It-Girl Interrupted is the 19th episode of the fifth season and 106th episode overall.
Every once in awhile, a life changing event will arrive with fan fare and excitement. In my experience, most turning points in our lives don't announce themselves. If anything, they tend to creep up quietly when we're least expecting them.
Serena decides she is ready to relinquish the spotlight and sets out to make a reluctant Lola the next "It Girl" of the Upper East Side, starting with modeling at a Kiki de Montparnasse lingerie show. Meanwhile, Chuck reaches out to Blair for advice about his past, and Diana Payne's return to The Spectator starts a power struggle with Nate.
The episode begins with Dorota delivering Blair's divorce papers to her. Blair becomes excited, as she can now date Dan in the public eye without having to worry about the Grimaldi's or dowry. Dorota wonders how Georgina worked the deal out, but Blair says it's better to be blissful in ignorance in this case. In her room, Serena is deleting all the Gossip Girl tips about her and her lack of a love life. While doing so, a message from the real Gossip Girl pops up, saying she's had it for a week and she has until the end of the day to return it. Serena replies that she wants to return it but has to do one thing first. At The Empire, Chuck tells Nate how Jack isn't returning his calls and Andrew can't track down Elizabeth. Nate asks if Chuck wants a relationship with her, and Chuck isn't sure but says he has time to think since she's MIA. Nate says he's headed to the office since Diana will be showing up that day, but that she's only an investor and he's still editor in chief. Chuck asks how Lola feels about Nate's ex being around, but Nate admits he hasn't exactly told her about his romantic history with Diana. Nate promises her return means nothing to him, but Chuck says it might mean something to Diana. Nate replies that once he gets the lay of the land with Diana, he can come clean to Lola. At the Waldorf's, Serena congratulates Blair on finally getting her divorce papers. Blair then gets a Gossip Girl blast on her divorce, and she wonders how she already knew. Serena suggests someone might be staked in front of the building, and then mentions that how she hasn't been mentioned once since Gossip Girl returned. Blair replies that since Serena is modeling a line of lingerie named after her that night, Gossip Girl won't be able to resist talking about her. When she realizes Serena is serious about wanting to stay off her radar forever, she suggests she find a new It-Girl that everyone wants to talk about. Blair reasons that the new girl needs to have a defining moment, like Serena in her wet white dress in night grade.
Elsewhere outside, Lola is walking around with an old friend from Florida, Aidan, and telling him about her new family. She confesses she would like to get to know Serena a little more, and Aidan says she can't get to know her unless they spend time together. While they walk, they run into Nate. Lola introduces them and asks if he wants to hang with them. Nate rejects the invite, saying he needs to go meet with Diana. Lola asks what he knows about her, and Nate brushes her off and walks away. Lola remarks to Aidan that that was weird and decides to look on Gossip Girl to see if there's anything about her. She finds an article on Diana and Nate from when they were a couple. At the Waldorf's, Dan proposes a day full of activities for him and Blair. However, Blair says the royal seal is missing from her divorce papers and she doesn't want to be caught on a technicality. Dan says if it's that small, it can probably be fixed that day, but Blair says the Grimaldi lawyers work very short hours. Blair says she'll call him later and walks away. Dan notices the papers on the table, and is able to convince Dorota to leave the papers for him to look at. Because she's worried, Dorota leaves him with the papers. Dan opens the packet, and finds that not only did Louis sign, but the royal seal is also there. He also notices that Blair hasn't signed yet. At The Spectator, Nate arrives to find Diana setting up in his office. He demands to know what she's doing there, and she says she gets an office and wants his. Back at the Waldorf's, Serena is going through tabloids and circling potential new It-Girls when Lola arrives. She says she just found out that Diana is the new investor and also Nate's ex, and that he lied to her. Serena then realizes she found her solution and tells Lola she knows what to do, and the two leave. At The Spectator, Nate says her being an investor entitles her to nothing and that his name is already on the masthead. Diana says advertisers won't want to do business with Nate now that she's back, and she knows advertisements are down, and she's hosting a Down to Your Skivvies party to bring it back up. Nate replies that she can't host a party for the paper without him, and Diana grudgingly agrees. She assumes he'll have no plus one but he tells her he'll be bringing Lola. At the loft, Lily asks Rufus if he wants to go have lunch and then go to Barney's. Rufus says he just came back from the city, where he saw Ivy, and asked if she would move out of the apartment in return for having the assets unfrozen. Lily is horrified, but Rufus continues that Ivy agreed to leave as soon as Lily calls her lawyer. Lily says that while it was a nice gesture, she can't live with letting Ivy have CeCe's money. Rufus reminds her that she has plenty of money, and Lily agrees to call her lawyer.
At The Empire, Chuck is meeting with Andrew Tyler, who tells him Elizabeth has been living in Vienna for the past six months, but that he hasn't made contact. He asks how Chuck wants him proceed, and Chuck confesses that he isn't sure. Andrew says at this point Chuck might need a friend more than a PI. He suggests he talk to anyone who got to know Elizabeth the last time to help him decide, but Chuck replies that the only one who did is the only one not in his life anymore: Blair. Andrew asked why he paid her dowry then, and Chuck says that she doesn't know and he doesn't ever want her to find out. Meanwhile, Serena and Lola are at the shop where the lingerie show will be held. Lola asks if she's overreacting about Nate, and Serena says that while Nate's a great guy, Diana is very aggressive and she's probably back for Nate. She also says that even if Diana wasn't back, Lola not wanting to be a part of his world is an issue, since sharing interests is part of being in a relationship. Lola argues that she has no interest in the UES, but Serena replies that if she doesn't meet him halfway, he'll look for someone like Diana, who will. Serena picks up a piece of lingerie and convinces Lola to try it on. She waits until Lola has it on, then pulls the fire alarm. She grabs all of Lola's clothes and yells that they need to leave. They head outside, Lola still in the negligee. At The Spectator, Dan explains to Nate about Blair having the divorce papers but not signing them. Nate says he's Humphreying out. Diana comes in with recent numbers, announces they're dismal, and leaves. Nate admits that Chuck was going to invest, but he wasn't liquid enough. Dan asks how that could be, and Nate reveals he paid Blair's dowry. Dan realizes that's why she didn't sign the papers. Nate says he was just trying to do a nice thing, but Dan reminds him that it is Chuck before leaving.
At the Waldorf's, Blair is about to leave when she's stopped by Dorota, who asks why she lied to Dan about signing the papers. Blair says she is going to sign them eventually, but that she isn't ready to let go yet. The elevator comes up and once the door opens, she sees Chuck inside. Upstairs, Lola sees a photo of herself in the negligee on Gossip Girl. Serena says that the photo combined with her being the real Charlie Rhodes means everyone will be talking about her. Serena then gets an email from Tracy from the shop asking for Lola to model at the show. Lola says no, until Serena says it will impress Nate and show Diana, who is one of the party sponsors. Serena then gets an email from Diana, asking her to post that she'll be attending the show with Nate as her date. Lola is getting ready to leave, and while she does so, Serena quickly types and sends a blast. She tells Lola to check Gossip Girl again, and she sees the blast for herself. Downstairs, Chuck is confessing his feelings about everything involving Elizabeth to Blair. She asks what he wants from her, and Chuck admits he just wants someone to talk to who will understand. She says she's not the one to ask, but Chuck says he's truly coming to her as a friend who needs help. Blair isn't convinced and tells Chuck she thinks he's using his mother as an angle to work his way back into her life. She walks off and he goes to leave when be bumps into Serena. She asks what he's doing there, and he sadly says he thought he was coming to ask a friend for advice, but was wrong. He tells her about the blood transfusion, and Serena says that he should do it because reconnecting with family is worth the risk. At The Spectator, Nate is trying to convince Lola that Gossip Girl was wrong and he isn't going to the party with Diana. Lola says he already lied to her about Diana and is probably doing it again. He apologizes, and Lola asks why he keeps looking at the door. Nate explains that Diana is determined to kick him out and the last thing he needs is a fight with her where Diana can see. Lola tells him they can talk that night, but he says no, since he has to go to the party. He promises her that it's a work event and not a personal one. Elsewhere outside, Dan gets a Gossip Girl blast about Chuck leaving the Waldorf's. He calls Blair, and accidentally reveals that Chuck paid her dowry. Blair insists she had no idea Chuck paid it and hangs up, deciding to go find him. At the loft, Rufus gets a call from Ivy's lawyer. He says that Ivy received a call from the bank saying there was a cashier's check waiting for her, and that she packed up and left the apartment but when she got to the bank, they had no idea what she was talking about. At The Spectator, Diana announces she overheard Nate's fight with Lola. She suggests they go together, but Nate says that sends the wrong message. Diana insists that it looks good that the paper is doing well and it will be good for business. At the Waldorf's, Lola fills Serena in on the new Nate developments. Serena says she has two options: to stay home and worry or to come and model. Lola says she'll be at the show with a date.
At the show, Lola arrives with Aidan. She sees Serena, who assures her that once Diana sees her model, she'll realizes she's a force to be reckoned with and her and Nate will be the hottest couple. She pulls her to start getting ready, but Lola says she wants to introduce herself to Diana first. She does, and also tells her that she was invited to model. Nate says he didn't know that, and Lola says he wouldn't have any reason to. Aidan attempts to hit on Diana, but she says she and Nate have more people to say hello to. She warns Lola to not lose two men to her in one night and walks off with Nate. At the loft, Rufus tells Lily he knows what she did. She admits she never called her lawyer and now that she's out, she needs to make sure she can't get back in. Lily insists she did nothing wrong, and that after everything Ivy has done, she deserves everything that's happening to her. Rufus says she lied to him to, and that he's not okay with it. She asks if they can just pack and go home, but he says right now the loft feels more like home. Back at the party, Diana tells Nate that everyone is excited she's back. Nate says he thinks Diana came back for him, and that she was unable to convince herself that Nate was just a fling and can't move on. Wanting to prove him wrong, Diana finds Aidan and kisses him. She pulls him aside, and Lola comes up asking where he's going. Nate replies that they're both going right where they want him to. Blair then arrives and confronts Chuck. He admits to paying the dowry, but denies doing it to "buy" her. He promises he only wanted her to be free and whatever she wants to do with that freedom is her choice, then walks away. Dan then shows up and apologizes for telling her. In a dressing room, Diana begins to strip Aidan, preparing to hook up. Meanwhile, Nate and Lola are in the next room, recording her. Serena then opens the door and becomes angry at the two, especially Lola for using her. After the girls walk off, Diana then walks in. She demands to know what he's doing, and Nate says Aidan is only sixteen and she can't run The Spectator from jail. Diana tells him he can release the video, because recording and distributing child pornography is also a crime. Nate realizes she's right. At the same time, Blair and Dan are talking. She admits she isn't used to seeing Chuck be selfless, and Dan says people can surprise them. Blair admits that her not signing had nothing to do with Chuck, but that she always wanted to be a princess but never really got to be one. Backstage, Lola apologizes to Serena and says she only agreed to come to the party to make it look like she was fighting with Nate. She says that she knows Serena wants the It-Girl thing for her but it has no appeal to her, and Nate doesn't care either. Serena says all Lola did was let her down, and then tells Tracy that Lola won't be modeling. Tracy then informs Serena that after the photo earlier got so much attention, they thought they'd get more buzz if it was named The Lola and not The Serena, so they changed the name. She tells Serena she can't model The Lola, and says she can model something else.The next day, Serena gets another message from the real Gossip Girl telling her to give her her site back. Lola then arrives and apologizes again for the night before. Serena accepts her apology and apologizes for pushing her. Lola says she got a call from an agent and wants to set up a meeting. Serena asks what Nate thinks, and Lola replies that he's happy for her. She continues that if she's an It-Girl, she wants to add an every girl vibe that more people can relate to. Serena warns her that these kind of things are fleeting, and Lola accepts that. Serena offers to hang out with her late, and she leaves. She goes back to reading Gossip Girl emails and sees that everyone is now asking for information about Lola. At The Spectator, Diana asks to talk to Nate. She tells him that she didn't realizes how upset he was at her, and she wants to find a way for them to work together. Nate says he doesn't know if they can, and she apologizes for not being honest from the very beginning, including working with William. She also admits she took the fall for revealing the Gossip Girl sources (All the Pretty Sources) because she wanted to punish herself. Finally, she finishes by saying that The Spectator is his and that she has other business to be her main focus, and she found another office downstairs. She also admits to still having feelings for him, but that she won't let her feelings dictate their work or his relationship. Meanwhile, Chuck meets with Andrew, who tells him he made contact with Elizabeth and she said she was at a monastery in Tibet when Chuck had his accident. Chuck replies that she's lying, but Andrew says he looked into it and her story checked out. He tells Andrew to keep looking because he wants to know who donated the blood. Elsewhere outside, Dan brings Blair to the Met steps in a evening gown and a tiara. She asks what's going on, and Dan says he wanted her to feel like a princess one last time. Several young girls then run up Blair, out of their minds excited to meet her. They ask Dan to take a picture, which he does. Elsewhere outside, Lola gets a blast claiming that her photo in lingerie was staged and the only real It-Girl is Serena. She tries to call Nate, but is told he's in with Diana. She then sees paparazzi, and decides to let them take her picture. At the VDW's, Vanya brings Lily's stuff up, and asks to get Rufus' stuff. She sadly tells him it's only her stuff for now, and back at the loft, Rufus isn't packing to come home. At The Empire, Chuck gets a text from Blair thanking him for setting her free. At the Waldorf's, Serena finishes her post saying that she's there to stay as Gossip Girl.
Chuck (to Nate): You sound like you got it all figured out. Just don't be surprised if you end up with an angry ex girlfriend and a tattoo of a kangaroo.
Blair (to Serena): It is your destiny to be gossip worthy.
Diana (to Nate): You never did understand that sex sells.
Lily (to Rufus): We do not negotiate with terrorists! Especially ones from Florida!
Chuck (on the Elizabeth situation): The only person who was there the whole way through is the only person not in my life anymore. Blair Waldorf.
Diana (to Nate): The editor in chief is chitchatting with his "bro" instead of working. And you wonder why the paper isn't doing well.
Blair (to Dorota): I feel like once I sign those papers I'm closing the door on something I'm not quite ready to let go of.
Aidan: They do not have parties like this in Florida.
Lola: They barely have dental hygiene in Florida.
Lily: Can we please just.. stop fighting, and just pack and go home?
Rufus: I don't know, Lil. Right now, this loft feels a lot more like home than our apartment.
Blair: I knew it. You thought you could buy me back. Just like you thought you could sell me for your hotel.
Chuck: You've got it all wrong-
Blair: Thats why you showed up today with that rouse about friendship. You bought my divorce and you came to collect your prize.
Chuck: Then why didn't I collect? I swear, I did not want you to know about the dowry. The only people who knew were Nate and Andrew Tyler. I only wanted you to be free. Whoever you choose to love with that freedom is up to you.
Blair: My whole life I wanted to be a princess. When I met Louis, it was this whole whirlwind of royalty and tiaras and it seemed like my dream was coming true. I mean, I may have married a prince but I never really got to be a princess.