Con-Heir is the 18th episode of the fifth season and 105th episode overall.
Spring is the season of rebirth. A time for change. A time to blossom.. but there are always late bloomers. And some buds are nipped before they can grow. New relationships flourish and take on new form. While old relationships can be reexamined. But some things never change. This is the Upper East Side in case you forgot.
Chuck invites Jack to town to thank him for saving his life, but finds the trip doesn’t go as planned. Blair and Dan attempt to consummate their new relationship, but unexpected roadblocks get in their way. Meanwhile, Ivy finds a quite unlikely ally in William van der Woodsen in her quest to be accepted on the Upper East Side, and Nate is hopeful that a new investor will save The Spectator.
The episode begins with Serena doing the usual Gossip Girl voiceover, narrating the opening of her newest blog post. Meanwhile, Blair arrives at Dan's loft dressed in lingerie ready to consummate their relationship, but is shocked to find Lily, Rufus, and William there having breakfast. Lily offers to let her join and she agrees to. At The Empire, Jack and Chuck arrive back after spending the night partying. Chuck says he's dedicating a new wing at the hospital in Jack's name as a thank you gift for Jack donating the blood that saved his life after the car accident. Back at the loft during breakfast, Lily is complaining about life in Brooklyn, and asks William if he's found a solution yet. He says that since the will is legally fine, there's nothing he can do. Rufus jumps in that he and Lily have a meeting with Bruce Caplan later and that it's better if they got their legal opinions from an expert. Lily says they can't let Ivy get between them and Dan suggests they leave quickly to get a jump start on their day. Elsewhere outside, Lola receives a call from Ivy asking if she saw what Lily and Serena said about her in The Spectator. Ivy recites the article, how they said her father's fatal overdose sparked her lifetime of criminal behavior, and says she isn't a criminal. Lola replies that she isn't sure if she is or isn't and that it might be best if she stopped calling her.
At The Spectator, Lola arrives with coffee for Nate. She runs into Serena, who asks if she would be willing to be interviewed on the story she's writing on Ivy. Lola says she doesn't want to get involved, but Serena argues that she already is since it was her identity that was stolen. Lola again says no, and Serena takes the hint. She then talks to Nate and says that while she wants to try and fit into her family, she doesn't know how. Nate asks if she ever called William back, and since he was the executor of CeCe's estate, he's close with the family and might have some ideas. Lola agrees that's a good idea and wishes Nate luck on his big investor meeting. Elsewhere outside, William is on the phone with Carol. He explains to her that he can't just overturn the will because she's blackmailing him and she replies that he can either pay her himself or get ready for his children to hate him. William reminds her that Lily will never forgive her, but Carol doesn't care. At the loft, Blair and Dan are finally alone. Blair says that every botched attempt at intercourse the past month has brought to them every potential problem so they're finally ready. As they begin to kiss, several car alarms begin to sound, ruining their chance once again. Back at The Spectator, Serena receives a package. Nate asks her to consider taking it easier on Lola, but Serena doesn't want to hear it. She opens her package, which contains the Gossip Girl laptop and a note from Georgina, telling her that the power of Gossip Girl is now in her hands and warning her that anonymity is key.
At their meeting, Bruce Caplan tells Rufus and Lily their only real option is proving CeCe wasn't of sound mind when she wrote the will, but everyone he talked to said her mind was sharp until the end. He finishes that the courts will only freeze the assets and grant a hearing if there was evidence of wrongdoing on Ivy's part. Lily says that she pretended to be her niece and that's wrong, but Bruce said that evidence would only work if CeCe had named Charlie Rhodes in the will, but she didn't. Lily is sure she did something illegal, they just need to find it. At the VDW's, Ivy is not having any luck finding any designers or decorators since no one on the Upper East Side will talk to her. William shows up and offers to assist her. She says she'd do anything to stop Serena and Lily from blackballing her, and William suggests she throw a party, and everyone will come if it's a benefit for the CeCe Rhodes' Cander Foundation. He offers to make sure everyone shows up and the party will succeed, so long as she pays him. At The Spectator, Nate is meeting with a new investor, James McKenzie. While touring the office, the investor meets Serena, who is investigating the GG laptop, and Nate says her blog is one of the paper's biggest assets. Mr. McKenzie is impressed, and tells Nate to expect an official offer by that night. Nate thanks him and he leaves. He notices Serena has Gossip Girl up and asks if she's back. Serena says maybe, since she saw a post about Ivy throwing a party in CeCe's name. Nate says it's weird he didn't get the blast yet but Serena says he'll probably get it soon. Nate goes off to check another story and Serena makes her first post as GG: about the party.
At The Empire, Lola calls the front desk and asks if she can leave William a message since he wasn't in his room. She then sees him pull up out front and hangs up. She sees him walk in with Ivy, and overhears her say that Lily is coming and the plan is working. William says he still wants her check, but Ivy says she won't write it until both Serena show up. Upstairs in his suite, Chuck informs Jack that he talked to Nate, and while there was research being done on the article about him, it came up that Jack spent time at an English boarding school. Chuck explains that spending more than three months in Europe from 1980 to 1996 prohibits anyone from donating blood in the United States. He asks if anyone asked about it, but Jack says they did and he lied so he could save Chuck's life. Chuck accepts that and says he's headed to the hospital to check on preparations for the night. At The Spectator, Lola goes to see Nate. She explains to him what she saw between Ivy and William, and Nate tells her that it's illegal for a beneficiary to reward an executor because it would call the whole inheritance into question. He tells her to talk to Serena, since what she saw was grounds to contest the will in court. She has to get to class and tells him to keep it to himself before leaving. At the loft, Lily is looking through her boxes to find jewelry of CeCe's that she could wear to the benefit to remind everyone who her true daughter is. Rufus finds a necklace, and Lily responds that it's perfect. He then says he bought them some privacy, and Lily becomes excited, thinking they're moving into a hotel and out of Brooklyn. However, Rufus replies that she has enough stress and bought the room for Dan. At the hotel, Blair and Dan are ready, with no interruptions. They then have sex. Afterwards, both are quick to leave the bed and Blair get ready to leave. They agree to see each other again at Ivy's party and she leaves. Once she's gone, both lean against the door, unhappy with the event that just transpired.
Meanwhile at the hospital, Chuck learns his medical records are all missing. The secretary can only find Jack's file, but she can't share them with him due to confidentiality. Chuck says he only wanted to learn specifics to mention them in his speech, but the secretary confusedly asks if he's sure Jack is the only one who gave him blood. She then again says she can't release Jack's files and Chuck asks her to let the doctor know he wants to speak with him before the ceremony. She goes off to deliver the message and while she's gone, Chuck sits at her desk and looks at Jack's files. He sees that Jack has Hepatitis C and is therefore, an unacceptable blood donor. Back at The Spectator, Nate has told Serena what Lola saw. Serena doesn't believe him since Lola didn't tell her herself. Nate says he won't write anything until what Lola said is confirmed, but Serena says he can't anyway since it's her article. He then makes the decision to take her off the article about it, citing that she's too close to the situation. Serena then gets a call from William, who asks if she's going to Ivy's party. She says no, but William reminds her that it's an event to honor her grandmother and she should be there. Serena agrees to go, and once they hang up, it's shown that William is with Lily. He says now they only need her to write the check and Lily happily says it's their proof she's engaging in illegal activity, and the court will have to hear their case. Meanwhile, Serena is typing a Gossip Girl blast about Ivy bribing an executor and sets the timer for it to post at 8:00 that night.
Blair goes to see Dorota at her apartment in Queens, and gives her a gift for her new baby, Leo. Dorota quickly realizes the champagne glasses inside the box are a regift from her wedding to Louis. Blair quickly finds some vodka and says they should break them in together. At the same time, Dan goes to see Nate at The Spectator. He asks if they can have a drink, then helps himself to some alcohol Nate has in his office. Nate asks if it has something to do with Blair, but Dan says they just need time for their relationship to find groove. Nate deducts that the sex was bad and Dan assumes that it's her that's bad at it. In Queens, Dorota asks if there's an anatomical reason Dan is so lonely but Blair says it was the sex itself, not Dan. At the office, Dan tells Nate it was terrible and Nate replies that it's probably just him overthinking. In Queens, Dorota asks what Dan said when Blair said it was only so-so. Blair says she didn't, but Dorota says that she needs to communicate with Dan to find answers. At the office, Nate also suggests Dan talk to Blair about it.
That evening, Lily arrives at the party and runs right into Ivy, who thanks her for coming. She says CeCe would want them to be close, but Lily says they were only close before under false pretenses. Ivy then asks a photographer to take a picture of them for CeCe. At the hospital, Chuck introduces a kid with leukemia named Michael to Jack. He explains that he decided a blood drive would be a better thank you than a simple ceremony. Chuck calls a nurse over, but Jack says he can't give the kid his blood. Chuck then dismisses Michael, and reveals he was a paid child actor who he set up to make Jack confess that he can't donate blood. He continues that he knows Jack has Hepatitis C and since he doesn't have it, it's clear Jack didn't donate the blood. Back at the party, William says the party was a success and he needs his check now. Ivy says she'll write him the check right after she talks to Lauren San Domingo, and runs off. Serena asks Lily how she;s holding up, and Lily admits that it's hard but she's taking it in stride. She explains her and William's plan to Serena, and that he was willing to be removed as executor to help them. Serena asks what she's waiting for and Lily says Ivy hasn't written the check yet, and warns her not to do anything to spook her from doing it. Serena checks the time, 7:56, and realizes she has to stop the blast. She goes to find her old computer but is stopped by someone who hold her up for a minute. Downstairs, Blair arrives and sees Dan in the lobby. She asks what he's doing there, and he says he's going to the party. Blair drunkenly says there's nothing to talk about, and Dan agrees. Upstairs, it's 7:58, and Serena finally gets away when she runs into Lola, who tries to tell her about Ivy. Before she can get away, the blast comes in, and everyone sees. Serena knows she ruined everything. Ivy confronts William and Lily for coming to humiliate her, and says she didn't bribe him. William says she tried to, but she says he offered and they have no real proof she did anything wrong. Serena begs Lola to come forward since her witnessing it makes it so she's proof. She hesitates, saying it seems like William was in on it. Serena says she sent the tip in, and that it's Lola's chance to save their family. She continues that since Lola doesn't know who her father is, the VDW's are the only family she has. In the elevator, Dan says Blair is wasted, and she says he is drunker than she is. She then comes out and says she wasn't honest with him, and that the sex was terrible. Dan agrees, saying it was boring, and then that Blair was good in his head. Blair argues that she is really good out of it to, and says she'll prove it. They then hook up in the elevator.
At The Empire, Jack admits that while he has Hepatitis C, it hasn't slowed him down. Chuck says he was just trying to cover for the real donor, Elizabeth. Jack confesses that she didn't want him to know, and Chuck replies that he wants to thank her. Jack says she's unreachable and it doesn't matter why he's alive, because he is. He then tells Chuck they'll do it again on his turf next time, and leaves. Back at the party, Serena, Lily, and William are about to leave the party. Ivy threatens to have security throw them out, but Serena says they're just waiting for the elevator and Lily promises she'll be back because this is her home. Ivy announces that she cares about CeCe unlike them and only came to debase her with more lies. Lola then chimes in that it wasn't a lie, and that she heard Ivy offer to pay William. Ivy says that she didn't and they're just trying to set her up, but Lola replies that she only know what she saw. Lily begins to call her lawyers to begin proceedings, and William says that until the courts decide if it was wrong, the assets will be frozen. Ivy demands to know why Lola is taking their side, and Lola says they're her family. The VDW's, William, and Lola then leave. Downstairs, Blair and Dan get into a cab and head for Williamsburg to drink more and hook up. In the lobby, William thanks Lola for coming forward. She apologizes for jumping to conclusions, and William says it's hard to know what to think when no one tells you the whole story. He tells her that Carol is only concealing things because she thinks it will protect her. He encourages her to talk to Carol and work it out, since it took a long time for him to rebuild a relationship with Serena and Eric after many years. Lola wonders if all her dad would want is to know her, and William says he's sure he does. He lets her have his cab and sends her off. Meanwhile, Serena goes to The Spectator to see Nate. He says Mr. McKenzie saw the Gossip Girl blast and backed out, saying since Nate couldn't deliver on that, he can't be trusted with other things. Serena apologizes and says she wanted to help her family. and Nate fires her. Serena grabs the GG laptop and leaves. At the loft, Lily worries that Ivy will drag out the case and suggests they find another apartment. Rufus says it took him awhile to get used to the UES, and helps Lily make tea. At the VDW's, Ivy is presented with the bill for her party. Since her assets are frozen, she asks if she can pay with her credit card and the man says no. In Williamsburg, Blair and Dan are still drunk and then hook up in an alley. At The Empire, Chuck calls his PI Andrew Tyler and tells him to track down Elizabeth. In a car, Jack is on the phone with a mystery person, saying Chuck figured out he didn't give him blood and says they should come back to handle it themselves. In his room, Nate is with Lola and apologizes to her for telling Serena what he saw. She says it's okay and that she's glad everything is on the table. They begin to kiss when Nate gets a phone call about a possible new investor: Diana Payne. At the Waldorf's, Serena is writing a new Gossip Girl post when she gets a message from Gossip Girl herself, saying that while she's doing a pretty good job, she's not the real deal and she wants her site back.
- 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
- Kaylee DeFer as Ivy Dickens
- Kelly Rutherford as Lily van der Woodsen
- Matthew Settle as Rufus Humphrey
- Desmond Harrington as Jack Bass
- Zuzanna Szadkowski as Dorota Kishlovsky
- Ella Rae Peck as Lola Rhodes
- John Bolton as Bruce Caplan
- Control Yourself (Bonus Track) by Dr. Dog
- Moon Comes Up by Boy in a Box
- Angel by Mr. Little Jeans
- Misery by Veronica Falls
- Some Place by The Wind
- Stars by In Waves
- This City by In Waves
Chuck: But I would wear something more suitable when I thank you officially for saving my life.
Jack: From that arsonist Russell Thorpe? That was a year ago. Took you long enough.
Chuck: No, no, no. I'm referring to the car accident. Your blood donation. After my body rejected the first transfusion and I needed a family member. I wouldn't be here without you. I'm eternally grateful.
Jack: Yeah, well, I considered letting you die and taking your billions... that's probably why you let me have all the hot ones last night.
William (on Rufus and Lily's meeting with Bruce Caplan): He won't tell you any different.
Rufus *quietly*: William, what are you even still doing here?
William: You hired someone to play our daughter.
Carol: Yes, which should give you some sense of what I'm willing to do to get my money.
Blair: Wait... do you feel that?
Blair *nodding towards the shelf*: It's like someone's watching us.
Dan: Um, it's just, Cedric.
Dorota: Don't tell me there anatomical reason he always so lonely-
Blair: Dorota! No! Everything down... there was appealing, but it wasn't the man, it was the... deed.
Nate: Hmm. Sounds like a classic case of the Dan Humphrey Overthink.
Dorota: It took honest communication to turn Vanya from boy to man in bedroom.
Blair: I'm gonna need another drink to forget I just heard that.
Jack *sees kid in wheelchair*: Since when do ribbon cuttings involve crippled kids?
Chuck: I wouldn't call him crippled to his face.
Jack: Sorry kid but let's face it. You're crippled.
Jack (to Chuck): We're all the family we need.
Ivy: I can't believe you're taking their side. They're just using you and when they're done they'll throw you out, just like they did me.
Lola: No they won't. They're my family.
- The episode title is based off the movie Con Air.
- Ivy's party was held on March 24, 2012 and cost $31,562.50.