She goes to the VDW's and succeeds in getting him to kiss her, but their foreplay is interrupted when a text from Serena reveals her plans. In a last ditch attempt, Blair decides to just tell him how she feels at Rufus Humphrey 's art gallery opening. Before she goes through with it, Dan finds out what she and Chuck did to Vanessa so he instills doubt in her telling him. As a result, she fails in doing so and Chuck, annoyed with her games, ends their relationship for good. However, Dan tells Chuck that he ruined Blair's revelation and was the result of the failure.
Later that night, Chuck goes to see Blair and tells her that despite their mutual attraction to each other, they aren't ready for a relationship. They agree that they love the game too much to stop, and they decide to put their relationship on hold Pret-a-Poor-J. While babysitting a prominent Yale donor's daughter named Emma, Blair and Chuck end up on a wild goose chase to find her after she runs away, determined to lose her virginity.
They eventually find her at a hotel with a boy from her school nicknamed "The Devirginator", but Chuck has Gossip Girl send out a fake blast about Emma's enemy Muffy losing hers first.
Disappointed, she goes home with Blair, who recognizes parts of herself in Emma. She asks Blair if she lost her virginity to someone she loves, and Blair says yes. Soon after, Blair is officially rejected from her dream school, Yale University, so she goes in search of a wilder lifestyle: which includes Chuck's enemy, Carter Baizen. During a party thrown by Nate's family, Chuck and Serena attempt to find Blair to change her back to who she was before.
When Chuck finally corners her, she refuses to change back to who she was and tries to proposition him into having sex with her. He refuses, claiming it isn't the Blair he wants, so she leaves him. Later that day, Nate sits down with her and they have a deep talk about not fighting against who you are. That night, Chuck goes to the Waldorf's to talk to her, but finds Nate's jacket and realizes he's upstairs with Blair The Grandfather. They become closer again, which makes Chuck jealous.
He tries to tell Blair that she never had any sparks with Nate, and reminds her that there's a reason he won't break up with Vanessa. Trying to prove Chuck wrong, she attempts to get Nate to break up with Vanessa to be with her; which he eventually does. However, a still jealous Chuck finds Vanessa after the break up and tells her that Nate left her for Blair.see
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Angry, they try to come up with a way to get back at them. After seeing them together at Jenny's Sweet Sixteen party, they kiss. Both Blair and Nate see, but it doesn't bother them too much as they get back together officially the next day while Chuck has sex with Vanessa Remains of the J.
However, Blair is suspicious of him and becomes even more so when Serena tells her that Gabriel has a tendency to disappear at times, isn't easy to make plans with, and that he supposedly met Serena while she was impaired with Georgina at a restaurant Blair closed down herself to use for a scheme. On one occasion, she waits outside Serena's building to see where he'll disappear to and Chuck sees her spying together. They see him meet up and kiss Poppy, and together they decide to expose him.
When Nate finds out they were together, he buys an apartment to live in with Blair while they go to different schools. He also tells Chuck to stay away from Blair unless he's going to tell her how he feels because he wants her for himself. When Nate finds out Chuck wants Blair to go with him to talk to Georgina, he asks Blair to stay with them in their new apartment but she chooses to go with Chuck.
However, after the two fall asleep together all night in his limo waiting for visiting hours, she realizes he only brought her to keep her away from Nate. On his way back into the city, Chuck learns that Serena has found out that Gabriel is indeed lying to her about meeting her and she doesn't know what else he's lying about. Together with Blair and Nate, they corner Gabriel into confessing that Poppy is pulling all the strings and is taking money from their faux fundraiser for herself.
They set up Georgina to meet with Poppy to catch her in the middle of conning but and while this is being carried out, Blair asks Chuck if what they have is real or if he's just playing a game with her. Fearful of not being able to make her happy, Chuck lies that he's just messing with her and Blair leaves crying The Wrath of Con. The next day, Nate finds out that he is unable to get a limo for prom, that he can't get a corsage, his hotel plans were ruined, and Blair's dress was destroyed at the dry cleaners. He asks Chuck if he had anything to do with the sabotage, but he denies it.
Meanwhile, Blair receives her dream dress from Paris to wear, and Chuck gives Serena the key to the penthouse at The Plaza Hotel to give to Blair: both things Blair planned out in her prom scrapbook as a child. At prom, Penelope, Hazel, Isabel, and Nelly plot to humiliate Blair by rigging the prom queen election to make Nelly win but are shocked when Blair is announced the winner. Privately, Chuck reveals that he voted for Blair about times and removed all the ballots for Nelly from the box so she could have the prom of her dreams. At the end of the night, Blair and Nate break up due to feeling like they've outgrown their relationship Valley Girls.
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At Nate's graduation party that night, they end up in a room alone together and are about to admit their feelings when a Gossip Girl blast reveals that Chuck slept with Vanessa and Blair slept with Jack on New Year's. As a result, Chuck loses any interest in being with Blair, even though she tells him she loves him. A week later, Blair tells Serena that she is planning to have a quiet summer and she knows that Chuck has been in Europe.
Later that day, Blair is walking home when she sees Chuck waiting for her on the street. He explains that while he was in Europe he couldn't get her out of his head and brought her her favorite things to make things right. Finally, he admits that he loves her too and they kiss; entering into a relationship. Soon after, he becomes immersed in his work and Blair continues to struggled at NYU. After she decides to skip a movie premiere her whole dorm was invited to, he invites Jenny to go with him in her place.
When she finds out, she tracks them down and begins to lay into Jenny until Chuck admits it was all his plan. He tells her that she is special and will achieve what she wants in due time. After they talk, she is stopped by a paparazzo who asks to take her photo. It's later revealed Chuck paid the photographer to take the photos as a way to help Blair feel special and give her some confidence Dan de Fleurette.
In Inglourious Bassterds , Jack tells Chuck if he wants the hotel back he can have it: in exchange for a night with Blair. Later, Jack runs into Blair and says that his price for the hotel is a night with her but Chuck never considered it. However, after Jack sends her a dress saying she has one last chance to save Chuck and seeing how crushed Chuck is from losing his hotel, she goes to Jack willingly; but brings a contract to sign to make sure Chuck never finds out and that he holds up his end of the deal. Instead of doing anything with her, he tells her how everything was set up by Chuck because he knowingly sold her out for his hotel by preying on her compassion and need to help.
She goes home to find Chuck in the lobby of her building and they fight over what just happened. He tells her that even if he set her up, no one forced her to go see Jack and she slaps him before going upstairs alone. In the season premiere Belles de Jour , Blair and Serena are wrapping up their summer in Paris together. Blair mentions Chuck has been off the grid since they left New York and she just wants to have one nice date before they go home. Soon after, she meets Louis Grimaldi , a prince from Monaco.
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She goes on a double date with him, Serena, and his friend Jean Michele. However, the date ends after Blair learns Serena will also be attending Columbia University in the fall and Louis reveals he thinks Blair is only after his title. Afterwards, Blair confides in Serena that she's worried that she will never be able to move on from Chuck.
Meanwhile, Chuck is on his way to Paris with a woman, Eva Coupeau , who saved his life after the shooting, and is pretending to be named Henry Prince. Afterwards, Blair begins to build a real friendship with Dan, which leads up to them sharing a kiss to find out if they have feelings for each other Empire of the Son. After Raina begins dating Nate, Chuck realizes he really does want to be with Blair, but finds out she kissed Dan. When he confronts her, she admits that while it was life changing, it only was because it made her realize she wanted to be with him. She also tells him that even though she knows she's ready for them to be together and build a future, she knows he isn't ready yet; putting their relationship on hold once again The Kids Stay in the Picture.
Right after, Louis comes to Manhattan looking for Blair. They plan to attend a ball together to earn Louis' mother Sophie Grimaldi 's approval so they can get engaged, but Chuck crashes it to win Blair back. He's escorted out, and Blair leaves due to being humiliated. However, Louis follows her home and proposes to her. She immediately accepts, and goes to The Empire to tell Chuck. When he finds out, he goes into a rage; which includes him punching a window in his penthouse, causing glass to go flying and one shard cuts Blair's cheek. Terrified, she runs out on him The Princesses and the Frog.
Meanwhile, Sophie is suspicious of Blair and tells Louis that the first thing she did after getting engaged was go see Chuck. After finding this out, Louis decides to follow Blair and sees her with Chuck, warning him that Jack is back in town. At an engagement party thrown by Eleanor and Cyrus , Louis tells Blair to either meet him at Constance Billard 's annual alumni gala prepared to share every part of herself, or not come and end it with him Shattered Bass. Before she can go to Constance in the finale The Wrong Goodbye , Blair is lured to Chuck's new hotel site by Russell; to be burned alive in the building the same way his late wife was.
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However, Blair is able to reach Chuck via her speed dial and he arrives, along with Nate and Raina, to save her. When they're out of the building, they sneak into a bar mitzvah to have a drink and relax before she goes to see Louis. While at the party, they end up having sex and Blair tells Chuck that even though she's happy and secure with Louis, they don't have the passion that she has with him. After hearing this, he stops Blair from ending things with Louis and gives his blessing for them to be married. They admit that they will always love each other and say goodbye.
The last shot of the episode shows a positive pregnancy test in Blair and Serena's shared bathroom. Soon after, Chuck begins to see a therapist and is finally able to let Blair go by returning the engagement ring he bought her The Fasting and the Furious. However, it's revealed that Dr.
Barnes, his therapist, was being paid by Louis to ensure Chuck act out in a way to drive Blair away forever. In Rhodes to Perdition Chuck informs Blair that he returned the ring and she realizes that maybe Louis isn't the right choice anymore. Blair plans to leave Louis and Chuck prepares to welcome her and her unborn baby with open arms. However, Serena's cousin Charlie Rhodes Ivy Dickens is still paranoid about being found as a fraud so she calls paparazzi to storm her debut party as soon as Chuck and Blair leave together. They're followed by the photographers and end up in a horrible car crash.
As a result, Chuck does live but Blair distances herself to make sure he stays safe. However, Chuck can't understand why Blair can't talk to him and resorts to stalking her to figure out why Father and the Bride.
Before the ceremony, Blair confesses her love to Chuck but unbeknownst to the both of them, Georgina films the entire thing and lets it play during the vows.