Portrait of a Lady Alexander is the fourth episode of the sixth season and 115th episode overall.
Extra, extra, read all about it! The latest Upper East Sider to take upper stage in the social spotlight, but you know what they say.. if you can't take the heat, then move to Hell's Kitchen.
Chuck’s continued investigation into his father’s dealings leads him to find the one person who can help reveal the truth about Bart. Serena and Steven decide to reveal their romantic histories but are still surprised by an unlikely run in. With The Spectator in jeopardy, Nate must make a difficult decision to keep it in business. Meanwhile, Georgina pushes Dan to choose a worthy person to date to boost his image, but he finds himself drawn in a different direction. Elsewhere, Ivy tries to persuade Rufus to go through a group of boxes of things from the van der Woodsen's.
The episode begins with Nate reading Dan's serial about him to Sage. He complains that if Dan made stuff up, he would eventually get over it but that he's mad that Dan told the truth. He confesses that The Spectator is indeed in serious financial trouble because of his own actions, and that he hopes his meeting later will relieve some of the problems. Sage offers to come help and skip brunch with Steven and Serena, but Nate tells her to go and to be nicer to Serena, since she's the one who convinced Steven to let them keep dating. Elsewhere outside, Georgina and Dan are walking around, and Georgina says she's pleased of the positive attention the Nate chapter is receiving. Georgina then tells Dan that her plan to keep him relevant is to set him up with girls who have a good reputation and at least a little celebrity surrounding them. Dan asks how they're going to make that happen, and she says she already has the interviews set up. Meanwhile at Steven's, Sage arrives for brunch while he is venting about how according to Dan's article, Nate isn't someone good for Sage. Serena vouches that Nate is a good kind friend. Sage asks if he can come to the horse show to get to know Steven, and he reluctantly agrees. She thanks both Steven and Serena, then leaves for school. After she's gone, Steven shows the Nate article to Serena and asks when she planned to tell him she's slept with Nate.
At the loft, Ivy arrives to find it filled with boxes, and tells Rufus it's time to unpack them. Rufus says he's been so busy planning the opening to have done it yet, but Ivy replies that he's using that as an excuse to avoid going through his old life. She offers to unpack the boxes while he's at the gallery, and he takes her up on it. He leaves and she begins to unpack. The first box contains his Welcome Back Cotter mugs, his infamous waffle iron, and a shoebox. Inside the shoebox she finds a letter from Lily dated May 17, 2008, which cites a passionate night they spent together. Back at Steven's, he demands to know when Serena planned to tell him she dated Nate. She admits that she should have said something, but Sage knows and doesn't care so it's really no big deal. He suggests they reveal everyone they've been with to each other, beyond second base. Serena hesitantly agrees to after she runs an errand. Steven replies that they can when she comes back and walks away. She texts Dan saying they need to talk and asks where he is. At The Empire, Blair and Chuck are having no luck finding Lady Alexander. Meanwhile, Blair is avoiding calls from Eleanor about the fashion show failure. Chuck says he's starting to think Dave gave them false intel since they've having such a hard time finding anything. Blair replies that she has an idea that may be crazy, then explains that Eleanor has a friend named Lady Vaughn who changed her name to Lady to sound more important. She suggests that Lady Alexander did the same and conducts a search. A painting titled Lady Alexander by Brian Batt comes up, and Blair realizes she knows of the artist because he has a studio in New York. At the VDW's, Lily tells Bart that Eric texted her saying she was on Gossip Girl, and the subject was the night before their wedding when she slept with Rufus. Bart says that Chuck is more than likely the source, but Lily doesn't believe him at first, then realizes it might be why he hasn't been returning her calls. Bart promises to take care of it.
Meanwhile, Chuck and Blair pay Brian Batt a visit. They ask if he could do a portrait of Blair in the same pose as Lady Alexander. Confused, Brian opens his book of previous pieces and shows them a portrait of a horse while saying he hopes they aren't talking about the same Lady Alexander. Outside the studio, Blair searches to find the owner of Lady Alexander. She finds out she was sold four years ago by Bart and that she was sold for just under a million dollars. She also discovers that he bought a dozen thoroughbreds in a single month. Chuck takes her phone and sees that they were all bought from the same man in Dubai named Sheikh Hassan. Blair suggests that maybe Bart was just really into horses, and Chuck answers that he wouldn't pay off Amira if it were that simple. He announces he needs to find Sheikh when Blair remembers there is a huge horse show going outside the city that attracts an elite international crowd and maybe the Sheikh is there or has people there for him. Elsewhere at a restaurant, Dan is meeting with women set up by Georgina when Serena arrives. She agrees to let Serena talk to Dan for a moment, so long as she leaves her purse behind. Serena obliges and heads to his table. At The Spectator, Nate is on the phone begging an investor to give him a chance. Bart comes in and tells Nate that he knows the paper is in trouble, and that he also knows that he is smarter than the article made him sound. He asks for a meeting with Nate. Back at the restaurant, Serena asks Dan if there's a chapter about her. He answers that of course he did, but is interrupted when she asks if he included anything from when they last slept together. Dan answers that he didn't but only because it was the most humiliating thing he's ever been apart of. They argue for a moment until Serena gets up to leave. He stops her; but only to tell her to tell Georgina he's going to the bathroom. Serena takes her bag back from Georgina and tells her Dan asked for the next girl to meet him in the bathroom. On her way out, she calls Steven and says she finished her errand.
At The Spectator, Nate reiterates Bart's plan back to him: he writes good press on Lily in exchange for Bart backing the paper financially. He refuses, saying he isn't looking for any new investors. Bart accepts that, then reminds him how The Captain was always so inventive with numbers and maybe Nate inherited that. After he's left, Nate calls someone and tells them he has a business proposition. At The Empire, Chuck receives a call from Lily that he ignores. As he does so, she walks in and announces that at least now she knows his phone isn't broken. She asks why he's avoiding her, then asks if he spread the rumor on Gossip Girl. He denies it, and she tells him to end the fighting between him and Bart. He's in the middle of explaining how his relationship with Bart was always business when Blair runs in and says she got tickets for the show. Lily asks if it's the one at Stone Orchard Stables, and Blair reluctantly says it is. Lily suggests it's a perfect way to get Bart and Chuck on a friendlier track and decides to call him to ask if he can come. Chuck asks her not to and says it should be a surprise. At the loft, Nate drops by to propose a business offer to Ivy. He says he knows she put out the story about Rufus and the lawsuit so he figured she was also behind the Lily rumors. She reasons that Lily engages in despicable behavior constantly but never pays the price for the damage she causes and it isn't fair that Rufus is always the one made to look bad. Nate agrees and tells Ivy that Lily's friends don't read Gossip Girl so for maximum damage, she should put the information on The Spectator. Back at The Empire, Lily demands to know why they need to keep the horse show a secret from Bart. Chuck lies that the stable is for sale and it would be a new venture for himself that would ensure no competition with Bart, and he doesn't want to jinx it. Lily is delighted and agrees to keep things quiet, so long as she gets to come with them.
At Steven's, Serena is finishing her list of men she's been with; but says that the last man she was with was Ben Donovan, conveniently leaving Dan out. Steven confesses that he feels ready for anything that might be published about her. Sage comes in and tells them Nate will meet them at the show after he's done with work. She also asks Serena to come, and she agrees. Elsewhere outside, Lily calls Bart and tells him that she wants to go to the spa and they should cancel their dinner plans. Bart asks if she's still upset over Chuck spreading the rumors and reveals he's planning to have a talk with him. Lily tells him not to since she already did, and finishes that she'll call him after she's done. After they hang up, Chuck thanks her for keeping things secret and they head off. However, unbeknownst to the three, Bart follows them out of town. When they arrive, Blair pretends to see a woman waving at Lily, and Lily goes over as to not be rude. When she walks away, Blair tells Chuck to run and he asks an employee if any of Sheikh Hassan's horses are competing. The woman answers that only one is, named Crown Jewel. Before Chuck can follow the lead, Lily walks back and asks where they should begin their tour. Elsewhere, Nate arrives and meets up with Serena, Sage, and Steven. Serena and Sage go off to check out the horses and leave Nate and Steven behind to talk. Nate tells Steven that he's a fan of his business and calls him sir. Steven replies that since Nate is dating his daughter and he is dating Nate's ex, there isn't a need for any sirs. They walk off together. Meanwhile, Blair, Chuck, and Lily are about to start their tour when Chuck overhears a voice on the loudspeaker announcing Crown Jewel is leaving the course, as well as he was ridden by the Sheikh's daughter, Iman. Chuck suggests Blair and Lily get a drink while he explores a little on his own. Wanting to distract Lily, Blair takes her by the arm and asks her to introduce her to some women she knows there to get their input on a possible equestrian line. Chuck confronts Iman and compliments her horse, then asks about buying it.
Back in the city, Georgina and Dan are narrowing down finalists from their interviews. Dan admits that none of the girls aren't who he is looking for. Confused, Georgina tells him that finding true love wasn't part of the deal, but he leaves the restaurant anyway. At Stone Orchard, Chuck fishes with Iman, inquiring about a horse he saw compete once named Lady Alexander. She laughs and explains that Lady Alexander was her childhood horse but never competed. Chuck tries again, saying that his father bought her for a lot of money. Iman says again that he is mistaken, since Lady Alexander was sold to a family friend awhile back and put to pasture. She is saying that Lady Alexander was worthless to anyone but her when Bart walks up and finishes that that made her priceless. Iman gives him a hug, while calling him Uncle Bart, and he asks if his son is trying to work his charms on her. Iman asks why Chuck didn't tell her Bart was his father, then adds that their fathers were good friends before her father's accident. Bart expresses his condolences. Meanwhile, Serena introduces Sage to Lily. After they greet each other, Sage goes off to find Steven and Nate. Lily asks Serena how old she is, then realizes she's probably the reason Serena has a father complex. Elsewhere, Nate and Steven are talking sports when Sage comes back. Steven asks where Serena is, and Sage answers that she's with Lily. As Nate is asking if Lily is there, a blast comes in. While Serena and Lily are walking around, Serena reads the blast and discovers that Lily has slept with Steven before. She runs over to Steven and asks why he omitted Lily from his list. Steven denies sleeping with Lily, and Nate jumps in to apologize, saying he didn't know the tip was about Steven since he gave it to his assistant. Angry, Sage walks off and Nate follows. Steven explains that he has no idea why it says he slept with Lily, but Lily comes up and says it is true. She reminds him of a wedding they both attended in an Irish castle, where they snuck down to the dungeon and did it after having the oldest bottle of whiskey they could find, and that her name was Lily Mueller then. He recognizes the name and realizes she's right. He explains that it was right after he got divorced and that he was on a lot of painkillers at the time, plus being drunk. Serena yells that she knew that she was dating him but never said anything. Lily replies that she didn't know what to say and she thought Steven should tell her. Serena stalks off.
Elsewhere, Bart asks Chuck what he was doing talking to Iman. Chuck says that Lily would hate to discover that Bart had him followed, and Bart tells him to keep his nose out of where it doesn't belong and to leave Lily alone. Meanwhile, Nate tells Sage he pulled the story off The Spectator and that he got the name off of an old list Lily made. Sage says Steven was starting to like him, then asks what he has against Lily. Nate admits that it was a desperate move to save The Spectator but it was a mistake, and that he thinks he has another option he can execute without hurting anyone he cares about. Back near the course, Blair tells Chuck she saw Lily leave with Bart. Chuck sadly explains that Iman won't talk to him about anything because she's close with Bart. He asks if she's ready to leave but Blair says she needs to use the restroom and she'll meet him at the car. When he walks away, Blair spots Iman and confronts her. She introduces herself and then encourages her to check out what exactly happened to Lady Alexander, and to understand that Chuck is the good guy, not Bart. At Steven's, they arrive back and Serena agrees to try and move past Steven sleeping with Lily. At The Empire, Iman shows up and tells Chuck that she looked into what Blair told her about Bart; and that Lady Alexander never went to a farm in Virginia. Chuck asks if Blair told her that, and Iman admits Bart did. She finishes that no horses from here family can be found anywhere. He asks what her Bart could have possibly been buying then, perhaps a hotel. Iman answers that her father was in the oil business, but that Bart couldn't have been involved with that. Chuck asks why and she explains that the US has an embargo against trading oil from Sudan, and that while they have a home in Dubai, Sudan is their primary residence. Chuck quickly pieces together that if that was indeed what Bart was trading, he was breaking federal law.
At The Spectator, Nate is meeting with an investor. He apologizes for leaving out the numbers from the new market, and the investor agrees that they look better and that with projections like those, they're happy to extend the line of credit. Nate thanks him and leaves to make a copy of the paperwork. While he's gone, the investor calls Bart and asks if he's sure he wants to cosign the loan; since it's clear Nate doctored the earnings report. Bart replies that he wants to sign anyway and hangs up to talk to Lily. She apologizes for not telling him about going with Chuck, and Bart tells her that all Chuck is trying to do is manipulate her to ruin their relationship. He goes her an ultimatum: to either be with Bart and stay away from Chuck, or don't and lose him. Lily replies that he can't ask her to do that since Chuck is her son too. She leaves to take a phone call from Nate. At the Waldorf's, Blair is on the phone with Chuck, who is filling her in on everything. She tells him to turn Bart in, but Chuck says they need evidence. Blair replies that she was already planning their victory celebration, and Chuck tells her to hold onto that thought. When they hang up, she listens to a voicemail from Jean-Pierre telling her that Eleanor knows she's avoiding her calls and she has one month to fix the no buyers problem. At The Empire, Nate is profusely apologizing to Lily about the stories when Sage arrives. She says that if Serena and Lily can forgive, she can too. At the loft, Rufus is putting the boxes out and Ivy explains that she didn't go through all of them yet. Rufus replies that he doesn't want to look back, he just wants to look to their future together. At Steven's, Serena deletes the video of her and Dan from her phone. At Georgina's, she tells Philip to make popcorn because she has a movie to watch, and she opens her laptop to reveal she has a copy of the Serena-Dan video thanks to Serena. At The Empire, Chuck is reading up on sentences on other billionaires also indicted for illegally trading oil. Back at the Waldorf's, Dan arrives and asks for a place to stay. Blair replies that he made it clear he wants nothing to do with her, and he admits he misses her and needs a friend. Blair thinks for a moment and then says that Serena's room is free and he can make himself at home.
- 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
- Michelle Trachtenberg as Georgina Sparks
- Robert John Burke as Bart Bass
- Sofia Black D'Elia as Sage Spence
- Barry Watson as Steven Spence
- Hina Abdullah as Iman Hassan
- Brian Batt as Himself
- Jessica Springsteen as Herself
- Paper and Gun by The Cold and Lovely
- I Can Go by The White Arrows
- Pick & Choose by Stepdad
- Warrior (Jungles, Pt. 2)
Sage: I am dying for an excuse to skip brunch with my dad and Serena van der Floozy.
Chuck (to Blair): I always wanted to commission a portrait of you.
Blair (on Lady Alexander): It says she was sold to Bartholomew Bass for just under a million dollars.
Chuck: Is that a lot of money?
Blair: For regular people, yes.
Dan (to Serena): Do you really think my father or Nate are more interesting than the infamous Serena van der Woodsen?
Ivy: Lily acts so high and mighty but look at her. She's been married a dozen times, had countless affairs, a secret kid, she's even spent time under house arrest but never pays the price.
Chuck: I find the company of animals preferable to some people.
Blair (on Bart): He isn't exactly a big donator of PETA if you know what I mean.
Iman: I'm not sure I do.
Blair: Bart Bass. Killed a tiger on safari, eats veal on a regular basis!
Iman: I don't know about any of that, but he was a good friend to my father. He bought Lady Alexander and the others so they could live out their days on a farm in Virginia.
Blair: Okay, listen, Princess Jasmine. The fact is, your "Uncle Bart" is bad. I'm sure every horse he bought from your family went straight to the glue factory, including your beloved Lady Alexander. But, if you like, go ahead, check it out. See if you find the Bart Bass Home for Antiquated Equines. Trust me, Chuck is the good guy here, and he needs your help.
- The episode title is based off the movie The Portrait of a Lady.
- This is the third time Lily's list of people she's been with has gotten her in trouble. The first time is when she lied about the length of it when she first made it (The Grandfather), the second when Rufus found out she slept with Russell Thorpe (The Kids Are Not Alright), and the third being in this episode.
- The night mentioned in the letter from Lily to Rufus about their passionate night together was the night before her wedding to Bart Bass (Much 'I Do' About Nothing).
- The episode was originally supposed to air on October 29, 2012, but was postponed due to Hurricane Sandy.
Golden Boy Can't Buy a Break
He has been called playboy, party boy, pretty boy and golden boy - a man with the social pedigree, megawatt smile, and enviable lacrosse skills of one of Manhattan's chosen ones.
Nate Archibald has the opposite of The Midas Touch. Instead of everything he touches turning to gold, he turns all the gold he's been given to dust. Consider his helming of New York newspaper The Spectator which had shown promise but is now, under his leadership, a third-rate gossip rag known for being scooped rather than doing the scooping. Nate would never admit it, but the publication is under serious financial strain. I guess the problem with being born with a silver spoon is that you only know how to have money - not make it.
Nate did not earn his position of power at The Spectator by slogging through tough years of beat reporting, or making a daunting climb up the publishing ladder. He literally slept his way - not to the top, more just at the top - when he got it.