Riding Town Cars With Boys is the 10th episode of the fifth season and 97th overall.
Apologies have been made and the security breach fixed, but two weeks later and still not one tip. Apparently no one can hold a grudge like an Upper East Sider and no one can lie like one either.
Serena and Lily prepare 'Charlie' for her first debutante ball to welcome her into New York Society. Max will do anything to prove to everyone that she's a fraud. Serena is jealous of Dan's feelings towards Blair and takes matters into her own hands. Blair and Chuck declare their love for each other, but a shocking event will change their lives forever.
The episode begins with Ivy, still pretending to be Charlie, cutting up her driver's license with the name Ivy Dickens on it and then joining Serena, Dan, Lily, and Rufus for breakfast. Serena makes a toast to Charlie and Lily, the former to congratulate her on her debut and the latter for wanting to have one last ball. Lily says that even though Carol made a mockery of her own debut it doesn't mean Charlie should miss the experience herself. Rufus explains that Carol invited Karen Finley to go in her place and when Carol's name was called, Karen came out in chocolate and a pillbox hat. Lily mentions how they were banned from The Plaza for awhile after. Charlie thanks Lily for not only throwing the party, but for paying for her to spend the day at The Plaza Spa. She apologizes once again for the Max debacle and Lily assures her that it wasn't her fault. Charlie also announces that with Diana's departure, Nate offered her her old job back at The Spectator. Rufus then talks about how Inside is doing so well that Simon & Schuster is giving it a second printing. Dan replies that they also want him to write an afterword, and he doesn't know what to say. At the same time, Dan and Serena are fighting and they exchange insults: Dan about Max and Serena killing his movie deal, and Serena about Dan's portrayal of their friends in his book. Lily and Rufus tell them to stop fighting and work it out.
Meanwhile, Blair and Louis are having problems and have't been photographed together in weeks. Chuck is reading an article on their lack of pictures when he overhears Nate cancel a meeting with Mayor Bloomberg. Chuck notices that a week ago Nate couldn't get his office to pay attention and now he's cancelling on them. Nate says that ever since he published the article on staying independent from his family, he's been getting a lot of attention. Chuck replies how that means there are plus sides from going against family, but Nate tells him that William was so pleased he invited Nate to be his guest at Camp Allen that weekend. Chuck excitedly talks about how the legendary camp is filled with the Warren Buffet's of the world, and how they're corporate titans by day and serious debauchery at night. Nate asks why Chuck is reading a rival newspaper, when he sees the article on Blair and Louis' deteriorating relationship. Chuck says that it's probably not true and just another tabloid rumor, but Nate encourages him to call her anyway. Chuck sadly replies that Louis is the father of her baby and there's no way Blair would walk away from that.
Meanwhile at the Waldorf penthouse, Blair's pregnancy is causing her fingers to swell and her engagement ring no longer fits. Dorota tells her that it's normal, but Blair is concerned the paparazzi will take the ring absence to have a deeper meaning. Dorota says that maybe it does, since Louis has been back in New York for a week and Blair still hasn't seen him yet. Blair informs her that she will see Louis when she figures out what to do. Countering Blair, Dorota reminds her that Chuck told her that to make Louis a good man again, she has to reassure him he won't lose her. Blair confesses that she isn't sure she can honestly promise Louis she will never leave him. Dorota asks what is stopping her, since the handsome prince who is also the father of her baby truly loves her and that it's really the thought of Chuck that is stopping her. Blair denies it, saying that while Chuck has changed for the better, her decision has to do with Louis. She tells Dorota that until she decides what to do or her finger swelling goes down, they are not leaving the building. Dorota says that could be a very long time, but Blair replies that they can live off take out for months.
Dan and Serena talk and they apologize. Dan admits he's still unsure of what to write, but Serena says it must be exciting to be able to write about how the book changed him and everyone in their world; since everyone realized where they don't want to be. She mentions how Nate didn't want to be half a person and is now running The Spectator, and how Chuck went from dying alone in the book to going to therapy. She also confesses how she thought working with Jane would change her ending, but she's still making terrible romantic decisions and wishes she had a way to see a different reality where she makes different choices. Dan reminds her that if nothing else, there's always Gossip Girl, who has chronicled her entire life since she was in school. She considers it, before Rufus interrupts and she goes to take Charlie her coat. Dan tells Rufus how Serena pointed out how his book changed everyone except for him. Rufus says it's never too late to change and suggests he deal with his feelings for Blair as a first step and way to move on.
At The Spectator, Tripp comes to see Nate. He asks if they're still on for racquetball that weekend, and Nate tells him how William is taking him to the Allen Retreat and can't make it. Tripp says that the reason he asked Nate is because he turned William down because he coerced Maureen to lie to Tripp. He warns Nate to be careful and leaves.
Dorota presents Blair with a DVD of prenatal yoga and suggests the two get in shape for labor. Blair says no, and instead greets a delivery man. While she signs the delivery slip, he takes out a camera and begins taking pictures. Dorota kicks him out of the apartment and Blair declares that she isn't even safe in her own home. She tells Dorota that she must escape to somewhere the paparazzi wouldn't ever think to look for her. At the same time, Dan calls Blair and she decides to go stay with him in Brooklyn.
At the loft, Dan asks Blair if everything is okay. She replies that everything is horrible because she needs to tell Louis he will never lose her but something is stopping her. Dan says it must be her feelings for Chuck, and Blair again denies it. However, she eventually admits that he is right, but now Chuck has become the man she always wanted him to be and she knows how to make Louis a good man again, so she's trapped and has to choose. She begs Dan to help, and Dan asks to make a pro/con list. She says no at first, but then decides to try. She says that a pro for Chuck is he's finally become a good man, and Dan says as a con that he's slept with everyone in Manhattan. For Louis, he's a prince, but Dan adds he's only the prince of Monaco. She lists how he's the father of her child, and the fact is that that will always have to come first and the only ending to her fairy tale. Dan says it doesn't have to be and is about to confess his feelings, but Blair interprets it as Dan telling her to ask Chuck. She tells him to get some food while she calls.
When Charlie gets to The Plaza, she receives a call from Max. He reminds her that he is not leaving until he gets his money. She says she offered him money that he turned down. He says that five thousand dollars won't get him very far and demands the full amount or he will tell anyone who will listen his story. She blows him off and when she hangs up, he sees the article Nate wrote on family.
Serena has decided to take Dan up on his advice, and reads through old GG blasts. Rufus asks what she's doing, and she admits that Dan is probably the only good guy (besides Nate) that she dated and that she never got it right before or after him. Rufus tells her how it's interesting to see how their passionate relationship turned into such an endearing friendship. At the same time, Serena gets a blast saying that Blair is hiding out at the loft with Dan. Rufus remarks how since Blair is there, Dan got the ending he wanted.
In Brooklyn, Blair calls Chuck, who is surprised to hear from her. She asks if he could love another man's child. She tells him how she's paralyzed and that Chuck has to help her. He says he can't make the decision for her because she'll be the one who has to live with it. Blair asks him again what the right choice is, and he replies that he can't imagine it would be a mistake to marry the father of her child. Blair hangs up in tears.
Nate confronts William at The Spectator and asks if the fake affair story was his idea or Maureen's, and William admits it was his idea because he wanted to help Tripp and was planning on telling Nate. William also confesses to Nate that Diana hired him because he asked her to. Angry, Nate says that the only reason he agreed to work for her was because he didn't want his family's help and wanted to prove himself. William replies that he did, and figured Nate would enjoy journalism and that he wanted to control the press on Tripp. He admits to Nate that the family article he wrote showed that Nate, not Tripp, is the one who has what it takes to lead the Van Der Bilt family in the direction of continual leadership. When William leaves, he mentions how Tripp is afraid of losing the upcoming election, is becoming desperate, and probably told Nate about Maureen because he was jealous about Nate going to Camp Allen. Nate, realizing Tripp lied to him, asks William if he ever asked Tripp to go to Camp Allen, and he says no. Outside Nate's office, Max is waiting to see him. Nate refuses to hear him out, and Max leaves.
On his way back to the loft, Dan gets a call from Serena. She tells him that even though Blair and Louis are having problems, they're still engaged and Blair still has unresolved feelings for Chuck. She warns him not to tell Blair how he feels, claiming she has Blair's best interests at heart, and revealing how he feels won't change his ending, it will only mess with hers. Dan replies that it isn't Serena's choice or ending and tells her to stay out of it. At that moment, Serena sees Louis enter the Waldorf's foyer and tells Dan that she's going to help someone else get their ending. They hang up.
Charlie goes to see Nate at his office to say hi, and he tells her Max came by. He tells her how he turned him down, but she needs to be careful. He admits to being conflicted over his success, and she reassures him that even though William brought him here, he did all the work to succeed.
At The Empire, Lily is using Chuck's suite to help set up for the party. She tells him that as Blair's wedding approaches, she's worried for him and his feelings. Chuck insists he's fine, but Lily reminds him that she cares about him and will always be there for him. Chuck thanks her, but says she has no idea what she would take on. She replies that Chuck doesn't scare her and while he is only her son by marriage, she loves him as her own son. The conversation with Lily leaves Chuck reconsidering the question Blair asked him.
Louis tells Serena how he's going crazy from not hearing from Blair. Serena offers to help, and Louis is confused as to why Serena would want to help him, but Serena insists that he is the only one who can make all of Blair's dreams come true. She makes Louis promise not to scheme anymore before telling him where Blair is. At the loft, Blair vaguely recaps her conversation with Chuck and that Louis is the answer. Dan congratulates and hugs her. He asks her what she really wants, and she answers that she wants to be happy but doesn't know how to be anymore. Dan replies that he knows what will make her happy.
William confronts Tripp about telling Nate. Tripp angrily tells William he isn't going to throw his whole career away because William suddenly decided Nate was the future of the family. Tripp begs William to reconsider, saying he could save his career. William stands firm on his decision, and informs him that Nate is coming with him and he needs to get onboard with the future. When William leaves, Max, overhearing the conversation, tells Tripp they can help each other because they're both sick of being pushed around by people.
Louis tries to get into the loft when Chuck shows up. He is able to retrieve Dan's spare key, since Dan once told him where it was, and the two walk into an empty apartment. Meanwhile, Dan has brought Blair to a secret room at Charlie's party. He reassures her that the paparazzi have no idea where she is and tells her to trust him.
Outside the party, Max runs into Nate. He demands to know what Max is doing there, and Max again threatens to reveal her story to reporters. Nate replies that he'll make sure no one lets him in and goes inside. At the same time, Charlie is having a lot of fun at her party until Nate tells her that Max is trying to sell the story. She blows it off, but Nate tells her that a story is a story and can take on a life of it's own. Serena walks up, looking for either Blair or Dan, and she, Charlie, and Nate see Dan lead Chuck into a back room. Serena asks what he's doing, and Nate says it looks like he's helping Blair and Chuck finally be together. Nate mentions to Charlie that he hopes the paparazzi don't find out Blair is here, or they could ruin the party by trying to get a photo. Charlie asks if they really could ruin the party, and Nate says yes before going to warn security about Max. She sends a tip to Gossip Girl about Blair being there. Inside, Chuck tells Blair that he had it wrong, that just because Louis is the father, that doesn't mean Blair needs to pick him. She asks what he means, and Chuck replies that he will love her baby as much as he loves her and that it would have been selfish to break up her family. At that moment, Blair receives a blast saying that she's at the party with Chuck. The two make a plan to leave together, along with Nate, to leave via the garage. When Lily is giving a speech about Charlie, she notices Chuck, Blair, and Nate leaving and begins to panic. Blair and Chuck leave in one car, and Nate leaves in a different one.
Serena catches up with Dan at the bar and asks if he's okay. She apologizes for coming down so hard on him earlier, and Dan admits he was about to tell her how he felt but was glad he didn't. He admits that the answer to his afterword, was that helping Blair and Chuck be together was the right thing to do all along and that's how he can give himself a new ending. Serena tells him that he's one of the good ones before he leaves. Max calls Charlie and tells her that he got some money and is heading back to Portland. He reminds her that when he leaves, she is trapped in this lie forever. She says she couldn't be happier and she worked hard to be there. Max says that it will get old eventually, and she says it's more than a role, that this is her life and family now. He asks how their love can be real when she's a total fake. She hangs up.
In the car, Nate notices how the paparazzi are aggressively chasing Blair and Chuck's car. Meanwhile, Blair and Chuck confess their love for each other and they decide to spend the rest of their lives together in New York. Nate gets a call from William, and says he's on his way to the airport. Confused, the driver says he thought he was taking Nate back to the Upper East Side. Nate corrects him and they're about to turn around when Nate sees Blair and Chuck's car crash into a wall.
At the hospital, Nate recounts the whole situation to Dan and Serena. He says he stayed with them until the ambulance arrived and the EMT he spoke to said it's pretty bad. Lily calls Eleanor in Paris, and she tells everyone that the Waldorf's are coming in on the next flight. Charlie arrives and asks if they're okay, and Lily goes to look for an update. Serena blames Gossip Girl, saying that the accident is the culmination of years of damage caused by her. She says she wants to take her down, and Nate agrees and offers to use The Spectator to do it. Rufus sees Charlie crying and asks if she's okay. She says it's all her fault and reveals to Rufus she sent the blast to protect herself. She explains that Max showed up and was trying to sell her story. Rufus asks why that's a problem, since Max is a fraud. Charlie replies that she's the fraud. Lily comes back and says Blair is awake and responsive, but breaks down when asked about Chuck. Charlie calls Carol and tells her that she's leaving New York that night and not coming back.
Diana is in a car when she receives a call from Jack. He tells her about Chuck's accident, and she asks how bad. He says he wouldn't take the risk if it wasn't bad, and she agrees to get on the next flight to meet him at the hospital.
- Blake Lively as Serena van der Woodsen
- Leighton Meester as Blair Waldorf
- Penn Badgley as Dan Humphrey
- Chase Crawford as Nate Archibald
- Ed Westwick as Chuck Bass
- Kaylee DeFer as Ivy Dickens
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Zuzanna Szadkowski as Dorota Kishlovsky
- Hugo Becker as Louis Grimaldi
- Elizabeth Hurley as Diana Payne
- James Naughton as William van der Bilt
- Brian J. Smith as Max Harding
- Aaron Tveit as Tripp van der Bilt
- Heartlines by Florence + The Machine
- Anemone by The Joy Formidable
- Arsonist Blues by Patrick Joseph
- You Could Never Be Mine by JoAnna James
- Mirage by Ladytron
- Ace of Hz by Ladytron
- Young Free by Lover Lover
Lily (on Max): That young man had a lot of problems.
Dan: No wonder Serena was so into him.
Dorota: Say like magic spell. Bibbiddi-Bobbidi-Boo I will never leave you. Poof.
Blair (to Dorota): The only downward dog I want to see you doing is cleaning the dust from under that couch.
Dorota: Go to Dorota's in Queens!
Blair: Princesses don't go to Queens.
Dorota: Need to marry Louis to be princess.
Dan (on Blair and Chuck): You two have some strange forcefield effect on each other. Physicists should study it.
Blair: It seems as you've found your way I've lost mine.
Chuck: I didn't think Blair Waldorf could get lost.
Blair: Neither did I, but I'm so lost I wound up in Brooklyn.
Lily: I'm sorry to inform you that my love for you is unconditional.
Chuck: The idea of unconditional love is as quaint as The Tooth Fairy or environmentally friendly dry cleaning.
Lily: Not when you're a parent. Look, you might only be my son by marriage, Charles, but I've always loved you as my own. And I hope you get the opportunity to feel that love for someone someday.
Blair (to Dan): You have brought me to watch a human sacrifice. Or an episode of The Bachelor. Either way, I am not happy.
Nate (to Blair and Chuck): Took you long enough. And I'm not talking about the walk from the lobby to here.
Max (on the VDW's acceptance of Ivy as Charlie): How can their love be real when you're a total fake?
Blair: I have to tell Louis face to face that the wedding is off... he deserves at least that.
Chuck: Are you sure you want to do this? A prince, a fairy tale wedding, this is all you ever wanted.
Blair: No... you're all I ever wanted. I love you. I love every part of you. I-I couldn't tell Louis that he wouldn't ever lose me because it wasn't true. You're the one I never want to leave.
- The episode title is based off the movie Riding in Cars with Boys.
- Karen Finley - Rufus and Lily talk about how Carol hired her to go in her place at her Cotillion.
- The Plaza - Lily mentions how they were banned from The Plaza for years after Carol's antics.
- Simon & Schuster - Rufus talks about the publisher giving Dan's book Inside a second printing.
- Mayor Bloomberg - Nate cancels a meeting with the Mayor of New York.
- Warren Buffet - Chuck says his name in passing as he talks with Nate about Camp Allen.
- Jo Malone - Blair brings Jo Malone candles to Dan's loft.
- Howard Hughes - Dan sarcastically compares Blair to the recluse.
- The Tooth Fairy - Chuck compares unconditional love to the fictional idea.
- Women's Wear Daily - A reporter asks Charlie who her dress is by to put in the article he's writing about the party.
- Badgley Mischka - Charlie wears a dress of the designer's to her party.
- The Bachelor - Blair sarcastically references the TV show to Dan.
Food and Drink
- Breakfast - Rufus prepares a breakfast of waffles, fruit, and champagne.
- Orange Juice - Nate drinks a glass of orange juice at The Empire