Chuck and Blair are 100% the best relationship to be in Gossip Girl. The relationship can be so unhealthy at times but is so consumed by love and passion, you forget how truly twisted the whole situation is and soon enough you're asking yourself "where's my Chuck Bass?"
Chuck and Blair have never been the simple and normal type of couple, they like to be kept on their toes, they like to play games because it keeps things in their relationship exciting. In Season 1 of Gossip Girl, Blair is of course, dedicated to the popular and most pretty boy, Nate Archibald. It is clear to see at the beginning that Blair doesn't care for Chuck at all, however, you would always see them scheming together to keep their power at the very top. They both like to have people worshipping the ground they walk on and that's what they always did, even if it meant blackmailing and manipulating people. Neither Chuck or Blair had any kind of feelings for each other whatsoever.
The first glimpse of Chuck and Blair's romance blossoming is in the episode 'Victor, Victrola' where Blair has just broke up with Nate and needs to let loose. She finds herself at Chuck's Burlesque club, where she puts on a strip teasing show. Chuck watches her, so enticed by her movements and he hasn't looked at her this way before. This is where the famous limo scene comes up, Chuck takes Blair home in his limo and things begin to get steamy. Blair is the one, surprisingly to make the first move, leaning into kiss Chuck. This is where Blair gives her virginity to Chuck.
After losing her virginity, Blair is dedicated to getting Nate back as she knows where he heart truly lies. Chuck on the other hand, begins to grow feelings, he states that he has a fluttering feeling in his stomach, where Blair simply says "the butterflies have to be murdered". Chuck grows more and more feelings for Blair as the episodes go on and even tries to convince Nate to break up with her by creating lies and letting his jealousy take over. After taking his jealousy to the extreme by being the reason Nate punches Carter at the ball. Blair ends her and Chucks relationship once and for all, leaving him heartbroken.
Chuck finally cracks in 'A thin line between Chuck and Nate' and tips Gossip Girl with the news about him taking Blair's virginity. Nate and Chuck's friendship comes to an end and Chuck tells Blair he wants absolutely nothing to do with her. Their mutual relationship finishes there until they are brought back together to help Serena. Chuck and Blair reconcile at the Bass-Van Der Woodsen wedding where Chuck's best man speech is inspired by Blair. Their romance begins to spark back up until he leaves her at the heliport, where he told her they would fly to Tuscany together.
At the beginning of Season 2, we learn Chuck has been trying to get over Blair by sleeping with many girls in the Hamptons. Blair had gone to Europe and grabbed herself a new man, Marcus. Chuck reveals to Blair that he was afraid if they spent the whole summer together, she would see the real him and not want him any more. Blair responded that she will be his and only his, if he tells her he loves her. Chuck can not expose himself in that way, leaving Blair no choice but to stick it out with Marcus and try to move on. After troubles with Marcus, Blair goes back to Chuck who demands she tells him she loves him, or she won't get what she wants. She refuses to expose herself as well, leaving Chuck no choice but to give up and let Blair do the chasing for once. Chuck visits Blair after going through her games and manipulations, explaining the reason they won't say "I love you" is because that means they'll be closer to one another and he admits he's not ready for anything close to commitment. Chuck and Blair put their relationship on hold. Throughout the rest of season 2, their relationship is on and off. They try to find each other dates for events but end up coming together, Blair finally says that she loves Chuck when he is having a major breakdown over his dad's death, he shrugs her words off but finds his way back to her later on where he stays the night, Blair wakes up to a note revealing Chuck has fled the country and she shouldn't try to find him. Chuck eventually returns with his uncle, Jack Bass and shuns Blair's affection. After catching Chuck on the edge of a building, Blair talks him down from the ledge by saying she would care if he died and she needs him, Chuck eventually gets down after Blair's speech, falling into her arms. Chuck is given the job to become CEO of Bass industries but turns it down knowing how stupid the idea is because his father always thought of him as a failure. Nate and Blair convince Chuck to take the job but his Uncle Jack has other plans to get him caught by the board members, drunk, with prostitutes and drugs. Chuck tries to apologise to Blair about his actions, after seeing how proud Blair was of him but she never forgives him. Blair gets herself into a rebellious stage and starts dating Carter Baizen who only brings out the worst in her. Blair tries to seduce Chuck at a party but he refuses her offer as she isn't the Blair he wants right now. Blair starts her relationship back up with Blair and Chuck ends up having a 'thing' with Vanessa. Once again, Chuck and Blair come together for a scheme to help their friend Serena get out of her troubles. Blair needs to hear how Chuck feels before she can really start things up with Nate again where he only responds with, "it was just a game". Serena questions his choice of letting Blair go and Chuck tells Serena he loves Blair, but he wants her to be happy and he believes he can't make her happy. At the prom, Blair wins prom Queen with the help of Chuck voting for over 100 times, after seeing Nelly trying to sabotage the voting ballots. Blair breaks up with Nate again, seeing he is only her high school boyfriend. In the last episode of Season 2, Chuck and Blair almost get back together until he finds out Blair slept with his Uncle Jack, last New Year's Eve and she finds out he slept with Vanessa. Weeks later, he comes back from Europe and finally tell's Blair he loves her.
The start of Season 3 shows Chuck and Blair in a happy and playful relationship. The pair have created a game where they choose potential girls to victimize, Chuck seduces them and just as they're about to kiss Blair catches them. Blair worries that without games, they'll just be another boring couple. Chuck reassures her by saying they could never be boring and he wouldn't be Chuck Bass without her. They then start role-playing.
Throughout Season 3, Blair starts her new college life and Chuck is the new founded owner of the famous Empire Hotel. A place all Gossip Girls fans would love to stay. Chuck is so busy with his new purchase, he hasn't had enough time with Blair and hasn't seen how insecure she's feeling with not being accepted by the other students at NYU. He also founds out she's been getting herself back into the Queen B drama at Constance, so he makes it a mission with the help of Jenny to get Blair to come back down to reality and Jenny can go back to being the Queen of Constance. Again they have their manipulating games on one another, spiralling them downwards and losing their trust for each other. Blair tries to keep Chuck calm as it approaches the first anniversary of his father's death and he has to reminisce on the whole thing when Serena ends up in hospital. Chuck has hallucinations of his dad telling him how weak he is for giving Blair his heart, this makes him distance himself away from Blair. Blair eventually convinces him to visit his father's grave where he bumps into someone that is possibly his mother. However after many days of bonding and betrayal, she reveals to Chuck that she is not his mother. After Elizabeth and Jack managed to get Chuck to hand over his hotel, Jack offers him his hotel back under one condition, a night with Blair. Jack tells Blair that Chuck can have his hotel back if she spends one night with him, Blair sees that Chuck is crushed so she has no other choice but to go through with the night. Jack reveals to Blair that Chuck and him had it planned all along and Chuck wanted Blair to feel compassion and run to Jack. Blair is completely devastated and broken hearing that Chuck traded her for the hotel. Although Blair said she would stand by him on the worst thing he could ever do, she didn't know the worst thing he could ever do would be to her. Blair slaps Chuck in the face and leaves him after telling him "Goodbye, Chuck".
Chuck does everything in his power to get Blair back, including throwing a traditional wedding for Dorota and Vanya. Dorota asks Chuck and Blair to be the happy couple to escort them for good luck and Blair accepts because she's so embarrassed and doesn't want anyone to know about the trade. However she does tell Nate and he gets into a fight with Chuck. Blair can't deal with faking her happiness and breaks down telling Dorota that Chuck and her aren't happy. Chuck begs Blair to not give and to see this through to the end, Blair finalizes everything by saying "this is the end". Chuck goes back to his ways of seducing any woman he comes across to get over how devastated he truly is.
A scheme eventually brings them back together and Chuck tells her that saying he loved her was the most dangerous thing he's ever done. He tells her that the next day, he will be standing at the top of the Empire State building, if she doesn't arrive by 7:01, he will close his heart to her forever. Blair tries to keep herself as far away from the Empire State building as possible but after seeing so many signals telling her to go, she decides to meet him. Dorota's water breaks at the very same time, leaving Blair to leave her choice to see Chuck behind for the time being. By the time she makes it to the Empire State building, Chuck has left and she finds peonies in the trash. Chuck goes back to the hotel, thinking Blair doesn't love him any more and ends up sleeping with Jenny to take away the pain of being rejected. Blair arrives at the hotel with the peonies in her hands and tells Chuck she was late because Dorota had her baby, she tells him she followed her heart because she loves him and they hug but Chuck still has the Jenny situation to deal with. Chuck apologises to Blair about everything and he wants to spend the rest of his life making it up to her, he's just about to propose when Dan comes through the lobby and punches Chuck in the face. At that moment, Blair realises Chuck had slept with Jenny and she banishes Jenny from New York permanently. Blaire and Chuck are left alone, allowing Chuck to apologise once again but Blaire tells him to never say anything to her ever again and leaves. Chuck ends up in Prague drunk and upset, he is assaulted by thieves when they try to steal the engagement ring from him, he fights for the ring but ends up getting shot in the middle of it.
In Season 4, Blair makes it her mission to get back to dating when Gossip Girl announces that she had a summer without any sort of romance. Blair notices that Gossip Girl hasn't posted about Chuck all summer and she ends up cracking, telling Serena that she's tried to fake being okay throughout the whole of the summer but in reality, she's not okay and she is worried she'll never be able to move on from him. Chuck is shown with a new woman named Eva who nursed him back to health after finding him shot. Chuck decides to live with a new identity (Henrey Prince) and stays in Paris. Blair and Chuck do cross paths through traffic but she insists the driver to keep moving. Blair starts up a new romance with a prince, Louis. Serena goes to see Chuck and tries to convince him to not give up his old life, he will lose everything if he does. Chuck tells Serena he's already lost everything (Blair) and Serena knows the only person who can stop him from leaving is Blair, Serena goes to convince Blair to save Chuck. Blair is reluctant to help at first as she has her priorities with Louis. Blair stops by Harry Winston and a ring catches her eye and she is informed that it has already been purchased by a 'Mr Chuck Bass'. Blair is taken aback after realising Chuck was going to propose to her but it somehow convinces her to go and see him. She finds him at the Paris train station and tells him changing his name won't change everything he is, he tells her he wants to become a better man after destroying the only thing he ever loved and that her world would be better without him. Blair tells him, although she doesn't love him anymore, it wouldn't be her world if he wasn't in it. Chuck is convinced and reveals his true identity to Eva and invites her to join him in Manhattan. Blair hates how happy Eva is making Chuck and does everything to find a way to break them apart. She sees Eva selling a Cartier watch that Chuck bought her, only to find out she was helping a man who was about to lose his home. Blair decides to dig deeper into Eva's past where she finds out that Eva was a prostitute. Chuck confronts Eva before Blair can say anything about it and Chuck forgives her just like Eva forgave him for his past. On the night where Chuck announces which charity he will be donating too, Blair sees that her attempt of breaking them over the prostitution scandal has failed and turns to stealing Chuck's passport and placing it into Eva's luggage so it looks like Eva knew who Chuck was from the first day he met her. Chuck ends up devastated once again and tells Eva to get out, however, Chuck soon finds out this was all a set up but by the time he goes to find Eva and apologise, it's too late and she's already decided herself that she wants to leave. Blair still denies her feelings towards Chuck, so he only assumes that she just wants to ruin his chances of happiness out of hatred, Blair also denies that but Chuck has had enough and declares war. Chuck is determined to take everything away from Blair including bringing Jenny Humphrey back to Manhattan where Jenny tips Gossip Girl to tell everyone about her sleeping with Chuck, leaving Blair ashamed and embarrassed, before Jenny leaves she confronts the two of them by saying "you two used to be so in love, and together you were invincible, but now that you've turned against each other it's only a matter of time until your mutual destruction". Chuck and Blair agree to a truce which is made official by Nate and Serena who make them agree to a peace treaty. Dan and Eric do everything to make Chuck and Blair break their peace treaty but they only brush them off knowing they have so many enemies. However, after a few slip ups at her 20th birthday party, Chuck and Blair agree that the peace treaty just won't work because they hate each other too much, Chuck rips up the treaty then grabs Blair and they start kissing and it ends with passionate piano sex.
Chuck and Blair begin sneaking around to have a lot of sex but soon they realise they'll never be able to get over each other if they keep playing these games while they have so much history. Blair believes she should go on a cleanse to stop herself being pulled back in, Chuck believes they need immersion therapy (so much sex that they get sick of each other). Blair is almost convinced but she has to go back to scheming, after their successful take down Chuck and Blair share celebratory champagne and agree to be just friends. As Chuck leaves, they share a kiss and Chuck ends up carrying her to her room.
Chuck and Blair are both told that their relationship would be disastrous for their future careers so they decide to keep their 'friends with benefits' relationship a secret. In the heat of the moment, Chuck tells Blair he loves her and she avoids it, eventually it eats away at her and she confronts him about it at the saints and sinners party. He tells her he meant it with all his heart and she tells him she loves him too. While in a passionate kiss, they are revealed infront of everyone, leaving Blair to lose her chances at being the face of Anne Archibald's foundation. She chooses to be Blair Waldorf before becoming Chuck Bass's girlfriend. Chuck is understanding about this and answers back with "if two people are meant to be together, eventually they'll find their way back"
They remain friends and on the odd occasion ask each other for help.
Chuck begins to fall for a girl called Raina Thorpe and Serena protects Blair by not getting her to do a story on Raina because she'll end up getting herself hurt. The Chuck and Raina romance doesn't last long as she walks away after hearing what he did to Lily. Chuck tries to rekindle his relationship with Blair but hears she had a life changing kiss with Dan Humphrey. She tells him it was life changing, but only because it made her realise that she wants to be with Chuck. Blair tells him that she knows she's ready for their relationship to start back up but she also knows that Chuck isn't, once again she tells him sorry and walks away.
Prince Louis makes an appearance in Blair's life as they begin dating and things move pretty fast between them. Chuck is convinced Louis is a distraction and he is Blair's soul mate. Louis proposes to Blair, Blair accepts, excited to finally get her fairytale. Blair tells Chuck about the engagement before anyone else can and Chuck loses himself completely and grabs Blair telling her "you're mine" and punches the window, cutting her face in the process.
Chuck gets himself back into trouble with Raina Thorpe and her father and as revenge for turning his daughter against him, Russell lures Blair to Chuck's hotel because he knows Blair is the one he loves more than anything. Russell threatens to light the building on fire and leave Blair in there to burn. Chuck saves Blair just in time, luckily Blair had him on speed dial. Chuck takes Blair to a Bar Mitzvah to calm her down and they have a lot of fun together. Blair realises she still has feelings for Chuck, instead of going back to Louis, they sneak off to the back room to have sex.
Blair decides to break things off with Louis, she knows Louis is better for her but Chuck is her 'epic love' and they will always be drawn back to each other. Chuck, however, believes he should let Blair go because he is sure her love with Louis is the 'right love'. Chuck gives Louis his blessing and they say their last "I love you's" before walking away from each other.
In Season 5, Chuck hires men to beat him up as he feels numb after Blair leaving him for Prince Louis and hopes pain will make him feel again. Blair finds out that she's pregnant and isn't sure on if Chuck or Louis is the father. She takes a pregnancy test revealing that Louis is the baby's father. Blair tells Chuck the news of her being pregnant and that it is Louis' baby, she tells him a part of her hoped it was Chuck's. After hearing the devastating news, he begins to feel again.
Chuck begins to see a therapist and goes to Blair's apartment to apologise for everything he did wrong in the past years and he's assured her that he'll take care of himself from now on. Chuck returns the engagement ring to Harry Winston and finally let's Blair go.
Blair isn't convinced that Chuck has changed for the best and wants to prove that he still is the evil person he always has been so she can know for sure she's made the right choice to be with Louis. Chuck does crack eventually and kisses her back, earning a slap across the face for not changing that much. Little did Blair know, he kissed her on purpose so she could finally move on herself, thinking Chuck is still the same selfish person he always has been. Blair starts falling for Chuck again after spending the day with him and tries to get him back. Chuck makes it clear that she shouldn't break up her family and she decides to finally marry Louis. Dan see's how hurt she is, he reunites them in a candlelit room to let them work things out. Chuck and Blair flee town but the car was intended for Nate and has some mechanical problems. Chuck is excited about Blair's decision and Blair assures him he's the only she's ever wanted. The driver loses control because of paparazzi surrounding the car they wind up in a major car crash. Blair becomes conscious but Chuck remains fighting for his life. Chuck loses a lot of blood and Blair loses her baby. Blair makes a pact to God to marry Louis because she's worried something else will happen to Chuck if she's with him. Blair still struggles saying she feels dead inside without him.
Blair's wedding day finally arrives. Chuck comes to see Blair and he asks her not to marry Louis. Blair tells Chuck he loves her but they can't be together. Midway through the wedding, the video showing Blair telling Chuck she loves him is revealed. Blair apologises to Louis and the wedding carries on. At the reception Louis reveals that he no longer loves Blair and their marriage is all for show. Blair leaves her reception and heads to the airport so she can flee to the Dominican Republican for a divorce. She doesn't make it because she has no passport so hides away in a hotel. Chuck finds her and tells her he will protect her from whatever Louis' family is going to throw at her. Blair decides to go with the year plan of being married or she has to pay the dowry which will leave her family bankrupt.
Chuck secretly pays her dowry so she can have the freedom she deserves and she starts dating Dan. Blair finds out about him paying the dowry and thinks he's just trying to buy her back. Chuck only wanted her to be free and to be with whoever she loves. Chuck and Blair start scheming together again, Blair has to deal with an insecure Dan and they both find out Chuck's dad is still alive.
Blair accepts to accompany Dan in Rome but doesn't seem too thrilled about it. Instead of being at the meeting for Rome with Dan, Blair chooses to help Chuck, leaving Serena to take her place and pretend to be her. At the end of Season 5, Blair chooses Chuck but Chuck has lost his place in Bass Industries since his dad's return and he rejects Blair. In Monte Carlo, Blair tells Chuck that it's her turn to fight for him and she's all in.
In Season 6, Chuck and Blair promise each other they'll be together after they've took care of their own issues. Blair, running her mother's company and Chuck, taking down his father. Blair wears her engagement ring on a necklace around her neck. Blair's career only becomes bigger and better while Chuck is having no luck with destroying his father. Chuck almost gives up telling Blair her ring will never be round her finger. After a lot of scheming about, Chuck faces his father and his father plunges to his death in an attempt to attack Chuck who dodges him, letting Bart go over the building. Chuck and Blair run away after realising police are after Chuck for being a possible witness. The only witness beside Chuck was Blair who will also be questioned and be put into a lot of trouble. Chuck's uncle Jack suggests the only way to protect Blair from having to say anything is for them to get married. Chuck finally proposes to Blair and she finally accepts. Chuck and Blair call their family and friends and they finally get married at Central Park. Police have been tipped about their whereabouts so the wedding has to be rushed and after they've kissed, they get taken away but get released straight away because police have no evidence.
In a five year jump we see that Chuck and Blair are still happily married with a son called Henry.
OMG I AM SO SORRY THIS IS SO UNBELIEVABLY LONG I JUST NEEDED TO TYPE OUT THEIR WHOLE STORY OTHERWISE YOU WOULDN'T UNDERSTAND WHY I AM SO OBSESSED WITH THEM!!
- Shelby xxx
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