Petty in Pink is the 19th episode of the fourth season and 84th overall.
Diamonds are a girl's best friend, but ask any Upper East Side girl to show you her most prized possession and we bet the box is Vivier, not Cartier. But the truth is, just because the shoe fits, doesn't mean you want to wear it.
Serena becomes suspicious of Dan and Blair spending time together, and has Charlie spy on them to find out why. Blair is ecstatic when Prince Louis Grimaldi comes to New York to find her. Meanwhile, Nate helps Raina find out what happened to her mother, while Chuck’s hopes about his legacy are crushed with the reveal of devastating information from the past. Also, Rufus and Eric try to cheer up Lily by having The Pink Party be held at the penthouse: but the party is not without drama.
The episode begins with a montage of how Blair's shoe from Louis got back to her, and then her dressing to spend the day with him. At the VDW's, Lily is sorting through lots of online purchases trying to find a dress that won't show her house arrest ankle bracelet. Serena, Eric, and Charlie return back from going to pastry shops and Lily asks them to help clean the room to have it ready for her friend's to come over. Serena asks Eric to do it, since she needs to talk to Charlie privately. At the loft, Dan explains to Rufus that he was hired to follow a prince who is visiting undercover. However, he's unsure of whether the piece is right for him to do or not, but Rufus assures him it's a great opportunity. He asks how things are with Vanessa, but Dan says they aren't talking anymore. At the Waldorf's, Blair learns from Louis that no one but he can know he's in the city, and she agrees to make a new plan for the day. After they hang up, Penelope and Jessica arrive and Blair tells them to notes for her since she's not going to class. When she refuses to tell them who she's going on a date with, Penelope texts Gossip Girl to find out.
At the VDW's, Serena and Charlie search the Gossip Girl archives for any evidence Dan and Blair are hanging out, but come up short. Soon after, they see a blast about Blair going on a mystery date and Serena instructs Charlie to follow them. Meanwhile, Louis arrives at a small restaurant and Dan is waiting around outside. Charlie is watching from across the street and calls Serena to report. She sees Dan head inside, then sees Blair arrive and enter. Inside, Blair sees Dan and tells him he has to leave. He refuses, and says it doesn't bother him that she's on a date. However after seeing her with Louis, he leaves; but Charlie doesn't see, so she reports to Serena that Blair is with Dan on a date. She immediately heads down there, and is surprised when she finds Blair with Louis, not with Dan. Blair gives her a brief synopsis on why she is with Louis, and Serena wishes her to have fun. She exits, then tells Charlie she probably got mixed up since she's met so many people. Charlie promises it was Dan, but Serena says not to worry about it. She heads back uptown while Charlie secretly uses the Spotted map to follow Dan. At The Empire, Raina begins her search for her mother with Nate. She shows him her birth certificate, and Nate encourages her to talk to Chuck. When she hears Chuck get up, she goes into Nate's room to call the PI. He follows, and after some snooping, Chuck realizes what she is up to. Meanwhile, Dan calls Vanessa and asks her to meet for coffee to talk. At the VDW's, Anne arrives and tells Lily that they did the gift bags at the party location and she asks to have Vanya send over the food before leaving. Rufus overhears, but Lily promises she is fine. He tells Eric that Lily has underestimated her arrest on her social standing. Back at The Empire, Chuck tells Nate that Raina cannot look for her mother, reasoning that Raina is in the press enough to be easy for her mother to contact. Nate thinks it over, and agrees to talk to her. After Nate leaves the room, Chuck calls Andrew Tyler to find out anything and everything he can about the fire.
At the Waldorf's, Louis tells Blair that he was found out, and his parents are sending a plane to take him home. Louis admits he's there to see her, but his parents don't approve since she's a commoner; and that his minder paid one of her friends to follow them. Blair realizes it was Dan, and instructs Louis to prepare for The Pink Party because she has a solution. She calls Dan and tells him to meet her. He goes, and Charlie follows. After they meet, he explains things to Blair. She offers to let him make it right by pretending to be her boyfriend so that when Louis' handler comes to the party, he can be sure that Blair isn't a romantic prospect. Dan is skeptical, and Blair explains that that they're going to stage a kiss that he can see so Louis can stay. He says they would have to tell Serena, but Blair says they absolutely can't. While they shop, Charlie snaps a photo of them. At the VDW's, Rufus, Eric, and Serena plot to have the party moved over to their penthouse. Eric suggests Serena blackmail the co-chair, who tried to kiss her, but she says no. However, she change her mind when she gets a text from Charlie containing the photo of Dan and Blair. At The Empire, Raina and Nate find out theres a potential match for her mother and tell Chuck they're headed to meet her. Chuck asks if he can come for moral support, and Raina agrees to let him come. At the Waldorf's, Blair tells the specifications of her plan to Dan, then finds out the party was moved to the VDW's. However, she says that the plan is still on no matter what.
At the party, Serena tells Charlie that Blair and Dan will most likely sneak way at some point for a private moment, and tells her to follow and capture the moment to expose them. Downstairs, Blair and Louis arrive and she promises Dan is just a friend. Upstairs, Lily is surprised that they got the party moved but is happy anyway. Rufus and Eric overhear some insults about her and realize maybe they didn't make the right call. Blair excitedly tells Serena that she can't wait for her minions to find out she's dating the prince, but Serena acts aloof towards her and asks if she knew Dan was coming. After they finish their conversation, Charlie wonders if Blair really is with the prince. Serena says that if she is, she won't mind if Charlie flirts with Dan. Meanwhile, Chuck, Nate, and Raina go to a diner in New Jersey. They are waited on by a waitress named Avery Thorpe, the same as her mother, and Raina comes out and asks if she could be her mother. The woman is surprised, and says that it's not possible because she has never had a child. After she leaves, Raina realizes it was a mistake and they head home. Back at the party, Charlie begins to flirt with Dan and Blair drags him away after seeing Lucien, Louis' minder, arrive. Lucien sees Blair head upstairs with Dan, and follows, and so does Charlie. Meanwhile, Anne confronts Lily about blackmailing to have the party moved. Rufus says it was all her idea, but Anne tells Lily that everyone was happy at her downfall and walks away. As Dan and Blair are coming downstairs, a Gossip Girl blast comes in with a video of their kiss. When they reach downstairs, Blair confirms that they're dating to show Lucien, who nods in acceptance. Right after, they go to find Serena to explain. Louis tells Serena that Blair isn't with Dan, she only kissed him to save him from being escorted back to Monaco. Serena says they've been secretly dating for awhile and Blair was just lying to him. At the same time, Lily enters the elevator to leave the apartment.
At The Empire, Chuck tells Nate what Russell told him about the fire; and how Avery Thorpe died in it. He says he's trying to find the truth and then Andrew Tyler arrives. Back at the VDW's, Blair and Dan try to explain the video to Serena. She asks about their other kiss, and neither deny it. Dan excuses himself, and Blair and Serena begin to argue. Serena says that Blair only likes Dan because she did, but Blair says that Serena is just jealous that she is getting attention for once. Downstairs, the police arrive to arrest Lily for violating the terms of her agreement. Lily asks them to end her party, and reasons that she wasn't sure if the perimeter was for the apartment or the building. The police go up with her, and end the party. After the party, Lily thanks Rufus for what he did, then says that she doesn't care if she ever sees those women again and just needs him. At the loft, Charlie arrives to apologize to Dan about filming his kiss with Blair. She explains that Serena had her do it, and that Vanessa told her about the original kiss. Meanwhile, Blair explains the situation to Louis, who decides to believe her. He asks her if she is ready to go public, and they exit his car to the awaiting paparazzi; and kiss while cameras flash. At the Waldorf's, Serena calls her friend from Paris, Jean-Michele, to catch up. At the loft, Vanessa meets Dan for their friend date, and he tells her that they are no longer friends and never will be again. At The Empire, Andrew gives Chuck audio surveillance from the night of the fire; and that on it, Bart is heard arguing with Avery. She goes back inside, the place goes up in flames, and she is never heard from again.
- 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 (Credit only, as she does not appear in the episode)
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Kaylee DeFer as Ivy Dickens
- Connor Paolo as Eric van der Woodsen
- Amanda Setton as Penelope Shafai
- Zuzanna Szadkowski as Dorota Kishlovsky
- Hugo Becker as Louis Grimaldi
- Tika Sumpter as Raina Thorpe
- Francie Swift as Anne Archibald
- Alice Callahan as Jessica Leitenberg
- Kevin Stapleton as Andrew Tyler
- White Nights by Oh Land
- Hands by The Ting Tings
- If You Wanna by The Vaccines
- Safety Dance by The Asteroids Galaxy Tour
- We Are Stars by The Pierces
- Gold Into Lead by Two Hours Traffic
- Kiss Kiss Kiss by Danica
- Noisemaker by Two Hours Traffic
Serena (on Dan and Blair going out of town): That doesn't mean anything. They went to Cornwall, Connecticut to find Juliet because she drugged me and tried to convince everyone I was crazy.
Charlie: Sure, because that happens.
Nate: Single malt for breakfast?
Chuck: Takes the edge off the coke.
Charlie (on her and Louis): I don't understand why you're ignoring each other.
Blair: That's because you're from Florida.
Anne: Oh, please, Lily. At least I was quiet in my humiliation. I didn't blackmail people and force them to come to my home.
Rufus: She had nothing to do with it Anne, it was all my doing.
Lily: I have to say, I'm surprised. I thought we were friends.
Anne: Why? You don't know how to be a friend. You shut me out when I called off my divorce to The Captain. There's not a woman in this room who didn't take some pleasure in your downfall. Myself included. So enjoy the party, Lily, this will be your last. Oh, and you may want to adjust your dress. Your monitor's showing.
Serena: The only appeal Dan ever had to you is that he was mine.
Blair: You would see it that way. Because it's always about you, isn't it? I'm sorry to break it to you but Dan and I have a real connection. We did things like visit the DIA and debate Chabrol vs. Rohmer, things that we could never do with you.
Serena: Yeah, I'm sure you and Dan had a really deep connection. That is until a prince came along.
Dan (to Vanessa): I know that we've been friends since we were little, and we both like pirogies, and my dad really misses you, but just to be clear, so there's no misunderstandings down the road, we are not friends anymore.
- The episode title is based off the movie Pretty in Pink.
- Gossip Girl partnered with the website Gilt for this episode. Lily is shown shopping on the site and has boxes from the company inside her apartment.
- Raina is revealed to be 26; which is significantly older than both Chuck and Nate, who are 20 in the episode.
- This is Francie Swift as Anne Archibald's last appearance in the show.