Summer, Kind of Wonderful is the 1st episode of the second season and the 19th overall. It is also the season premiere.
Unlike the rest of us, sex, lies, and scandal never take a vacation. Instead, they take the Long Island Expressway and head east to the Hamptons. Some would say summer is their busiest season. Think Park Avenue, but with tennis whites and Bain de Soleil. The players change but the game remains the same.
As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple; to cover up the fact that Nate has been having an affair with an older woman. Blair returns from abroad with a hot guy on her arm, making a very jealous Chuck question his decision to stop pursuing Blair. Meanwhile, Dan has spent the summer assisting a famous author, but finds himself preoccupied with Serena, leading him to take a risk. While interning for Eleanor Waldorf's company, Jenny procures an invite to the much-anticipated Hampton's White Party, with the help of Eric van der Woodsen.
The episode begins with Nate making out with a mysterious, older woman in The Hamptons. She asks if Serena really is okay with covering for them, and he says yes, since she's trying to move on from her break up. The woman then suggests they go to her house to continue, and he agrees. Meanwhile, Chuck is on the beach with three women. While watching them, he receives a Gossip Girl blast saying that Blair is on her way home from Paris. Elsewhere, Serena is also at the beach; alone. Back in New York, Dan is making out with a woman at a reading of Jeremiah Harris, whom Dan is interning with for the summer. When the reading is done, Jeremiah asks if Dan knew he read from his favorite chapter; knowing Dan was busy doing something else. He then asks where the story Dan is supposed to write for his internship is, and Dan tries to make up excuses to cover for the fact it isn't done. He promises to have it done the next day, and Jeremiah sends him home to finish it. At Eleanor's atelier, Jenny tries hard to get the attention of Laurel, Eleanor's head while she's in Paris. She attempts to show her a dress she made for her to wear to the Vitamin Water White Party; but Laurel blows her off, and points out everything wrong with the dress. She then orders Jenny to match up a bunch of buttons and walks away. That night at the loft, Jenny asks how Dan's story is going. She also mentions that she hopes once she reads it, she can understand why he and Serena broke up. He agrees to himself. Back in The Hamptons, Serena finds Chuck getting ready to go somewhere. She asks if he heard Blair was coming, then reminds him that Blair will never forgive him for what he did to her. He retorts that he isn't going to take advice from someone in a fake relationship, and leaves to meet Blair at The Hampton Jitney. However, when the bus arrives, he sees her get off and kiss a guy she clearly came with.
The next day, Blair and Serena sit out together and discuss the summer. Blair is shocked when she learns Serena didn't do anything with anyone all summer. Serena mentions that a lifeguard asked her out but she declined; and Blair tells her that's a perfect rebound so she shouldn't have said no. At that moment, Chuck approaches while on the phone, but he hangs up, and Blair immediately pretends she and Serena were discussing her new boyfriend, James. She brags that he bought her a necklace, and Serena confusedly asks who James is and that she thought Harold gave her the necklace. However, she soon notices Chuck looming and plays along with her. Chuck accuses her of lying, but Blair adamantly denies it. He tells her that she is trying to make him jealous to hurt him the way he hurt her by abandoning her on the tarmac, but she refuses to admit what he did hurt her. She offers to bring James to dinner so they can bond, and he agrees to come. Once he's gone, she asks Serena to go find the lifeguard together and to go to Nate's so she can get something she needs. Meanwhile, Jenny talks to Rufus, who is still on tour. She fills him in on the happenings at the loft, and explains the White Party to him. He remarks that the VDW's would probably be going to an exclusive party like that and she should ask Eric, but she admits that's not a good idea since she said things she shouldn't have the last time they talked. However, he encourages her to keep trying and maybe things will go her way; and she decides to take his advice. Elsewhere, Dan goes to see Jeremiah at his favorite bar, sans the story. He asks for a little more time, but Jeremiah refuses, saying he had enough time and he will not get a letter of recommendation.
In the Hamptons, Eric is taking a walk on the beach when he gets a call from Jenny. He correctly guesses she wants something, and she apologizes for everything that happened between them. After hearing her out, he decides to forgive her and find out what favor she wants. Meanwhile, Serena is about to head out on a date with the lifeguard. Blair wishes her luck, and Serena reminds her to say she's with Nate if anyone asks. Elsewhere, Nate is making out with the same woman from the day before in her guest house. Back at CeCe's house, Blair, Eric, Chuck, James, and CeCe have dinner together. Chuck grills James on facts about Blair, but stops when he notices the heart pin she once gave Nate on his sleeve. He excuses himself, and takes a walk. Blair follows, and he tells her that he knows she gave Nate that pin the first time she said she loved him. She replies that she asked for it back, and he asks if she really does feel the same for James that she did Nate; and she says she does. When she returns to the table, she takes the pin back, claiming it got caught on his sweater. Elsewhere, Nate finishes having sex with the woman, Catherine, and upon seeing her husband is home, she orders him to either get under the bed or go out the window. He chooses to go out the window, still underwear clad, and runs off. He runs into the road, and right into Serena and the lifeguard. Seeing where he came from, and Catherine kissing her husband, she quickly pieces the whole thing together. The next day, Blair admits to Serena that she doesn't even like James; and she only hooked up with him because she knew she couldn't come home alone. She also mentions that now she's planning to dumb James and go to the White Party alone. Meanwhile, Chuck tells Nate that he's going home to avoid seeing Blair with James anymore. Right after, the four run into each other. Serena and Nate pair off for a minute, and he tells her that Catherine dumped him the night before. At the same time, Chuck and Blair argue over which college James goes to. Annoyed, Blair leaves with Serena and Chuck calls Eric to ask him to do some research on who is right.
Back at the loft, Dan fills Rufus in on getting fired by Jeremiah. He admits that he's been avoiding seeing and talking to Serena all summer because he doesn't want to get the feeling that he made a huge mistake breaking up with her. Rufus then advises him to stop running and try to work through his unresolved feelings. Back in the Hamptons, Eric tells Nate and Chuck that he couldn't find a record of James at any big college in the US. Chuck thinks that James is using Blair to gain entry into upper class life and decides to call his PI to investigate deeper. Elsewhere, Blair tries to break up with James, but before she can, receives a text from Chuck that he'll be at the White Party after all. After she sees it, she changes her mind and invites him to go to the party with her instead. Meanwhile, Serena confronts Nate about telling CeCe that they're going to the White Party together. He admits to her that he has feelings for Catherine, and wants to go to see her with her husband. Serena tells him it's a bad idea, but decides to go along with the plan anyway. At the same time, unbeknownst to anyone, Dan arrives in the Hamptons to see Serena.
At the party, Jenny arrives with Eric. Upon walking in, she makes eye contact with Laurel; who is clearly surprised to see her there. Meanwhile, Serena and Nate walk past Catherine and her husband, and upon her seeing them, whispers to Nate to ask him if he's trying to ruin her marriage. At CeCe's house, Dan arrives to find only CeCe at the house. She informs him that Serena is not there, and asks him to help her put a necklace on. After he helps her, she says that she realized that not everyone can be made happy the same way and she knows Serena isn't over him. Then she offers help him get into the White Party. Back at the party, James tries to tell Blair that his feelings for her have deepened, but she isn't listening; as she's too preoccupied with trying to make Chuck jealous. James catches on soon enough and walks away from her. Elsewhere, Laurel asks Jenny how she snuck into the party, considering she probably wouldn't know anyone that would bring her as a plus one. While she's talking, Eric comes up with Tinsley Mortimer; who is very interested in Jenny and her designs. At the same time, Blair asks James if anything is wrong; and he accuses her of using him to make Chuck jealous. He asks if she even likes him, and she says she doesn't because he's kind of boring. He retorts that she and Chuck deserve each other and walks away. Once he's gone, Chuck comes up to Blair; who instantly blames him for making her use James. Chuck says that he didn't make her do anything, she used him because its who she is. Angry, Blair replies that any resemblance to him is something she would hate about herself and walks away. Meanwhile, Catherine is still whispering snide comments to Nate any chance she gets. He admits to Serena that he just wants to make her feel as bad as he does, and Serena says he can. She kisses him deeply, not knowing Dan is watching the whole thing transpire. When the kiss is over, she notices him. He walks away, and she follows, trying her best to explain without really explaining. While they argue, two women approach Dan and throw drinks on him for seeing them both at the same time.
Back inside the party, Catherine pulls Nate aside and asks why he kissed Serena. She then says she can't believe Nate would try and make her jealous in front of her husband and friends; and he asked if it worked. She answers that it completely did and they begin to make out. Meanwhile, Dan and Serena talk. He confesses that he hasn't been able to get her out of his head all summer and that he hoped seeing her would make him realize they did the right thing, but that didn't happen. They kiss, and make plans to leave the party and go to the beach together. On his way out, Dan runs into CeCe; who smiles with approval at him and Serena making up. Elsewhere, Blair finds James and admits that she did use him. However, Chuck is watching and receives a call from his PI; who has new information on James, who tells Blair he wasn't completely honest with her. He confesses that his name isn't James, it's Marcus Beaton, and he's actually a British lord. Chuck notices them talking, and realizes he's probably telling her who he really is. Marcus explains that most women are only interested in him for his title, so he decided to pretend to be a common American to make sure he wasn't being used. Then he says that no one has ever told him he was boring, and he liked it. They both decide to be more honest with each other and take a walk together. Back inside, Laurel tells Jenny she heard Tinsley offered to help her get an internship. Jenny answers that she did, but she turned down the offer because she's learning a lot where she is. Laurel tells her to enjoy her weekend, and finally calls her by the right name.
Outside, Chuck approaches Blair, and admits he should have never abandoned her. He asks her not to leave with Marcus, and she asks him to give her a reason not to go. Eventually, she asks him to tell her he loves her, but he is unable to do so. Afterwards, she leaves with Marcus. Back inside, Catherine slips Nate a note with a meeting time. At the beach, Serena finds Dan, who is waiting for her next to a bonfire. They hold each other while they watch fireworks.
- 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)
- Kelly Rutherford as Lily van der Woodsen (Credit only, as she does not appear in the episode)
- Matthew Settle as Rufus Humphrey
- Connor Paolo as Eric van der Woodsen
- Caroline Lagerfelt as CeCe Rhodes
- Mädchen Amick as Catherine Beaton
- Patrick Heusinger as Marcus Beaton (James)
- Jay McInerney as Jeremiah Harris
- Michelle Hurd as Laurel
- Tinsley Mortimer as Herself
- Reverse of Shade by The Windupdeads
- Buzzing' by Shwayze
- Fell In Love Without You (Acoustic) by Motion City Soundtrack
- Crazy by Jem
- Break It Down by Alana D
- Google Me by Teyana Taylor
- Paparazzi by Lady GaGa
Blair (to Chuck): I wasn't aware robots got jealous. Did they update your software while I was away?
Eric (to Chuck): "How Well Do You Know Blair Waldorf" is kinda boring for those of us who actually know Blair Waldorf.
CeCe: Not to mention transparent.
Chuck: Thank you, Grandma.
CeCe: Why is it when you say that word it sounds like an insult?
Blair: Damn that motherchucker!
Blair: You don't understand. Chuck is a awful person. He does terrible things, he uses people.
James: And you think you're any different.
Dan (to Serena): It can never be a simple answer with you. It can't just be "I kissed Nate." It has to be "I kissed Nate because someone I can't name needed to see it for a reason I can't explain."
Chuck: Look, I should have never abandoned you. I knew I made the wrong decision as soon as your plane took off. I distracted myself all summer, hoping I wouldn't feel it, but I still do.
Chuck: I was scared. Scared that if we spent the whole summer together, just us, that you'd see.
Blair: See what?
Chuck: Me. Please don't leave with him.
Blair: Why? Give me a reason. And "I'm Chuck Bass" doesn't count.
Chuck: Because you don't want to.
Blair: Thats not enough..
Chuck: Because I don't want you to.
Blair: It's not enough..
Chuck: What else is there?
Blair: The true reason I should stay right where I am and not get in the car. Three words. Eight letters. Say it... and I'm yours.
Blair: Thank you. That's all I needed to hear.
- The episode title is based off the movie Some Kind of Wonderful.
- Chuck calls his PI Mike, but in any episode after, his go to PI is named Andrew Tyler.
- The White Party took place on August 30, 2008 at 5:00 PM