Dr. Estrangeloved is the 19th episode of the third season and the 62nd overall.
On the Upper East Side, new days don't always bring new beginnings. But they almost always bring new surprises.
When Lily's ex-husband, Dr. William van der Woodsen shows up unexpectedly in Manhattan, Serena finally gets the reunion she has so desperately wanted with her father, but the circumstances turn out to be far from ideal when Will reveals a secret of Lily's failing health. When Serena and Nate continue to have relationship issues, a scheming Jenny is more than happy to be a shoulder for Nate to lean on. Meanwhile, Dan finds out that he didn't get accepted into the Tisch writing program and Vanessa admits she may have been somewhat responsible by acquiring the spot that Dan wanted in the first place
At The Empire, Nate and Jenny have waffles together after having a sleepover. Nate notices Jenny is wearing one of his shirts and he tells her that it's Serena's favorite to sleep in too. She asks if he's heard from her since the wedding but he answers that she hasn't and he doesn't want to be the first to talk. While they eat, Nate gets a text from Serena that she's on her way home and he decides to go meet her at the VDW's. He ruffles Jenny's hair, much to her dismay, and goes off to take a shower. Meanwhile, Lily and Serena are on their way back into the city. Serena asks Lily if she's ready to tell Rufus the real reason she was lying about her whereabouts and she answers that she's not, especially since Dr. van der Woodsen is involved. At the Waldorf's, Dorota attempts to sneak up on Blair, who asks if the caterers are done setting up downstairs. Dorota says they are, then says that the party that's planned isn't a good idea. Blair reminds her that it's to show that she's available and over Chuck for good. She then instructs Dorota to throw out a box labeled "Old Life", inside which Dorota finds a photo of Blair and Chuck, along with any significant belongings that related to their relationship.
At the VDW's, Rufus hears the elevator ding and is surprised to find William van der Woodsen entering the apartment. He asks where Lily is, and Rufus tells him to leave. However, he doesn't and tells Rufus that clearly Lily hasn't told him the whole truth because they have lots to talk about. Back at The Empire, Chuck arrives home, drunk, with two prostitutes that he shoos into his room. He asks where Nate is, and that he's noticed Jenny trying to flirt with Nate. She tells him that Serena is back in town, to which he replies she might actually have a chance now. He tells her that if she can break the two of them up, maybe by making Serena think he cheated on her, he'll be free to come to her. Jenny asks why he's telling her that, and he says that he wants Nate to be the way he was before he started dating Serena. Before leaving, Jenny grabs the shirt she slept in and stuffs it in her purse. Back at the VDW's, Lily an Serena arrive home and find William waiting with Rufus. Right after they arrive, Lily tells Rufus that CeCe was never sick: she was, and that's why she was with William during the summer. He was treating her cancer. Serena says that that's why he didn't see her when she came looking, and William agrees. Lily also says she just had her six month check up and everything is looking good so far. Rufus apologizes for her having to go through being sick alone, and she asks to be treated normally and for them to not tell anyone else. She then goes upstairs to freshen up and Rufus asks William to leave. He agrees to go, and asks Serena if she would like to meet up and talk. She accepts his invitation and plans to go to his hotel after she changes. Rufus asks if she's okay, and she replies that after everything he did for Lily she at least owes him a conversation.
At the loft, Dan reads Vanessa his letter of denial from Tisch. Guilty, she admits to him that she got in and took his spot. Shocked, Dan congratulates her and tells her he's glad for her. He leaves to go to a study group and asks her to go to a party in Bushwick with him later that night. Glad he took the news so well, Vanessa agrees to go with him. Back at the VDW's, Rufus asks Lily why she didn't tell him about her being sick. She says that she was too scared, both for him and for herself, and William told her not to say anything so her body wouldn't act sick. Suspicious, Rufus clarifies that William told her not to say anything. She replies that everything he has said to do has worked, and Rufus doesn't object. Back at the Waldorf's, Blair is shocked and disappointed that no one showed up to her party, and blames Dorota for not sending the invitations out. She asks a cater waiter if he would date her, since she invited a dozen eligible bachelors that didn't come. Dorota shoos him away and begins to tell Blair about a similar situation with her first husband. Before she can really say anything, Blair realizes Chuck was probably the one who sabotaged the party. At the VDW's, Jenny runs into Serena in the lobby of the building. She pulls the shirt out slightly to make it visible, and Serena excitedly tells her that she's on her way out to see her father. She excuses herself, but not before seeing Nate's shirt. Jenny explains that she just fell asleep while they were hanging out but didn't do anything. She hands her the shirt to return to Nate but Serena tells her to keep it, since she'll probably see him before she does.
Meanwhile outside NYU, Dan runs into Willa and she expresses her condolences for his rejection from Tisch. He admits to her that it really sucks because her submission was based on a piece he wrote for The New Yorker, and she replies that submissions have to be original work. She also mentions that her dad was on the admissions committee and he was their second choice candidate. When Dan is surprised at how close it was, she offers to call her dad and tell him about Vanessa's submissions. He tells her not to, not wanting to ruin her opportunity and leaves. When he's gone, Willa calls her dad anyway. In the lobby of the VDW's, Serena is surprised when Nate arrives to see her. She tells him that she's headed out to see her father, and asks him to wait. He flatly tells her that he's been waiting, and they argue briefly over who his being dishonest. Unbeknownst to both of them, Jenny overhears the whole argument. Afterwards, she calls Chuck to get advice on the next step; and he tells her to come over at six dressed up. When they hang up, Blair arrives at The Empire to confront Chuck on ruining her party. He reasons that no one came because everyone knows no one can ever measure up to their relationship, and Blair threatens to be with someone outside the UES just to show him up before leaving. Meanwhile, Dan gets a call from Willa, who tells him that she called her dad and is having Vanessa thrown out to get him in.
At William's hotel, he sits with Serena in the lobby telling her about some of his adventures. She listens intently, and then shares what happened in her life since he left. He suggests they go get banana splits, but then apologizes for trying to know her because he really doesn't. She tells him that nothing explains his absence the last fourteen years, and he replies that it didn't happen the way she thinks it did. At NYU, Dan mentions how Tisch wanted an original piece for the application to Vanessa. She gives him a copy of her submission and tells him that while it wasn't based on anything he ever wrote, it was based on him and their relationship. She then suggests they skip the party and just hang out alone instead. Back at the hotel, William explains that he wanted them to come with him to Tibet for a job, and he tried to commute while they worked out the details; but Lily grew tired of the arrangement and asked for a divorce. He admits he couldn't blame her for wanting consistency, and he never meant to abandon them forever. She begins to understand that he forgot how to be a father, and then William spots Rufus at the front desk. He excuses himself to see what he wants, and Rufus explains that he came to make sure he leaves because he doesn't want him to take care of Lily anymore. Serena then comes up, and offers to go home with Rufus. She tells William she just needs some time to think and leaves. Meanwhile, Dan is unable to reach Willa and becoming desperate. While he's leaving her another message, Blair enters the cafe and corners him. She explains that Chuck is preventing her from dating someone new and she needs a night away from Manhattan. Dan realizes that he can bring her to the party he was going to with Vanessa so he can talk to Willa, and agrees to take her.
At the VDW's, Rufus encourages Serena to not let his issues with William prevent her from pursuing a relationship with him. As they enter the apartment, Lily is hanging up the phone. She sadly tells them that William got the test results and they're not what they hoped. At The Empire, Chuck hangs up with Blair's dorm RA, who he paid to find out where she is and what she's doing. Nate arrives home and Chuck asks him what's wrong while offering a drink. He then suggests they get out of the city together, and Nate agrees to go along. Chuck says he wants to go to Brooklyn, and he invited Jenny to come since she's a local. At the party, Blair arrives with Dan and Vanessa. She excitedly tells them that by the end of the night, Gossip Girl will have a picture of her kissing a new guy and Chuck's threats will be empty. She walks off, and Vanessa asks Dan if she's sure he wants to be there. He assures her that he does and he doesn't want the Tisch thing to come between them. Vanessa decides to follow Blair, and Jenny arrives with Chuck and Nate. She goes to get drinks and Nate voices his disdain for Chuck inviting her to come with them because she's just a kid. Chuck reminds him that she's a junior and doesn't really look like a kid. At the bar, Blair meets a guy named Cameron who attends Columbia. They begin to talk, and then she notices Chuck with another girl. She pretends to be dizzy, falling into Cameron's arms, but quickly picks herself up. Meanwhile, Dan finds Willa, who tells him that she didn't get any of his messages. He explains that Vanessa wrote an original piece so she needs to call her dad and undo what she did. She refuses, saying that Dan deserves to be there and then tries to kiss him. He pulls away, then he sees Jenny watching them. He tells Willa one last time to call her father and follows Jenny, asking if Rufus knows she's there. She answers no, then asks if Vanessa knows the girl that just tried to kiss him. While they talk, they both see Vanessa being told something by Willa.
At the VDW's, William explains that a relapse isn't uncommon and the next step is to do some more treatments. Rufus refuses, saying they should get a second opinion before anything else. William goes along with it, but says that even if she does go to another doctor, he's staying in New York. Serena jumps in and says they should stay with William, because he's already cured her once and is family. Lily agrees with Serena, and Rufus grudgingly agrees if it's what Lily wants. After the conversation, Serena calls Nate wanting to talk. But before she can say anything important, Jenny loudly tells Nate that Chuck wants them to do shots. Serena overhears and demands to know why he's with Jenny. He replies that they're at a party and assures her that it's no big deal. Annoyed, Serena hangs up on him. Back at the party, Chuck sees Blair flirting with Cameron and stares jealously. Jenny comes up and announces that his plan sucks since Nate's talking to Serena. Nate then comes up and says he's ready to go. Chuck tells the two of them to go ahead and leave because he wants to stick around. Nate asks Jenny if she's up for going home to hang out, and she says she is. Meanwhile, Blair is having fun talking to Cameron, who has figured out Blair is wanting to make someone jealous. He offers to help, and she accepts. Elsewhere, Vanessa tells Dan that she knows what he told Willa. He assures her that she has nothing to worry about since she wrote an original piece, but she asks why he didn't tell her he wasn't okay with her at Tisch. She sarcastically offers to retract her application, and he replies that she shouldn't but she couldn't have expected a great reaction from him.
Back at the VDW's, William is about to leave when Serena stops him to say she doesn't know yet what she wants from him. He says that he was planning to give her a big speech on regret, but now he thinks there's a purpose in Lily reaching out and asking for his help. He also tells her that he's follows her from afar, including seeing her steal the horse from the polo match (in Reversals of Fortune). Finally, he thanks her for giving him a second chance and she says that everyone deserves one. They hug, and he leaves. Back at the party, Chuck remarks to Blair that he hasn't seen her on Gossip Girl yet. She explains that making him jealous with a stranger isn't a good way to move on and one day she won't feel the need to play games with him anymore because she really has gotten over everything. At The Empire, Nate vents to Jenny, who assures him that he's really great and deserves way better than Serena. After they talk for a little bit, she leans over to try and kiss him. However, Serena enters the suite at that moment, in time to see Nate tell Jenny no. He asks Serena what she's doing there, and she explains that she came to apologize for not hearing him out earlier but regrets it now. Serena asks if everything Jenny said was true, and Nate says that he really does hate that she doesn't tell him everything, like the time she left with Carter. She apologizes for not telling him about looking for her father, but he knows she didn't leave with Carter because she left a message with Jenny explaining everything. Nate says he never got the message, and Jenny quickly says that Serena is lying to try and manipulate him. Nate then orders Jenny to get out, which she does, but not before saying sarcastically that they deserve each other. At the Waldorf's, Blair finds her box downstairs. Dorota says she forgot to get rid of it, and apologizes. Blair asks her not to, and admits she knows that Chuck will always be a part of her. Dorota recites an old Polish saying to her, and Blair asks to feed the ducks in the park the next day. Back at The Empire, Serena tells Nate that she does trust him and she knows she's guilty for taking advantage of him. She promises to not do it again, and then she tells him that Lily is sick. At the Waldorf's, Blair goes through her box and reminisces on her past with Chuck. At the VDW's, Lily thanks Rufus for sticking by her side and tolerating William. Elsewhere, Vanessa listens to an apology message from Dan but doesn't call him back. Finally, William talks on the phone to someone, telling them that the plan isn't working and he needs another prescription. He pauses, then tells them that they can't back out now; especially since the police wouldn't be happy to know what they have been doing.
- 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
- Matthew Settle as Rufus Humphrey
- William Baldwin as William van der Woodsen
- Zuzanna Szadkowski as Dorota Kishlovsky
- Megan Guinan as Willa Weinstein
- Ben Yannette as Cameron
- Percussion Gun by White Rabbits
- Ha Ha by Monsters Are Waiting
- Look Alive by Wait.Think.Fast
- Slang Tang by Discovery
- No One Just Is by Holly Miranda
- Dim the Lights by The Phenomenal Handclap Band (feat. Morgan Phalen)
- Drop Alcohol by Two Hours Traffic
- Quiet Assurance by Telegraph Canyon
- Two Weeks by Grizzly Bear
Jenny: Oh, God, waffles.
Nate: You don't like waffles?
Jenny: It's not a matter of like, it's-it's I'm a Humphrey so syrup is a food group.
Nate: Yeah, how are you not like five hundred pounds?
Jenny: You look like hell.
Chuck: Small price to pay to feel like heaven.
Blair: Dorota, I need answers that don't end in "and then I came to America!"
Blair: You twisted, manipulative, psychopath! How could you?
Chuck: You're going to have to be a tad more specific, it's been a busy few days.
William: Serena, I just don't want you to think I woke up one day and decided I was going to leave you and never come back. After awhile I just didn't know how.
Willa (on Jenny): Who's that slut?
Blair: I suddenly realized that the way to get over you isn't hooking up with some random guy or pretending like we didn't happen. You and I loved each other. Then you broke my heart. I've been doing everything possible not to face that fact. I'm going to kiss somebody someday. And when I do? It will be for me. Goodbye, Chuck. I'm going home.
- The episode title is based off the movie title Dr. Strangelove.
- The photo Dorota finds in Blair's box is a part of a promo cast photoshoot for season three of Gossip Girl.
- The episode features a flashback to season one's Victor Victrola.