why don't you try telling the truth? It's not like I can fire you twice.
Jenny: It looks like a pilgrim at a funeral.
Chuck (while making out): This isn't going to work.
Woman: I thought you said you were better.
Chuck: I am. Just not for you.
- The episode title is based off the movie The Dark Knight.
- Two out of the three girls who talk to Dan in the park are the same girls who appear in The Wrong Goodbye, All the Pretty Sources, and New York, I Love You XOXO to offer their opinions on the main character's decisions.
- Ed Westwick, who plays Chuck, is British so when he speaks in a British accent to Blair, that is his real voice.
- Atonement - Blair mentions a scene from this dramatic english movie to Marcus
- Cinderella - Laurel tells Jenny to act like one of the birds from this disney movie
- Drano - Serena mentions this company which makes products to clear septic blockages in pipes
- Keira Knightley - Marcus calls this famous actress a "trollop" compared to Blair
- Little Lord Fauntleroy - Chuck nicknames Marcus after this fictional lord from children's books
- Madama Butterfly - Chuck mentions this Japanese opera
- Ralph Lauren - Catherine says to Nate,"Ralph Lauren adores you", as she helps him put on a suit made by this high-fashion designer
- Shanghai - A city in China where Lily and Bart are currently staying
- The Mercer Hotel - Catherine booked a room in this upscale hotel