The Waldorfs are a wealthy family that live in a penthouse on the Upper East Side. The members are Eleanor, Harold, and Blair Waldorf. Roman could also count as a member of the family as he is Harold's new life partner. However, only Blair and Eleanor live in the penthouse, as Harold divorced Eleanor to live with Roman in France. Eleanor got remarried to Cyrus Rose, who is a step-father to Blair.

Season One Edit

In Pilot, the Waldorf Family is first seen when Eleanor is hosting a party. Harold has already left New York, and Blair is a junior at Constance Billard School for Girls. She comments on Blair wearing one of her dresses from Waldorf Designs, and says that the size isn't perfect for Blair. She then refers to Blair as her best advertisement. At the party, Eleanor is the first to notice Serena van der Woodsen at the party, marking her official return to New York. When meeting for drinks with Serena later in the episode, Blair mentions that Eleanor lost 15 pounds and got an eye lift after Harold left. Serena briefly references Eleanor's country house although this is never mentioned in the series again. When getting dressed for the Kiss on the Lips party, Eleanor tells Blair that she will never be more beautiful or thin or happy as she is now and she wants her to make the most of it.

In The Wild Brunch, Eleanor leaves a dress for Blair to wear to Bart Bass' annual brunch along with a note saying she went to Paris. Later, Jenny drops by and Blair tries the dress on only to decide she doesn't like it. She gives the dress to Jenny and in Gossip Girl's closing monologue, she says that an Eleanor Waldorf original is the staple uniform of Blair's private army.

It's Ivy Week at Constance/St. Jude's in Poison Ivy. This is the first episode that features Dorota as a motherly figure to Blair, as Eleanor is still in Paris. Blair and Serena are at a war which only comes to an end when Blair reads a letter she wrote to Serena while she was still at boarding school. She mentions Harold leaving the family for a 31 year old male model, Roman Garrel in the letter.

In Bad News Blair, Eleanor returns from Paris. Blair, not aware that Eleanor is home, is surprised to find her downstairs with Serena one morning. She announces Bendel's is interested in carrying her line and it may be the beginning of a new lifestyle collection. She isn't very loving towards Blair, telling her to have a low fat yogurt over a croissant and pushing her to the side to discuss her collection with Serena. When Blair and Serena return from shopping, Eleanor is meeting with her employee Laurel on possible models for the collection. Eleanor originally wanted a girl from the high fashion look book, but Laurel is convinced that the line needs a fresh new face, someone now and hip. Eleanor refers to Blair as her first dress form, and the women decide that Blair should be the face of Waldorf for Bendel's. At the test shoot later that night, Blair's poses are uptight and conservative. The photographer tells Laurel that Blair is too stiff and unnatural. Serena overhears the conversation, and is able to get Blair to loosen up for the camera. In helping Blair, she stands Dan up for their date. At home that night, Eleanor tucks Blair in bed and tells her that she looked beautiful and Blair is visibly happy she made Eleanor proud. Afterwards, Laurel and the photographer go to see Eleanor at the Waldorf penthouse. They show Eleanor the photos, and that they don't think Blair is the right girl. They reason with her that Blair is too unapproachable, controlled, and perfect, not what Eleanor wants the model to say about the line. Eleanor argues that Blair is not unapproachable but poised and regal. The photographer says that Blair lacks the ability to achieve symbiosis due to her rigid appearance. They suggest Serena is warm and fun, and will show clients that if they buy the clothes, they too will have fun. Eleanor decides to go with Serena. The next morning, Eleanor tells Blair that the photographer decided to go in a different direction and hire a different model, but leaves out that the model is Serena. She tells Blair that they will have dinner together that night, and Blair is disappointed, but doesn't let her mother see. After Eleanor leaves, she calls Serena and leaves her a message saying they should crash the shoot and see who they replaced her with. When she arrives at the location, Blair finds that Serena is her replacement and the two argue over it. Serena then goes and tells Eleanor she quits, but Eleanor tries to get her to stay by saying Blair would understand when she explains it. Dan is also at the shoot, invited by Serena as a make up date for the night before, and tells Serena he doesn't understand why she was the star when Blair was supposed to be. She replies by saying that Eleanor tricked her into coming because she didn't want Blair, and how are you supposed to tell your best friend that? He leaves Serena and finds Blair sitting in a hallway alone. He explains how his mom left but Rufus and Jenny don't see it. He tells Blair that he has so much to say to her, but doesn't go through with it every time he has the chance. Blair asks why, and he responds that he wishes he had because at least then she would know how he felt. As a result, Blair confronts Eleanor and asks if she chose Serena over her. Eleanor says she was going to tell her, and that there was no right decision or time. She admits that it was mishandled, but Blair thinks Eleanor is just trying to get her to agree with her. She tells Blair that Bendel's will take her company to the next level, and she deserves to be there; and if Blair had messed the deal up, she would have never been able to forgive herself. Blair replies that she hopes she never does and leaves. Blair meets up with Serena on the roof and the two make up. Blair admits that the day was important for her. As revenge, the two girls steal Eleanor's collection and take pictures around the city together.

In Dare Devil, during a game of Truth or Dare, Blair locks Jenny in Eleanor's store, although the shop is never seen or mentioned again.

Eleanor is celebrating the success of her Bendel's deal in The Handmaiden's Tale. Serena mentions to Lily that the Waldorf women tend to go all out for events. Howard Archibald, The Captain, petitions Eleanor to let him bring her company stock public. Eleanor however, is in contact with Calvin Klein's people and wants to let seasoned professionals handle the deal. Anne Archibald tells Eleanor that when Nate and Blair get engaged, she thinks he should give her her great grandmother's ring, the same one Cornelius Vanderbilt gave her. After the masked ball, Nate comes home to the news that Eleanor decided to let The Captain take his company public.

Eleanor is having the Archibald's over for dinner to celebrate the deal in Victor Victrola. She picks a dress for Blair to wear, and tells her about how Anne showed her the family ring and Blair gets excited, thinking Nate is planning to have her in his future long term. Before the dinner, Jenny tells Blair that Nate kissed her at the masked ball and told her he still had feelings for Serena. When the Archibald's arrive, Blair is cold towards Nate. While they are all sitting together, The Captain and Eleanor pressure Blair into trying on Anne's ring.

After The Captain's arrest for embezzlement and fraud, Eleanor is very upset because the contracts for their deal are about to be drawn in Seventeen Candles. She calls her lawyers to put a stop to the deal, but Blair is more concerned for Nate and his emotional state. Meanwhile at the Archibald home, Anne tries to get Nate to give Blair her ring, to ensure her and Eleanor's loyalty. He calls Blair to say they may have taken their break up too hastily, and maybe they should get back together, but only to help his family; although he leaves that part out. Blair is over the moon. Nate goes to see Chuck, and confides in him that Anne is trying to get him and Blair back together to get Eleanor's support by not backing out of the deal. Chuck tells him not to cave to his parent's wishes if getting back with Blair is not what he wants. Later outside Blair's birthday party, he runs into Jenny and goes for a walk with her instead of going upstairs. At the party, Chuck accidentally on purpose drops the ball that Nate is pretending to like her to use her to get Eleanor's support. Outside, Nate tells Jenny that he was only going to give Blair the ring to help his family but that he doesn't want to, because his dishonesty isn't fair to either of them. Blair tells everyone that they broke up, and that he was only going to get back together with her so Eleanor would help his family. Nate goes home and tells his parents that it's over and he isn't going to do what they want anymore, including giving Blair a ring to ensure the Waldorf's loyalty.

It's Thanksgiving in Blair Waldorf Must Pie and Blair is super excited to see her dad for the holiday. In a flashback to Thanksgiving the year before, Blair is a newly recovering bulimic, Harold and Eleanor are still married, and the Waldorf family seems happy. This is the earliest mention of Roman, as Laurel is bringing him to the dinner. It's also alluded to that Harold has cheated on Eleanor with models before. Back in present day, Eleanor is having a catered Thanksgiving dinner. She tells Blair that Harold isn't coming to dinner, as he decided to stay in Paris because he was too swamped in work. Blair is confused, and wonders aloud why he wouldn't tell her himself. Eleanor replies that she should know by now that Harold is not a fan of difficult conversations. Upstairs, Dorota is helping Blair get dressed for dinner. She vents about Harold not calling her, and Dorota tells her to call him, and maybe he will tell her the real story. Later during dinner, Eleanor asks Blair why she isn't eating. Blair confronts her about calling Harold and telling him Blair didn't want to see him, that she didn't want to talk to him because she was so angry at him, and about uninviting him. She tells Eleanor that Harold didn't leave them, he left her. Eleanor replies by telling Blair to either eat or leave the table. Blair also notices that Harold's famous pie is missing, and Eleanor tells her she had it sent down to the doorman to make room for the catered desserts. Blair then goes to the kitchen and eats an entire dessert before purging, relapsing for a moment to her bulimic habits. Afterwards, she calls Serena, who comes over, and Blair expresses her anger towards Eleanor. Later when Blair returns home after leaving with Serena, Eleanor tells her the real reason she uninvited Harold was because he had had divorce papers sent. Blair tells her that since he's living in Europe with a man she can't be all that surprised, and Eleanor admits that she's not surprised at the papers but by her feelings about them. She tells Blair that she couldn't face him at their happiest time, the holidays. Blair asks why she didn't just tell her, and Eleanor sadly tells her that if given the choice, Blair would have chosen her father. In response, Blair gives her a hug. In another flashback to last year's Thanksgiving, all three members of the Waldorf family are shown hanging out together, happy. In present day as the episode ends, Blair and Eleanor are shown having tea and cookies while talking together.

In Roman Holiday, it's almost Christmas, and Harold is returning to New York for the first time since he left. Blair is very excited, and buys two huge candy canes at Constance/St. Jude's holiday bazaar, as it's their father/daughter tradition. She tells Serena that she will spend Christmas Eve with Harold, but Eleanor decided to have Christmas Day with only herself, Blair, and Dorota. She also tells Serena that she is planning on convincing Harold to move back to the city, since she thinks Roman is just a phase. When she arrives back at the penthouse, Blair is disappointed to find Roman there with her father. She grudgingly gives Roman her giant candy cane. Eleanor is also slightly annoyed at Roman being there. The next day, Blair, Eleanor, Harold, and Roman go to the park to ice skate. When walking together, Harold tells Blair that he bought a chateau in France with Roman. Eleanor is approached by a man, who plays dumb and asks where the skating rink is. Roman tells Eleanor he was flirting with her, but Eleanor doesn't believe it. When they arrive at the rink, Eleanor leaves to go to a meeting and Roman decides to skate with Blair and Harold. When they start skating, Blair stands on the sidelines while Harold and Roman skate together. Roman, not knowing how to skate, attempts to skate towards Blair. When he reaches her, she sticks her foot out and Roman trips and injures himself. In the elevator back at their apartment building, Blair is annoyed that Harold skipped tea to be with Roman at the ER and that Roman comes off as innocent although he stole Harold away from his family. Eleanor explains that Roman was not always innocent, that once upon a time he was dating a horrible scoundrel named Freddy. Eleanor warns her not to mention Freddy to Harold, because it's a sore subject. Later, Blair invites Serena over to ask if she still has a modeling log in since she did a print ad once. She is able to get in, and Blair is able to find Freddy's contact information. At Eleanor's Christmas party, the man who flirted with Eleanor at the park comes. He introduces himself as Jack to Eleanor and tells her that Roman invited him. She confronts Roman about inviting strangers to her party, and Roman informs her that his name is Jack Roth and he owns a prominent hedge fund with offices in London and Barcelona, and is very attracted to Eleanor. She is annoyed, and tells him that she is doing just fine without his romantic help. He tells her that they've been friends for a long time, and she replies that friends don't steal other friend's husbands. Soon after, Freddy shows up, much to the surprise of Eleanor, Harold, and Roman. He tells them that Roman invited him, but Roman denies it. Harold believes Freddy, and Roman gets upset that Harold doesn't believe him. Eleanor catches a glimpse of Blair, and she figures out it must have been Blair who invited him. She tells Freddy that if he wants to be the featured in her spring catalogue, he better tell the truth. He admits that Blair offered to buy him a cruise and renew his gym membership. Eleanor tells him that he might as well take that cruise, since he'll be in her catalogue when hell freezes over before telling him to leave, which he does. Harold is confused at why Blair would do something so mean to Roman, who has always been nice to her. Eleanor tells her that Blair is angry at Harold for bringing Roman, since he showed up with Harold without even the courtesy of a heads up. Harold tells Eleanor that he hoped if they were forced together, they would get along. Eleanor tells him that Blair learned scheming from her mother and unrealistic dreaming from her father, and that while Blair tries to act grown up, she still needs her daddy. Later upstairs, Harold comes to talk to Blair. He asks for forgiveness for not telling her about Roman coming and that he had hoped Blair would love him too. Blair says that she was going to convince Harold to move back to New York, and sarcastically asks about a commitment ceremony, to which Harold admits to. She also confides that she's scared that now that he is living somewhere else with someone else, there's no room for her in his life anymore. Harold assures her that no matter what, there will always be room for her. He then shows Blair a DVD of his home in France, which includes a room decorated just for her, and a cat named Cat like in her favorite movie (Breakfast at Tiffany's) and that he hopes she will spend the whole summer with them. The next morning, it has begun snowing. Eleanor comes downstairs with Jack, as the two of them had spent the night together, although Jack is never seen again. Harold and Roman show up again, their flight having been cancelled due to the snow. Eleanor tells the two that they can stay at the penthouse. Blair comes downstairs, and excitedly tells Roman that he is in for a treat, since a Waldorf Christmas is like no other. They all take a picture together after the gifts are opened.

In A Thin Line Between Chuck and Nate, Blair thinks she might be pregnant but isn't sure who the father would be: Chuck or Nate. Serena buys tests for her to take, but Blair, being in a good place in a new relationship with Nate, refuses to crush her happiness. Serena goes to see Chuck, where she finds out Blair also slept with Nate and hadn't told her. She goes to see Blair at her penthouse and asks her about it. The two argue, and Eleanor walks in on it. She asks what's going on, and gets no answer from Serena or Blair. She admits to Blair that she suspects Blair's bulimia might be back, as she heard her making herself throw up. She tells her that maybe she needs to take a break and go see Harold in France, but Blair says she's fine and Eleanor leaves the room. After, she takes the test and finds out she's not pregnant. Outside of school, Blair blows off Chuck, and he gets angry. In retaliation, he tips off Gossip Girl that Serena was never pregnant and that Blair slept with two guys in one week. At school, Nate reads the blast and assumes it's not true. He runs into Jenny, who is also angry at Blair, and she confirms that it's true, having overheard Serena tell Dan the night before. Blair reads the blast and desperately looks for Nate, eventually waiting for him at his house. When he arrives, he tells Blair off before breaking up with her. Blair goes home and calls Serena over. She yells at her about telling the Humphrey's, which Serena eventually confesses to. Blair tells her that she's a Waldorf, and can't throw her reputation away, like Serena already has. Serena tells her that since her reputation means so much to her, she can weather the storm alone with the Waldorf family name. The next day, Blair is dethroned by her own minions, including Jenny. She goes to see Chuck, who also rejects her. Eventually, she goes home where Eleanor tells her that she is very concerned. Blair tells her she will be okay if she goes to school for a semester in France. Eleanor says that Harold was thrilled about the possibility of a visit, and Blair begs to go. Eleanor promises Blair that she will get her a flight out the next day. However, later that night, Serena finds Blair about to leave and convinces her not to leave the city.

Season Two Edit

Blair returns to the US in Summer, Kind of Wonderful. She brings along her new boyfriend Marcus Beaton, although she knows him as James at this point. When prompted by Chuck, he tells how him and Blair spent time with Harold, Roman, and Cat at their chateau in France.

Eleanor returns home in The Dark Night. Serena asks Blair if she's excited for her mother to meet Marcus, although Blair doesn't give a straight answer. Jenny has been interning at Waldorf Designs and has been waiting to meet Eleanor and get her to look at her designs all summer. Laurel mentions how she is planning on meeting Eleanor at the Waldorf penthouse because of Blair's party. However, Eleanor shows up at the atelier unexpectedly and overhears Jenny's inappropriate comments on one of her dresses. Jenny profusely apologizes but Eleanor tells her she needs people working for her that she can trust, and fires her. Later that evening, there is a city wide blackout and Jenny has finished clearing her station out and tells Eleanor that she's leaving. Eleanor tells her that she can stay until the lights come on, and the two begin to work together. Eleanor confides in Jenny that she spent the summer traveling to the stores and boutiques that carry her clothes, and that she felt like a fat cheerleader and is fearful of becoming irrelevant. Jenny apologizes again, and tells Eleanor that the first designer dress she ever bought was one of her designs; and that it was one of the first things that made her want to become a designer. The lights come back on, and the two are so hard at work Eleanor doesn't even notice. Rufus shows at the atelier with his date to make sure Jenny was okay, and it occurs to Eleanor to call Blair and make sure she's okay. Jenny goes to leave with Rufus, but Eleanor tells her she can't since they haven't finished designing the dress yet. She mentions that she was fired, but Eleanor tells her not to be so dramatic and asks if Rufus and his date could bring them sandwiches and coffee since they'll be working pretty late. This begins the business relationship of Jenny and Eleanor, which causes problems with Blair.

In The Serena Also Rises, it's Fashion Week. Jenny has started skipping school to work at Waldorf Designs full time. Blair is designing the seating chart for Eleanor's fashion show, as Eleanor told Laurel that Blair could make a better seating chart than a professional. Eleanor asks if Blair and Serena will be backstage for the show, and Blair says of course, it's the tradition and that she sat her minions in the second row. Eleanor says that's fine and that they'll worship Blair for it. Also, Serena has begun hanging out with socialite Poppy Lifton and is getting a lot of media coverage for it, including a photo in Women's Wear Daily. Blair sees the photo and begins to get jealous. Meanwhile, Eleanor is relying on Jenny a lot at the atelier. Laurel approaches Eleanor, and informs her that the seating chart is weak, that there are no It-Girls there. Eleanor tells Laurel that Blair said that they can't get A-List girls because Marc Jacobs is having his fashion show at the same time, and Laurel frustratingly tells her that they need girls like that because they bring press. Jenny overhears the conversation, and shows Eleanor and Laurel Serena's photo in WWD. Back at the Waldorf penthouse, Blair is venting her anger of Serena and her minions to Dorota when she notices her seating chart is rearranged, and is mad since Eleanor asked her personally to do it. Dorota lets it slip that Jenny changed the chart. When Eleanor comes home, she tells Blair about Jenny's great idea to have Serena and Poppy in the front row. Blair informs Eleanor that there is no way that will work out, since Poppy and her friends never miss Marc Jacobs' show and Serena always watches with Blair. Eleanor replies that it is going to happen, since she already asked Lily and she said yes on Serena's behalf. She then mentions that Jenny has an independent study, but Blair realizes that she can't, as she's only a sophomore. She goes to leave the penthouse where she runs into Jenny and tells her off for ruining her seating chart. At the Van Der Woodsen's, Serena is skeptical that Blair won't be okay with her sitting front row because of their backstage tradition. Lily and Poppy convince her that sitting front row is an honor and she should take Eleanor up on the offer. Blair goes to the Humphrey's loft in Brooklyn, and Rufus answers the door. She presents Rufus with chicken soup, and tells him that Headmistress Queller told her that Jenny hadn't been to school for ten days due to mono. Rufus mentions that Jenny is working with Eleanor that night and he knows Blair isn't interested in Jenny's best interests. Blair gives Rufus her phone and tells him she had Headmistress Queller's phone number and he can call to ask her himself. Once the headmistress confirms it, Rufus goes to see Jenny at the atelier to take her home. Jenny realizes it was Blair who told Rufus when they leave. The next morning, Serena shows at the Waldorf's to ask Blair to hang out with her and Poppy. Blair tells her that it's wrong of her to disregard their oldest tradition to go to Eleanor's show with a complete stranger. Serena argues that Eleanor asked her to, and Blair asks how she could not possibly disappoint Eleanor but have no qualms over screwing her best friend over. Serena threatens to not go, which Blair is fine with, but then tells her that if she doesn't go, neither will Poppy, and Blair can explain to Eleanor why she has an empty front row. Finally, she decides to go and leaves. At the fashion show, Blair has Serena's seat moved to the back. Jenny, having ditched out early on her meeting with Headmistress Queller, shows up and helps Serena tell an employee that the name on the seat is wrong. Eleanor also shows up and realizes Blair orchestrated the change. She asks Blair what's wrong with her and to spare the dramatics for one night. She then blows Blair off by telling her not to get underfoot, at the same time telling Jenny how happy she is to have her there. A jealous Blair sabotages Jenny's job of making sure the models get to the runway by sending them all home. Jenny then has the idea to have Serena, Poppy, and their socialite friends to walk in the show instead. Eleanor is at first turned off by the idea, but then Laurel convinces her by telling her that the socialites saving the show will bring a lot of press. Backstage, Blair is still mad at Serena and Jenny and gives her the dress Jenny was planning on wearing to the after party to wear on the runway. Eleanor sees Serena wearing the dress, and Jenny admits to her that it's one of her designs. After, she confronts Blair about why she did it and tells her that there's a reason she wanted to be friends with Blair the year before. When Eleanor threatens to expose Jenny sneaking her dress into the show, Laurel tells her that Andre Leon Talley loved the finale dress. Blair comes to Jenny's defense and tells Eleanor that it was her idea to use socialites and she saved the show. Jenny begs Eleanor to take credit, which she eventually decides to do.

Blair is going to Yale University for a visit in New Haven Can Wait. Dorota mentions how Blair used to sleep in Harold's Yale sweatshirt when she was little. At the Dean's private party, Blair introduces herself to Harold's old favorite teacher.

In There Might be Blood, Blair is babysitting the daughter of a wealthy Yale donor named Emma. After a long night spent chasing her down, the two talk. She admits to Emma that she wrote the book on distracted self centered mothers. She tells her that Eleanor has never met any of her teachers, she regularly forgets her birthday, and only mentions her appearance when she has something to criticize.

It's Blair's eighteenth birthday in Bonfire of the Vanity, and Eleanor is planning introduce her new boyfriend to Blair beforehand. Blair excitedly tells her friends that Cyrus Rose was one of Eleanor's divorce attorneys and he asked her out multiple times until finally she said yes and they fell in love. Eleanor tells Blair that Cyrus is the most attractive and brilliant man she has ever met and that Blair is going to love him. When Cyrus shows at the penthouse, Blair is turned off and very disappointed. The next day, Blair tells Serena that Cyrus is totally unsuitable for Eleanor, and that she wanted a Cary Grant but got a Danny Devito. When party planning with Eleanor, Cyrus announces that he is taking her to see Cyndi Lauper the next evening so they will be gone for the party. Blair informs the two that she has changed her party to an adult party and she wants her mother to be there. Cyrus says he'll return the tickets but Eleanor insists on going. The next morning, Dorota comments on Eleanor's love glow. Blair asks how she could possibly love Cyrus, since he does everything she hates: including using the wrong fork, slurping his soup, wearing sports socks, and being short and pushy. She also tells Eleanor that he is nothing like Harold, and Eleanor admits that's why she likes him. She tells Blair that while Harold was amazing in a lot of ways, he also had faults. After she leaves, Blair invites Cyrus to lunch to see if she can dig up a big secret. At lunch, Cyrus says that Eleanor is a diamond in an ocean of coal and the moment they met, he knew she was the one. Blair asks about his past loves, and Cyrus admits to falling in love with a woman overseas when he was drafted to Vietnam and cheating on his first wife, Alice. But when Cyrus went back to America to end his marriage, Kim Li, the other woman, was killed in an attack on her village. He tells Blair that he always wanted to find a deep love like he had with Kim Li again, and he found that in Eleanor. When Blair is getting ready for her party, she is confronted by Eleanor for trying to dig up dirt on Cyrus. Eleanor accuses her of being an immature schemer, and Blair tells her that Cyrus is just like Harold; cheating on his first wife and falling in love with the other person. Eleanor is upset and leaves Blair's room. Meanwhile, Serena has been dating Aaron Rose, and when she meets Cyrus as Blair's party, she finds out that he's Aaron's father. Eleanor then comes downstairs and demands to know if it's true that Cyrus cheated on his first wife. He admits to it and she kicks him out. She sadly tells Blair she thought he was different and goes to lie down. Right after he leaves, Cyndi Lauper shows up and informs Blair that Cyrus bought out her gig and asked her to play Blair's birthday instead. Outside the apartment building, Blair catches up with Cyrus and finds he outmaneuvered her by letting her win and having Cyndi Lauper prey on her emotions. She tells Cyrus he better be good to Eleanor or she'd be coming for him, and asks him to come upstairs with her to tell Eleanor the whole truth, since she'll be so angry she might need an attorney. Cyrus hugs Blair and they each tell the other they weren't what they had in mind. The next day while talking to Serena, Blair finds out Aaron is Cyrus' son and that she is okay with Cyrus now, since she won't have to see him that often. However, that is before she finds out that Cyrus is moving into the penthouse that day.

It's Thanksgiving in The Magnificent Archibalds, and Blair is disappointed when Cyrus and his family bring new traditions to the holiday. The Rose family has a restaurant Thanksgiving and are very different from the Waldorf's, plus Harold isn't coming. Blair and Dorota still make Harold's pumpkin pie, but when she comes downstairs later that night, she finds Cyrus eating it. She asks Eleanor why she is letting Cyrus ruin Thanksgiving, and Eleanor replies that Cyrus made reservations at Blair's favorite restaurant and is having the chef make her favorite recipes, and she needs to understand that he is a part of the family now. On her way upstairs, Dorota shows her Eleanor's engagement ring, since Cyrus had proposed that night and they are planning to tell the whole family on Thanksgiving. The next day, Blair tells Eleanor that her not telling Blair her secret is wrong. Eleanor says she has no idea what Blair is talking about, and Blair decides to leave with Dorota. Later, Eleanor and Cyrus are trying to find Blair but are having no luck. Serena shows at the penthouse to see Aaron, and is able to reach Blair and find where her and Dorota are. Meanwhile Jenny is not living at home with Rufus, and instead crashing at the Van Der Woodsen's. When Rufus finds out, she leaves and runs into Blair on the street. She explains the situation to Blair, who tells her that she's lucky to have a family who fights for her; since her's doesn't care if she's there or not. Jenny tells her that Eleanor loves her in her own way, but Blair admits that neither of her parents love her the way Rufus loves Jenny, and that while Harold is sweet, he isn't there for her. At that moment, Eleanor pulls up to take Blair home. When they arrive back home, Blair discovers that the surprise is that Harold has come for Thanksgiving with his famous pie. However, Blair is confused since she thought Eleanor and Cyrus were getting engaged, and Eleanor explains that Harold had to meet Cyrus first to approve of Blair's new stepfather. Blair decides she's ready for a new tradition.

The Upper East Side is in grief mode after the sudden passing of Bart Bass in O Brother, Where Bart Thou?. Blair is still trying to be okay with Cyrus and Eleanor's engagement, when Eleanor asks how Chuck is doing. Blair admits she doesn't know since he's not answering his texts or phone. Blair says she thinks now is the time for Chuck to be around someone who cares about him, and Eleanor replies that's why her and Cyrus are getting married: so that they can always be around to care for each other and Cyrus agrees. Dorota brings Eleanor an envelope with stuff for her trip to Paris, and Blair asks how she can be thinking of a vacation when they're about to bury Bart. Cyrus replies that in the midst of death, they are in life, to which Eleanor agrees. After the funeral, Blair, Nate, and Chuck arrive at the Van Der Woodsen penthouse for the reception. Eleanor and Cyrus are also at the reception and Cyrus remarks on how thought provoking the service was, how it touched on life and death and time being so fleeting. Cyrus tells Eleanor he wants to get married the next day, but both Eleanor and Blair say that that's crazy. However, Eleanor eventually begins to come around but says she doesn't have anything to wear. Jenny, who left Waldorf Designs after a fight with Eleanor in Pret-a-Poor-J, overhears and volunteers herself to make Eleanor a skirt/jacket outfit. They begin to make plans to get married the next evening at their apartment. After a confrontation with Lily, Chuck leaves the reception but is stopped by Blair. She tells him she loves him but he takes off without saying it back. The next day, Cyrus tells Blair how happy he is to have Blair as his stepdaughter and that he loves her. Blair breaks down in tears over Chuck and hugs Cyrus, who comforts her. Eleanor sees and is happy the two are bonding. Eleanor and Cyrus are married that night in front of Blair, Serena, Dorota, and Aaron and officially become the Waldorf-Rose's. Dorota informs Blair that Chuck is waiting upstairs in her bedroom during the toast. She goes and comforts him, but he takes off in the middle of the night and leaves a note for Blair.

It's finally the day Yale releases it's early acceptances and Harold and Roman come to town in You've Got Yale!. They plan a breakfast with a blue theme, Yale's color, and introduce her to a new bulldog, Yale's mascot, named Handsome Dan. Blair drops the "Dan" part of the name and decides to just call him Handsome. The three look forward to the opera later that night. At school, Blair finds out that she was wait listed at Yale. She blames new teacher Rachel Carr, who gave her a B on a paper. After meeting with Headmistress Queller, she learns one girl from Constance got in and her transcript is nearly perfect. Serena gives up her acceptance to Blair, but she decides to get revenge on Ms. Carr anyway. She calls her and asks her out to dinner at The Boathouse and to come to the opera that night, and while hesitant at first, Ms. Carr agrees. At the opera with Harold and Roman, Blair receives a call from Headmistress Queller that she confirmed with Ms. Carr that so long as everything else was up to Blair's usual high standard, she would end with an A in the class. Feeling guilty, Blair leaves to go meet with Ms. Carr. She does, and apologizes to her. However, Ms. Carr calls and tells Headmistress Queller anyway. The next day, she meets with Blair and tells her that she has detention and has already informed Yale, who has put her acceptance on hold.

Blair has early morning trash pick up as her detention in Carrnal Knowledge. At the park, Harold and Handsome bring Blair breakfast. He tells Blair that he wishes she had let her talk to the school, since it seems as if Ms. Carr has had it out for Blair from the beginning. She says she wanted to solve the problem herself, and Harold says it's a mark of maturity. When he leaves, Dorota tells her that her martyr act is no good. At school that morning, Headmistress Queller tells the school that they are implementing a new no cell phone policy during school hours. Blair and her minions figure it was Ms. Carr who helped create the policy, and they decide to take her down. Blair has Dorota sneak phones into the school and tells her minions to dig up any and all information on Ms. Carr to help run her out of town. After searching for a long time, they find no dirt on her and Blair tells them to just make something up then. In the hall, she sees Dan acting nervously around Ms. Carr and she tips off Gossip Girl that they might have more than a teacher-student relationship. Dan and Serena have recently gotten back together, and she confronts him about the rumor. He denies it, and figures out Blair must have been the one who sent the tip. He corners her in the bathroom and tells her that Ms. Carr cares about her students and job but Blair blows him off. Outside, Serena catches up with Ms. Carr and lets it slip accidentally that a rumor about her and Dan is being spread on Gossip Girl. Blair is called into Headmistress Queller's office, where she is met by the headmistress and Ms. Carr. Queller tells Blair that the school is aware of GG but have turned a blind eye since a teacher was never the subject. However, they have to pay attention now since a teacher is a target. Queller asks her secretary to send the student who was a witness to Blair sending the tip, and she fully expects to see Dan but is surprised to find Nelly Yuki come in instead. Nelly tells her that it was either her record or Blair's and she has to go Ivy League. Headmistress Queller then informs Blair that her actions threatened the integrity of the school and expels her. The next morning, Harold tells Blair that Queller is standing firm on the expulsion and Blair replies that Yale will revoke her acceptance as soon as they receive word. Harold also says that if Blair really did start the rumor, Ms. Carr has a legitimate case for slander and he needs to know if she did spread the rumor. Blair admits to spreading it but anything she said wass the truth and she didn't lie. Harold then remarks that the real issue isn't teenagers gossiping online, but a teacher having an inappropriate relationship with a student. He continues by telling Blair that he's going to call his lawyers and fight it. Blair gives Handsome to Dorota and says to give him to a homeless man, but later she tells her to get him back. The Parent's Council calls an emergency meeting that evening to discuss the rumor, and Rufus, Lily, and Harold attend. Serena goes to see Ms. Carr in the park and begs her to take mercy on Blair because she'll lose Yale. Ms. Carr refuses but when she leaves, she accidentally leaves her day planner on the bench. Serena takes it and goes to meet Ms. Carr at her appointment before the meeting to give it back. At the meeting, Harold and Rufus meet but are slightly hostile, as Harold thinks Blair is being horribly scapegoated and Rufus doesn't want anyone else slandered by Blair. When Serena gets to Ms. Carr's meeting, she sees Dan having dinner with her and giving her a hug. Upset, she takes a picture and brings it to Blair. She tells Blair she was right all along, and shows Blair the picture. They rush to Constance to crash the meeting. Meanwhile, Harold is telling the parents that it's a freedom of speech issue because the school doesn't have the right to control what the students do online. Rufus argues that what Blair wrote was slander and she deserves to be held accountable. Another parent chimes in that if slander is the issue, they can seek an injunction against GG and get the site shut down. Lily responds that if they do that, a hundred more sites will pop up in it's place. At this point, Blair bursts in and tells Queller to check her email. She obliges and the picture of Dan and Ms. Carr is shown on the presentation screen. After the meeting, Serena and Dan learn that the parents decided to fire Ms. Carr. Blair shows up and Dan tells her that what she did, using a picture to defend a lie, was wrong. Blair replies that it's not a lie, but eerily prophetic. Harold overhears and realizes Blair was lying the whole time. The next day, Harold is preparing to go home to France. Blair says he should be happy, since she was back at Constance and going to Yale. Harold tells Blair that he saw a different side of her the night before and was disappointed in her. Blair says that she was right, but Harold replies that she was just lucky and allowed him to defend a lie that she was able to look into his eyes and tell. He asks why, and Blair says that she did it to make sure she gets into Yale. Harold tells her that it doesn't matter what college she goes to, what really matters is the person she turns out to be. She asks to take him to the airport, but Harold refuses and says he'll call when he lands because they both have a lot to think about.

In Seder Anything, Blair has already learned that she will not be attending Yale. However, she is looking forward to attending Tripp and Maureen van der Bilt's wedding with Nate, whom she has recently gotten back together with. She is missing Cyrus' Passover Seder to attend the rehearsal dinner and is meeting Nate first. Eleanor tells Blair that she needs to get focused on her future, and Blair replies that being a socialite was good enough for First Lady Jackie O. Cyrus chimes in that he has a friend at New York University, who owes him a favor but Blair quickly dismisses the idea and puts down NYU. When she leaves, Eleanor calls out that Waldorf women are not socialites. Meanwhile, Dan is looking for a job to help pay for Yale tuition and ends up serving the Waldorf Seder. He tells Eleanor that he isn't comfortable serving kinishs to Blair, but Eleanor tells him she won't be at the dinner. At the rehearsal, Blair makes a deal with Nate's grandfather William van der Bilt, that she can be a bridesmaid and he will call in a favor at the Junior Committee for the Whitney for her so long as she convinces Nate to go to Yale. At the Seder, Eleanor is starving and becomes increasingly exasperated at the night's events. Blair fails and William tells Nate that Blair sold him out. When she comes home, she goes upstairs with Serena and the two talk. Eleanor comes in and tells Blair someone wants to talk to her, and she goes downstairs where she apologizes to Cyrus for being so snobby about NYU and for missing the Seder.

Blair, Serena, Nate, Chuck, and Dan graduate from Constance/St. Judes in The Goodbye Gossip Girl. When Blair is dressing for Nate's graduation party, Eleanor asks if she's dressing for someone and Blair says yes, someone she hopes will love her the way Cyrus loves Eleanor. Eleanor tells Blair that Cyrus told her how Blair told Chuck how she felt and ran away, and she tells Blair not to let him get away with it.

Season Three Edit

On the day before Thanksgiving in The Treasure of Serena Madre, Eleanor is scheduled to come back to Manhattan to escort Blair back to Paris. Blair suspects that she has a big secret she's going to reveal in a controlled environment, and after asking Harold who didn't say anything, becomes determined to find the secret out. When she arrives home, she goes through the mail and finds a package from Eleanor's estate attorney: she's changing her will. At that moment, Eleanor arrives and dismisses the package before Blair has a chance to look closely at it. Blair attempts multiple times to look at the package, but fails every time. She asks Eleanor if they can stay in the city for Thanksgiving and celebrate with the Van Der Woodsen's, to buy her more time to discover the secret, and Eleanor agrees to ask Lily. While venting her frustrations to Dorota, Blair notices she is holding tightly onto a bag. Dorota says that Eleanor asked her to pick up some private things for her trip. Blair grabs the bag from her and finds a pregnancy test inside, and assumes Eleanor is pregnant. The next day, Blair tries to get confirmation from Eleanor without asking, by offering her unpasteurized cheese and asking Chuck to bring her favorite champagne. Eleanor declines the champagne, which Blair finds odd. At dinner, Blair accuses Eleanor of being pregnant to which Eleanor gives her a surprised look. Down in the lobby, Eleanor finds Blair eating pie alone. Blair demands to know why she is pregnant, since the world doesn't need another Rose. Eleanor tells Blair she is completely off base and not pregnant. She announces that she and Cyrus are moving to Paris full time. Blair is surprised, since Eleanor loves New York so much. Eleanor tells her they found a beautiful penthouse across from Blair's favorite Parisian restaurant, to which Blair is very happy. She apologizes for thinking she was pregnant, and both women are then approached by Vanya and they realize Dorota is the pregnant one. They both go back upstairs, and Blair comforts a newly heartbroken Serena and invites her to come to Paris with her and Eleanor. Both Waldorf women then give Dorota a plate of food to bring down to Vanya, since she is going to have to tell him eventually. They successfully send her off and prepare to leave for the airport. Before they leave, Serena and Chuck, who was also going to go, both cancel and Eleanor and Blair set off alone.

Eleanor returns to New York in The Empire Strikes Jack for a fashion show. She explains to Blair that Mr. Conwell the CEO of Conwell's, the biggest retailer in the country, is flying in from Salt Lake City to see the show and is her first choice to carry Waldorf Designs' new junior line. Blair is repulsed by the idea and Eleanor tells her that high end fashion has fallen on hard time and Mr. Conwell can put her clothes in over 5,000 retail locations. She then tells Blair that her usual crowd of uptown socialites and upper class friends might give Mr. Conwell the wrong idea and instructs Blair to invite some friends from NYU to come to the show. Blair, having made no new friends at NYU, rejects the idea but Eleanor insists on her bringing ten or twenty girls. In The Grandfather: Part II, Blair had met a high end escort named Brandeis, and has Dorota question her about her hourly rates and if she has 30 friends she can pay to come to the show. Blair has Brandeis tell Ed Conwell about how amazing Eleanor's line is, but tells her to refrain from prostituting herself to him. Serena figures out Blair hired escorts and asks why she couldn't have just told Eleanor she has no friends, and Blair doesn't give a clear answer. Blair talks to Mr. Conwell about the line, who informs Blair that his stores will never carry her mother's line. She demands to know why, since it attracts all kind of good clientele. Mr. Conwell says that even prostitutes are attracted, and he doesn't want that kind of clientele. Blair confronts Brandeis about telling Mr. Conwell she was a prostitute but she explains that he doesn't know she is a prostitute, he knows a man named Julian is. She tells Blair that he has plans with Mr. Conwell that night and they hook up every time he comes to town. Blair then chases down Mr. Conwell and blackmails him into looking at Eleanor's line again. She brings him backstage to meet with Eleanor, where he tells her that he would be honored to have Conwell’s be her exclusive retailer. Eleanor is excited until Mr. Conwell tells her that a few alterations need to be made, including dropping the name Eleanor Waldorf from the clothes since it sounds too upper class New York. Eleanor then informs Mr. Conwell that she doesn't think she will be doing business with him after all and he leaves. She tells Blair that she would rather lose the deal than lose herself, and Blair confesses that she has no friends at NYU and that she hired escorts as her friend. She admits that she didn't want Eleanor to be disappointed, but she can't fit in and hates it there. Eleanor hugs her and tells her that one thing that makes Waldorf women so special is that they don't fit in everywhere, and she will find where she does eventually.  

Both Eleanor and Cyrus have returned to the city in The Unblairable Lightness of Being. Meanwhile, Dorota is panicking about her parents coming to America and finding her pregnant and unmarried. Eleanor is concerned about Blair, since she hasn't left her room for days after being traded for Chuck's hotel in Inglorious Bassterds and Nate arrives to talk to Blair. While they talk, Chuck arrives at the penthouse and offers to throw Dorota and Vanya a traditional Polish wedding to get close to Blair again. Later, Cyrus tells Eleanor bought Dorota and Vanya an apartment in Queens. Eleanor hates the idea, and tells him Dorota doesn't need an apartment since she already has a place to live. Cyrus insists that it's the right thing because she's getting married and having a baby, but Eleanor says it's inappropriate since Dorota is just a maid. Cyrus replies that Dorota is family and she practically raised Blair, to which Eleanor takes major offense to. At the wedding, Blair and Chuck are supposed to be the happy couple who escort Dorota and Vanya into the chapel, but Blair breaks down and leaves before they can do so because her and Chuck aren't happy. Dorota catches up with Blair and the two talk. She explains that she came to America to start a new life and luckily she found a new family in the Waldorf's. Eleanor walks in and hears Dorota tell Blair that all she wants for her is happiness and the right love, and sees the two hug. She then tells them to hurry up, since Dorota is about to get married. Once everyone is seated, Eleanor admits to Cyrus that he was right in saying that Dorota is family and that she was scared to admit that anyone could have raised Blair better than she could have. Cyrus tells her she's a great mother, and she replies that she could have been better because some stuff happened before Cyrus came. At the reception, Eleanor and Cyrus present the newlyweds with keys to their new apartment and Eleanor thanks Dorota for everything. Dorota says she always saw her as a mother, and Eleanor says maybe she's more of a big sister to her. 

In Last Tango, Then Paris, Eleanor and Cyrus have once again returned to New York for a visit. Cyrus invites Blair to come back to Paris with them, but she doesn't say yes right away. When Dorota's baby is born, she and Vanya ask Eleanor and Cyrus to be Anastasia's godparents. Blair eventually decides to go back to Paris with Eleanor and Cyrus, and invites Serena to come with her for the whole summer.  

Season Four Edit

Blair has spent the whole summer in Paris with Serena, Eleanor, and Cyrus, and the weekends with Harold and Roman at their chateau. In Belles de Jour, at a Fashion's Night Out luncheon, Lily tells Eleanor that Serena will be attending Columbia in the fall with Blair. Meanwhile, Blair has met Prince Louis Grimaldi and goes on a double date with Serena and Louis' friend Jean Michele. Eleanor calls Blair to tell her about Serena going to Columbia, and the two girls argue but make up soon after.

It's finally Blair's twentieth birthday in War at the Roses. Eleanor has come home from Paris to throw Blair an early birthday party as her and Cyrus have tickets to the Palais Garner and she figured an early party is better than a late one. She remarks how the party will land on Lily and Rufus' first wedding anniversary and gives Blair her birthday present from Cyrus, a signed copy of This I Remember. Both Blair and Eleanor anticipate a glamorous and sophisticated party. Meanwhile, Rufus is sad because Jenny, having been banished by Blair in Last Tango, Then Paris, is unable to make it into the city to celebrate his wedding anniversary. Dan and Eric decide to ask Chuck to help them scheme a way to get her to come back. Also, Nate and Serena have Chuck and Blair negotiate and eventually sign a legally binding peace treaty to ensure no future Bass-Waldorf conflicts. Dan, along with Eric, sends a fake tip to Gossip Girl about Blair hooking up with Jack over the summer. They assume that once Chuck sees the blast, he'll become angry and go to war with Blair again. Dan then heads over to The Empire to accidentally on purpose run into Chuck and propose he call Jenny and offer her protection to one up Blair. However once he gets there, he is surprised to run into Blair who is now friendly with Chuck since they both realized the blast was fake right away. After the three of them talk, Blair invites both Chuck and Dan to her party later that night. Dan asks Nate about the treaty, who leaves the documents for security to pick up and put in the safe, but not before Dan sneaks a peek at it. Back at the Waldorf penthouse, Blair returns home and is approached by Eleanor who tells her that Lily and Rufus are coming and they have to do something special for them. She also tells her that she noticed Chuck was added to the list and they don't need any trouble, but Blair insists he won't cause any problems since they're no longer fighting. Dorota comes over to Blair and Eleanor and shows Blair her dress for the evening, and she makes an inappropriate comment to which Eleanor replies that she picked it out for Blair. At the Van Der Woodsen's, Dan tells Eric about Chuck and Blair's treaty and it's contents. Eric decides it's best not to go through with messing with them and not to take things any further, but Dan goes through anyway. At the party, things seem to be going well until Dan's plan takes place. Guest star and musician Robyn brings along video of a drunken Blair singing karaoke at one of her after parties for a show and they broadcast it to everyone at the party. An embarrassed Blair rushes to turn the TV off but accidentally knocks over a waiter who knocks over guest star Rachel Zoe causing a scene. Blair mistakenly assumes Chuck was responsible and Eleanor reminds her that she told her not to invite him. Blair confronts Chuck and yells at him until Dan steps in and announces he did it because of Jenny. After the party, Eleanor brings Blair the DVD with the video and tells her Robyn gave it to her and swore it was her only copy. Blair is grateful to have the tape, but is still embarrassed. Eleanor assures her that a good party gives people what they don't expect and that nothing around Blair is ever boring. Blair then admits to feeling vulnerable around Chuck, and Eleanor tells her that she shut herself off for a long time after Harold left and became cold and hard. She explains further that she stayed that way until she met Cyrus who taught her that sometimes you have to allow yourself to be weak in order to grow stronger. Blair replies that that sounds good but feels terrible. Eleanor says that she doesn't have to lose the girl inside her to become a strong woman, but to be careful who's around the next time she's let out before going to bed.

Blair has decided she wants to intern for Indra Nooyi in The Kids Are Not Alright. Meanwhile, Eleanor has returned to town and offers Blair an internship position at Waldorf Designs. Blair turns her down, and Penelope mentions how a lot of girls would kill to intern for Eleanor. Dorota receives Indra's itinerary and Blair discovers that Eleanor is dressing Indra for a party later that day. Later, Blair approaches Eleanor and apologizes for being rude earlier and that she wants to take her up on the internship offer. Eleanor agrees and tells Blair that her assignment is to dress and accessorize Patti Blagojevich. Blair says that she must have meant Indra Nooyi, and Eleanor replies that Indra is a huge new client and Blair is just an intern. Eleanor is thrilled that Blair will intern with her. When Eleanor leaves the room, Blair instructs her minions to tell Indra's entourage that her Eleanor Waldorf fitting has been moved up a half hour. Once Blair leaves to meet with Indra for the fitting, Eleanor looks for the dress in the apartment but finds Blair's planning board of Indra and her career. She realizes Blair was using her to get to Indra. At the same time, Blair arrives at Indra's hotel and discovers she is not in her room. She instead finds a note from Eleanor telling Blair she knows what she did. At Russell Thorpe's party that evening, Eleanor confronts Blair and asks why she would jeopardize her business and career to pursue something she thought of in five minutes to become powerful. Blair apologizes for lying, but tells Eleanor that she has to take her career into her own hands or else she will end up having to follow in Eleanor's footsteps. Offended, Eleanor replies that now that she has realized that Blair's games aren't a phase and who she actually is, she doesn't want someone like Blair trying to be like her. She fires Blair. On the way out, Blair talks to Dan and tells him that while the choice to idolize Indra was random, she didn't want to be the next Eleanor. Dan asks why, since Blair loves fashion more than anything and she shouldn't deny that just because it's what her mother does, referencing Blair's fashion police duties at Constance and calling her an evil dictator of taste. Back at the penthouse, Blair tells Eleanor that she was right in accusing Blair of using her. Eleanor tells her not to be sorry, since she's been watching Blair struggle with finding her path and identity and that she hoped she would want to follow hers. She also admits that any self respecting daughter with an egocentric mother would be repelled at the thought of being like her. Blair replies that that's not true, because Eleanor is brilliant, resilient, a businesswoman, and an artist and she would be crazy not to want to be like her. Eleanor responds by telling Blair that she is not a designer, and then Blair interjects with saying she is a dictator of taste instead, to which Eleanor loves and says she wishes there was a way someone could do that for a living. Then she realizes there is and suggests being an editor of a high fashion magazine. Blair agrees and the two plan to strategize the next day.

In The Princesses and the Frog, Blair gets engaged to Louis and she calls Eleanor and Cyrus to tell them the news.

In the wake of Blair's engagement, Eleanor and Cyrus return to New York to throw her and Louis an engagement party in Shattered Bass. In proposing to Blair, Louis has given up his succession to the throne rights and Eleanor mentions how maybe they can fix that at the party. Also, Eleanor is a judge in a Vitamin Water competition for girls to submit designs for shirts and possibly launch someone's career. At the party that evening, Cyrus is conducting research on Princess Sophie and finds that she is an avid ornithologist, just like he is. When Sophie arrives, Eleanor and Cyrus introduce themselves and Cyrus hugs her. However, after talking with Cyrus about Blair, Sophie decides she's impressed with the Waldorf's and tells Blair her and Louis can make their first formal appearance that evening. Cyrus has told Sophie about Blair's job at W Magazine, her straight A average, and her dedication to avian welfare (referencing her feeding ducks at Central Park). Blair says she loved Cyrus right aware, and Eleanor mentions that she really didn't. Cyrus then gives the champagne toast. Earlier, Blair had gone to see Chuck to warn him that Jack Bass was back in town. Louis confronts Blair about it, and tells her that if she's not ready to show all of her life, not to come to the Constance/St. Jude party that evening. Downstairs, Blair voices her concerns to Cyrus, and asks what kind of princess plays sex games, schemes, and dreams herself into old Hollywood movies. Cyrus replies that the only way to know if Louis is the one is to tell him everything, and coming from someone who is in love with a Waldorf woman, even everything is not enough to scare someone off.

Chuck is desperately looking for Blair at the Constance/St. Jude party in The Wrong Goodbye. He asks Eleanor, who informs him that Blair is finally getting her fairytale and he needs to let her go and not ruin things for her. Later, Blair mentions that herself, Louis, Eleanor, and Cyrus are spending the summer in Monaco and on the Principality of Monaco's yacht. At the end of the episode, a shot of a positive pregnancy test is shown in Blair and Serena's shared bathroom.

Season Five Edit

Blair and Louis have returned to New York from Monaco in Yes, Then Zero to plan their wedding. However, planning with their respective mothers is difficult. Blair wants peonies, but Sophie insists she walks down the aisle with carnations. Vogue Paris, which Eleanor sarcastically remarks is the most important thing to happen ever, wants a photo of Blair for their November issue. Sophie then drops the ball that Blair will be wearing her wedding dress, and Blair is upset because picking her own wedding dress is a big deal for her. Later, Dorota tries to tell Blair news that will affect both their futures but Blair doesn't have time to listen. Blair comes downstairs ready for an evening with Louis, and she runs into Eleanor where they briefly converse over Sophie's bossy ways. Blair says that she's a Waldorf woman who needs to have her own voice, and that that voice needs to be heard. Eleanor remarks that sometimes she doesn't know where Blair's strong will comes from, to which Dorota rolls her eyes. The next day, Eleanor finds a book on pregnancy in the pantry and asks Blair if it is hers. Dorota then confesses that she is expecting her second baby and the book is hers, and Blair realizes that was the news she was trying to tell her that would affect their futures. Both Eleanor and Blair hug Dorota and congratulate her. However at the end of the episode, Blair is revealed to be pregnant.

In The Fasting and the Furious, Blair and Louis reveal to their parents that Blair is pregnant. Eleanor is shocked at first, stating Blair is still in college and asking what the record is for the youngest grandmother on the Upper East Side and Cyrus is thrilled. Later, the families sit down to discuss their plans. Blair asks Eleanor to alter her wedding dress to hide her baby bump, to which Eleanor agrees. She explains to Sophie and Beatrice, Louis' sister, that she plans to have the baby at Lenox Hill in New York and to have them attend school at Constance/St. Jude's. Sophie informs Blair that the baby must be born in their wing at Princess Grace Hospital in Monaco and Grimaldi children always attend boarding school in Switzerland. Eleanor says that Sophie cannot plan to dictate every detail in her grandchild's life, since Blair's life and family are in Manhattan. Sophie replies that Louis' are in Monaco. After an argument with Serena, Blair decides to go along with Sophie's wishes and move to Monaco. Meanwhile, Beatrice is scheming to take the throne from Louis and meets with Diana Payne at Eleanor and Cyrus's Yom Kippur dinner and the two make a deal. Eleanor approaches them, and Beatrice reveals that Blair is planning to move to Monaco. Eleanor is surprised at the news, but says Blair can do whatever she wants, that Waldorf women are not afraid to break rules, and that she isn't hurting anyone. She also mentions that it's not like she's signing a legally binding deal, which gives Beatrice an idea. Upstairs, Blair, Cyrus, and Louis are reviewing the legally binding contract Sophie had drawn up regarding the upbringing of the baby. Eleanor arrives and Cyrus fills her in. Blair is ready to sign, but not before Cyrus reads the fine print. He tells Blair that one clause states that she can't take her child anywhere for more than six hours without informing palace security and that she can't go to New York for more than 48 hours at a time and if she breaks any of the rules, she faces the possibility of losing custody of her child to the royal family. Blair and Louis declare that those rules are outrageous.Louis confronts Sophie, who has no idea of the losing custody clause. She admits to having the contract drawn, but not of the clause. She quickly realizes Beatrice snuck it in. She argues with Louis, and once again tries to take away his succession to the throne but he doesn't let her. Later, Eleanor confesses to Blair that she was the one who put the idea of a contract into Beatrice's head due to her bragging about Blair, and how no matter what, she has the ability to stay her own person and that's why she will be a wonderful mother. Blair apologizes for getting engaged and pregnant so young, since that's not what Eleanor wanted for her yet, and Eleanor replies that these things happen when they happen. She tells Blair that that's the first lesson of being a parent, that children don't always do what you want them to do when you want them to do it but you love them anyway. Blair hugs her. Rufus and Lily, who are also at the Yom Kippur dinner, overhear and Lily remarks that she would have never thought she'd hear such good parenting advice from Eleanor Waldorf. Blair admits that she's relieved that she doesn't have to spend her whole life on one square mile of jagged coastline and can still be with her family that respects her hopes and dreams.

In Riding in Town Cars With Boys, Blair and Chuck are in a life threatening car accident and once they arrive at the hospital, Lily calls Eleanor to tell her. She later mentions that Eleanor, Cyrus, Harold, and Roman are all coming in on the next flight and Eleanor was distraught.

G.G. is Gossip Girl's 100th episode and Blair is preparing to marry Louis. At the pre wedding breakfast, Eleanor is venting about how she feels like she's forgotten something but doesn't know what. Cyrus says he's sure it's all right since one of Eleanor's best and worst qualities is that she never forgets anything. A wedding coordinator approaches Eleanor and Harold, who is also in town, to do the traditional mother-father dance at the wedding. They agree, but Eleanor adds she's in as long as Harold doesn't show her up like he did last time. At the church, Blair and Serena are getting ready when Eleanor and Dorota come in. Eleanor practically cries with happiness at seeing Blair, and says that she knows she once said Blair would never be as pretty as when she's young but she gets prettier everyday, referencing the Pilot episode. Blair has a minor panic attack and Eleanor assures her everything will be fine. After, she reports to Harold and Cyrus that Blair is a nervous wreck. Harold asks what bride isn't on her wedding day, and Eleanor says she wasn't, and has an epiphany. She asks the two men to keep Blair comfortable and calm, and Harold goes to see her but stops and asks if Cyrus is coming to; to which he says Harold is her real father and should go. Meanwhile, Chuck is not planning to attend the wedding and is telling Nate that if he was meant to stop it from happening, there would be some sort of sign when Eleanor walks in. He asks what she's doing there, and she says she was asking herself that the whole way over. She admits to Chuck that when she married Harold, she knew something was wrong because she was so nervous but didn't know what; and that when she married Cyrus, she was very calm and everything felt like it was falling into place. She tells him that Blair shouldn't have to wait for a second time to be happy, she deserves to be happy the first time. Chuck asks what she's saying, and Eleanor says that she finally realized what she as forgetting: Chuck. She goes to leave and asks if he will come to stop the wedding. Eleanor arrives back at the church, and Blair demands to know where she has been since everyone was looking for her. She asks Blair not to be angry with her, and Blair is confused until she sees Chuck, and Eleanor leaves. When Serena and Blair talk later, Eleanor again apologizes for bringing Chuck. Blair says it's okay, she understands why she did it. Harold approaches Cyrus at the church and tells him Blair is having an emergency and needs him. When he reaches Blair, she announces that one father is not enough and asks Cyrus to escort her down the aisle along with Harold and he happily agrees. When Blair walks down the aisle, Eleanor cries. This episode also marks Harold's last appearance in the show.

By the beginning of The Backup Dan, Blair has abandoned her own wedding. Serena approaches Eleanor to ask if she's Blair, and she hasn't. Eleanor asks Serena if Blair seems happy with Louis, and Serena says of course, she's a princess now. Eleanor tells her that all she wants is for Blair to be happy. Meanwhile, Blair is trying to get to the Dominican Republic to get a divorce from Louis without his consent. When the airline attendant is unable to issue Blair a ticket because she doesn't have her passport, she gets the idea to call Dorota to bring it to her. At the same time, Rufus, Lily, Eleanor, and Sophie go to the Van Der Woodsen penthouse after the wedding. Sophie, knowing that Blair left the wedding early, tries to find out her location via Eleanor. She suggests to Eleanor that they call Blair and Louis to invite them over for champagne before they leave on their honeymoon, and since she can't reach Louis, maybe Eleanor can reach Blair. Eleanor declines, saying after the day they'e had, are probably wanting to be alone. Dan calls Rufus and fills him in on Blair's plans, and Rufus agrees to keep things quiet for as long as possible. He tells Blair he told Rufus, who becomes annoyed and assumes Rufus will spill the first chance he gets. Dan argues that she told Dorota, and Blair replies that she pays her to stay loyal. She says Eleanor can't know, since people will be able to tell that she knows, since her face is an emoticon. At the VDW penthouse, Eleanor is unable to reach Blair and assumes her and Louis are already in the air. Sophie asks if Eleanor honestly expects her to believe that. She explains that Louis is downstairs and Blair is missing. Eleanor demands to know where Blair is, and Sophie replies that she will not stand for Louis to face the humiliation of being left on his wedding day. She threatens Eleanor with the dowry payment if Blair doesn't return. Eleanor says that this whole time she thought Blair was with Louis and the dowry was waived because it was antiquated and outrageous. Sophie informs Eleanor that it's in the prenuptial agreement, that if Blair defaults on the marriage, the Waldorf's will be forced to pay it. Eleanor asks how she's supposed to get Blair to return if she doesn't know where she is, to which Sophie doesn't reply. Before she leaves, she tells Eleanor that if she won't tell her where Blair is, there are other ways of finding out. Later, Eleanor sadly tells Lily that she wishes Blair had felt she could turn to her if she was having second thoughts, and that not knowing where she is or if she's okay is the hardest part. Rufus, unable to be quiet anymore, tells them that Blair is fine and with Dan. Rufus apologizes to Eleanor, but that he told Dan he wouldn't say anything. Eleanor tells him there are enormous consequences if Blair doesn't return and demands to talk to her. When she leaves, Lily says Eleanor is probably upset that Blair doesn't trust her like Dan trusts Rufus but that telling her was the right thing to do. Sophie catches up with Blair at a hotel near JFK and informs her that she must return or the Waldorf's will have to pay the dowry. She tells Blair that since the price is so steep, Eleanor will be forced to sell her company. Meanwhile, Eleanor arrives back at the Waldorf penthouse and tells a waiting Louis that she has been looking for Sophie. She says that she knows where Blair is and has no intention of telling any Grimaldi, and that when she finds Blair, she is going to tell her that it doesn't matter what she has to sell because she wants her to stay as far away from Louis as possible. She ends with telling Louis that the Waldorf's do not give into threats and his family can not control hers. At that moment, Blair comes downstairs and tells Eleanor that they can and that she is ready to go on her honeymoon with Louis. Eleanor tells her that she doesn't have to go through with it, and Blair says that she does because she doesn't believe in saving herself and ruining their family at the same time and they hug.

Courtesy of Serena, Gossip Girl is releasing pages from Blair's diaries in The Return of the Ring. In one excerpt, Blair writes about another day of wedding planning where Eleanor makes Blair small so she can be the star. Later, Blair comes downstairs and apologizes in advance to Eleanor if any of her meetings are negatively affected by the revelations in her diary. Eleanor reads aloud a page:

"My mother considers herself an arbiter of Parisian style, but the only French she is intimate with are fries."

Eleanor says that anything Blair wrote has no affect on the business she's in town for, and that she needs to discuss her business with Blair. She agrees to hear Eleanor out once she gets her diary problem fixed. Later in the evening, everyone is planning on attending the Shepherd's divorce party. Serena is determined to not let Blair and Dan be together, and enlists Penelope to keep Blair at the Waldorf's. When Blair is finished getting ready, she runs into Eleanor in her bedroom. She tells Blair she can't believe how much more grown up she is at her age compared to Eleanor, and that it was probably the divorce and all of Blair's mistakes. Blair tells Eleanor that she's stuck between Dan and Chuck. She says Dan is her best friend and she feels strong and safe with him, and with Chuck she's vulnerable but he makes her happy, and she doesn't know which love is better. She admits that Eleanor is probably disappointed since if she was truly powerful, she'd be happy without a man at all. Eleanor replies that even moguls have hearts, and there isn't a woman out there more powerful than Blair and that's why she wants her to take over her company. Eleanor says she has decided to retire, and even though Blair didn't want any part of what she does, she still wants her to run it. Blair excitedly says fashion is art and history and culture and everything she loves combined but she's not a designer. Eleanor says that then her first business decision will be finding the right person to take over. She then asks Blair if a real Waldorf woman will take over Waldorf Designs and she says yes. Penelope shows up and tells Blair that Serena is wearing the same color scheme, and Blair goes into the bathroom. After awhile, Eleanor asks why Penelope is still at the apartment. She says she's waiting for Blair, and Eleanor tells her that she left a long time ago through Serena's room. Once in the car, Blair calls Eleanor and tells her she knows who she needs to be with and she's on her way to tell him now. Later, Eleanor and Blair arrive in Paris and Blair tells her how excited she is to start this new journey.

Season Six Edit

Blair is the new head of Waldorf Designs in Gone Maybe Gone, but Eleanor is not fully convinced that Blair is running things efficiently. Blair insists that if the Olsen twins can run a fashion empire bossing around people, so can she.

In High Infidelity, Blair is meeting with a writer from Women's Wear Daily about her new fashion line. During the summer, Dorota had been left in charge of renovating Waldorf Designs' atelier. She decorated the office with Eleanor's vintage designs, photos of Blair and Serena in the clothes (from Bad News Blair), and a portrait of Eleanor on the wall. Also, Blair has no team of employees since Eleanor's team declined to come back to New York with her. Blair is preparing the office and her samples for the writer when Nelly Yuki shows up. Blair dismisses and berates her before Nelly reveals that she is the WWD reporter. The interview goes horribly and Blair is lost on next steps. She has minions Kati and Jessica sneak a peek at Poppy Lifton's collection, since her clothes will be in the spread next to Blair's, and they report back that she used the same patterns as Blair. She mistakenly assumes Nelly set her up and confronts them at Serena's Conservancy Gala party. The next day, Dorota brings Blair to the atelier where she has found employees from Paris, the Garment District, and Project Runway rejects. Blair gives her new employees a motivational speech, since her only chance of success at Waldorf Designs is her fashion show next week. She asks her employees for a new line in the next ten days, because her old was jeopardized. Dorota laters tells Blair that Eleanor knows she can succeed, and Blair hopes she's right because her entire career and future with Chuck depends on it.

Blair has been working tirelessly on her new collection in Dirty Rotten Scandals to finish it in time for the fashion show. After her original It Girl cancels, she calls Serena to ask her to walk in the show. Serena declines, since they are no longer friends. After the phone call, Blair vents about how Waldorf Designs is the family jewel and she can't let Eleanor down no matter what before passing out. A doctor diagnoses Blair with severe exhaustion and tells her that if she wants to go to the show later, she has to be on bedrest and get IV fluids. While Skyping with her assistant Jean Pierre, Blair is upset at how the setup for the show is going. Chuck arrives and offers to do it himself. Meanwhile, Serena has been chasing Steven's daughter Sage around all day. When she arrives at his place, she finds out Sage told Steven that Serena got her a spot walking in Blair's fashion show. When Steven leaves the room, Serena asks Sage how she got a spot in Blair's show. Sage says she didn't, and blackmails Serena into getting her a spot. When Blair arrives at the show, she is amazed at what Chuck has done. After he leaves, Serena shows up and asks Blair to put Sage in the show. Blair says no, since she needs a real It Girl. However, she eventually agrees to let her in if Serena sits front row wearing vintage Eleanor Waldorf and tells anyone who will listen how beautiful the new collection is and Serena agrees. Blair tells the media that Eleanor will not be attending because she trusts Blair. Once Sage hits the runway, she takes off the dress so she's standing in her underwear. The audience slowly begins to leave after Serena speaks out about how it's embarrassing and the models refuse to walk. Outside, both Serena and Blair realize that Sage pulled the stunt with coercion from either of them. After the show, Jean Pierre calls Blair to tell her that not one buyer has placed an order yet. Nelly also puts a negative review on WWD, mentioning how Blair can't follow in Eleanor's footsteps. Dorota reassures Blair that Eleanor knows she can succeed. Blair panics about how she'll explain to her since she doesn't take kindly to the word failure.

In Portrait of a Lady Alexander, Eleanor knows Blair has no buyers and tries repeatedly calling her. Blair continues to avoid her.

Serena's boyfriend Steven is planning to propose to her in Monstrous Ball. Sage finds out and is desperate to find a way to end their relationship. She makes a deal with Blair that if she wears a Waldorf dress, Blair will stall Serena's proposal. Blair calls Lily and voices her concerns about Serena getting engaged, and Lily takes the bait and doesn't give Steven her blessing. At Cotillion that evening, Sage overhears Georgina blackmail Dan with his sex tape with Serena. She steals her phone and devises a new plan. Once she's being presented, Sage drops the outer layer of her outfit to reveal a revealing dress and Dan and Serena's sex tape begins streaming on the television. Steven sees the tape and breaks up with Serena. When Blair returns home, Dorota tells her she has good and bad news. Eleanor has set a deadline for Blair to have buyers, and Dorota tells Blair that Jean Pierre already has calls from buyers. Blair is excited, since Waldorf Designs will be back in stores before the deadline. Her excitement is short-lived however, Dorota then tells her that Eleanor saw Cotillion photos and is coming home to fix the decorum disaster.

In Where the Vile Things Are, Eleanor returns home and is furious with Blair over Waldorf Designs' being associated with the Serena/Dan sex tape. Blair tells her that the dress was ordered by the three B's: Barney's, Bergdorf's, and Bloomingdale's. Eleanor replies that that doesn't make up for the company losing it's reputation. She blames Blair and her split personality, and says that if she wants to continue running the company, she has to get rid of her devious ways for good. Later, Eleanor admits that Blair has taken some right steps in fixing the problem, but hasn't yet apologized to the masses. She brings out Nelly and tells the girls to talk. Blair makes it through the lunch, and tells Nelly that now she can tell Eleanor that she apologized and they're friends. Nelly refuses and Blair decides to blackmail her with a photo of her in a fat suit in The Age of Innocence (from the season two episode The Age of Dissonance). When Eleanor returns, Nelly tells her that Blair tried to blackmail her and leaves. Blair tries to blame Nelly, but Eleanor says that Dan Humphrey, in his Blair chapter, was right in saying she is running Waldorf Designs like she's still the meanest girl in high school. Blair begs for another chance, but Eleanor demotes her and takes back the presidency. Blair laters calls Nelly and tells her to meet her at Lily's art benefit that evening. At the opening, Blair tells Eleanor she wants to apologize to her and invited Nelly to write about it and restore the reputation. Blair says she's a bad seed, and Eleanor says that no one expects miracles and Blair's scheming has been a part of her for years and it's not going to go away overnight. Blair continues that Eleanor and even Jenny had talent and she doesn't. Eleanor points out her achievements, and Blair confesses that they all stem from scheming, lying, and working the angles because she doesn't have what it takes. She then resigns from Waldorf Designs. Later, Blair tells Eleanor that she was wrong. That her having a dark side wasn't her hiding her lack of talent, her dark side is her talent. She continues by telling Eleanor that in high school, girls wanted to dress like her because they were inspired by her unique ferocity. Eleanor admits that she did instill fear in many, and Blair replies that she needs to stop trying to be like Eleanor and embrace her own individuality. She proposes a line inspired by school uniforms, and Eleanor agrees to give her another chance. They decide the line should be called B.

In the series finale New York, I Love You XOXO, the police are looking for Chuck and Blair after Bart's dead body was found outside the Man of the Year party. When the cops arrive at the Waldorf penthouse, Eleanor tells them that Blair and Chuck's relationship is none of their business. Dorota chimes in that it's too complicated to understand anyway. The cop says that if Blair is with Chuck, she could be in a lot of trouble. Cyrus demands to know what kind of trouble, and the cop says aiding and abetting. Eleanor asks the cop if he really believes Chuck and Blair had anything to do with what happened to Bart, and he asks to check her bed to see if it was slept in. Cyrus says no and no one can ask anymore questions without a lawyer, a lawyer who isn't him and the cop leaves. Eleanor complains that this is outrageous, since it's not like Blair and Chuck killed Bart. Both Cyrus and Dorota say nothing and Eleanor almost passes out. Meanwhile, Chuck finally proposes to Blair and the two get engaged and get married ASAP to get spousal privilege. Everyone including Blair, Chuck, Eleanor, Cyrus, Dorota, Lily, Serena, Dan, Nate, Jack, Georgina, and Sage meet at the Met where they announce their plan to get married. Cyrus and Dorota direct Eleanor to get the wedding dress, Nate and Jack to get the rings, Georgina to get the cake, and Blair and Chuck to stay out of sight. Blair and Chuck successfully get married in front of their family and friends.

In the five year time jump, Blair has moved out of the Waldorf penthouse and into a townhouse with Chuck and their son Henry. Dorota is shown to still be Blair's maid and Eleanor is shown to be absolutely infatuated with her grandson. Cyrus mentions how the place looks great, and Chuck replies that it was all Blair. Meanwhile Blair is shown to be successfully running Waldorf Designs, and she even hired Jenny to create a line called J for Waldorf. The final shot of the Waldorf family shows them to be happy.

Traditions Edit

  • Giant Candy Canes - Every Christmas, Blair and Harold get giant candy canes together to celebrate.In Roman Holiday, Blair ends up giving her candy cane to Roman, as he is an unexpected visitor.
  • Harold's Famous Pumpkin Pie - Every thanksgiving, Harold would serve a delicious pumpkin pie, and Blair would sometimes help him make it. However, in the episode Blair Waldorf Must Pie, Harold doesn't attend thanksgiving as Eleanor uninvited him.

Trivia Edit

  • Harold's nickname for Blair is "Blair Bear".
  • Eleanor and Harold were married for almost 20 years, and remained friendly after their divorce.
  • Harold attended Yale University and brought Blair there when she was little, which sparked her interest in going there.
  • When Lily would jet off with her boyfriends when Serena and Eric were little, they would stay at the Waldorf's and Archibald's, and Eleanor knew that when they showed up with their bags that Lily had a new boyfriend.
  • Eleanor has never met any of Blair's teachers and regularly forgets her birthday.
  • Eleanor was in labor with Blair for 23 hours.
  • Blair and Eleanor adore Cyndi Lauper and used to act out "Girls Just Wanna Have Fun". Their first DVD was Vibes.
  • Blair slept in Harold's Yale University sweatshirt until it fell apart.
  • Harold was invited to the dean of admissions private dinner party when he applied to Yale, and Blair also attends but because she schemed her way it.
  • Blair and Serena first went to Yale when they were nine for the Harvard - Yale game, brought by Harold, and Blair tacked Senator Chuck Schumer's daughter for wearing a Harvard sweatshirt.
  • Blair and Serena played in Eleanor's vintage Manolo's when they were eight.
  • Eleanor's new husband Cyrus was one of her attorneys when she and Harold divorced.
  • In You've Got Yale!, Harold and Roman bring Blair a bulldog, although he is never seen in the series again after Harold goes back to France.
  • Cyrus' mother hates Eleanor.
  • Both Harold and Eleanor eventually move to France leaving Blair the only Waldorf in New York. 
  • Dorota believes that Harold and Eleanor's marriage didn't work out since they had no tradition at their wedding.
  • Eleanor and Cyrus are Dorota and Vanya's daughter Anastasia's godparents.
  • Blair has two dads (Harold and Cyrus) who are lawyers.
  • At Harold and Eleanor's wedding, the quartet had to stall for twenty minutes until her Xanax kicked in.
  • Eleanor refuses to get Botox.
  • Harold is the only member of the Waldorf family not to attend Blair and Chuck or Serena and Dan's wedding.

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