These 40 Chuck & Blair Moments Will Have You Feeling So Nostalgic

Since the show’s premiere in 2007, Chuck and Blair from the CW’s Gossip Girl have become one of television’s “it” couples. The original Gossip Girl is revered among Gen Z, and for good reason: The drama, friendships, scandals, and love triangles all combine with their iconic fashion statements to make the show a timeless young adult classic, even after it ended a decade ago.

Chuck and Blair are one of the show’s most prominent couples, both being calculated, scheming, and confident throughout the show’s run. Their relationship came as no less than a surprise in the first season, but as the series progressed, fans rooted for and definitely swooned over their romance (even with the constant breakups and reunions). 

Just spotted: 40 Chuck and Blair moments that should never be forgotten. XOXO, Her Campus.

Season 1, Episode 7: Chuck and Blair’s first night together

Who could forget how Chuck and Blair first ended up together? Blair decides to push her feelings aside after her official breakup with her childhood sweetheart and teen heartthrob, Nate Archibald, by partying at club Virtola (which is ironically owned by Chuck). Chuck decides to drive Blair home in his limo, which quickly escalates into the two having a full-on hookup sesh.

Season 1, Episode 8: When Chuck proved just how romantic he can be

Blair is sad and alone on her birthday. She broke up with Nate again after discovering that his intention to get back together was a scheme devised by their parents. Chuck pays Blair a visit and brings her a gift: the diamond necklace she expected Nate to give her. Turns out Chuck was the one who placed it on hold at the jeweler, not Nate. He assists her in putting it on and remarks that “something that beautiful should be on someone worthy of its beauty.” Brb, making that my next Instagram caption. 

Season 1, Episode 18: When they still were in the early stages of flirting

Blair wakes up to find Chuck on her bed after staying up most of the night devising a plan to exact revenge on Georgina. When she questions him about it, the two start bickering and flirting with each other, until Blair slams the door in his face. Aw, young love!

Season 1, Episode 18: The kiss that signaled the start of a blooming romance 

In the Season 1 finale, Chuck asks Blair to save a dance for him after his best man’s speech for Bart and Lily’s wedding, which Blair declines. They ended up dancing together anyways after Chuck delivers his moving speech, which was influenced by Blair in the audience. The interaction was sweet, and it led to them sharing a kiss, kicking off their new fling!

Season 2, Episode 1: “Three Words, Eight Letters”

Blair returns to the U.S. after spending the majority of the summer in Europe and joins the gang for their summer trip to the Hamptons. Chuck approaches Blair one last time after attempting to win her back since abandoning her on the tarmac and admits he should never have left her. He demands that she not leave with Marcus, an English lord who is now Blair’s new boyfriend, and she pleads that he provide her with a reason not to go. Blair eventually tells him one of the most iconic lines in Gossip Girl history: “Three words, eight letters, say it and I’m yours.” The line was an attempt for Chuck to finally tell her he loves her, but he is unable to do so.

Season 2, Episode 3: The switch-a-roo makeout session

After Chuck fails to admit that he loves her, Blair begins to officially date Marcus. The only issue with their relationship is that Blair wants to take it to the next level, but Marcus is hesitant and frequently redirects the conversation. In Episode 3, Blair becomes impatient and begins to ask Marcus to meet her in the bedroom, but Chuck overhears and follows her. Chuck begins to impersonate Marcus and adopt a British accent (which is ironic given that Ed Westwick, the actor who plays Chuck, is English in real life), leading the two to make out after the candles burn out. We find out Blair knew it was Chuck the entire time; talk about a total plot twist.

Season 2, Episode 13: Blair confessed that she loved Chuck

Chuck is left in emotional ruins after the death of his father, Bart, and has cut himself off from his family and the rest of the group. Before Blair can stop Chuck from leaving the city, she begs him to stay and tells him for the first time that she will be there for him through anything because she loves him. Chuck dismisses her confession with a cold “that’s too bad” before entering his limo and driving away.

Season 2: Episode 13: When Chuck came to Blair for comfort

In the same episode, Blair receives a message from her maid Dorota, prompting her to rush upstairs to find Chuck in tears sitting on her bed. She ended up quietly embracing him for the duration of the scene. Later, the two lay in bed together, as she frequently checks on Chuck while he sleeps. Blair eventually falls asleep and wakes up to find Chuck gone. He left a message apologizing for everything and requesting that she find someone better that she deserves, and not come looking for him.

Season 2, Episode 14: When Blair saved Chuck from falling from the roof

Chuck is found by his uncle in Bangkok after attempting to flee his problems and is returned to his home in Manhattan. Chuck’s erratic behavior frightens the group, which is heightened when he tells Eric he’s going to the roof and that it was nice having him as a little brother. Blair follows him to the rooftop and says she does and always will want him and that she couldn’t bear it if anything happened to him. She reaches out her hand and pulls him back from the edge. He collapses into her arms once he’s down, and she embraces him. 

Season 2, Episode 19: Chuck’s concerned for Blair’s wellbeing

While the two were not on the best of terms, Chuck continued to show Blair compassion when both he and Serena became concerned about her new carefree behavior. Chuck used Serena’s phone to check for a response, and while Serena assumed it was Blair’s lack of interest in Chuck’s advances, Chuck pointed out that she had been out all night. Blair, now intoxicated, begins to make a scene, prompting Chuck to arrive to assess the situation and protect her. He leads her into another room and informs her that destroying the old her will not make her happy. She kisses him, reminding him of their first night together, but he stops her and says she’s not the Blair he’s looking for.

Season 2, Episode 20: Tried to make Blair jealous

After discovering Nate and Blair’s growing attraction, Chuck sets out to separate the two, beginning by informing Vanessa that Nate was cheating on her. Chuck and Vanessa attend the party together, and when they arrive, Nate and Blair are already together. Vanessa and Chuck kiss in front of the two in order to make them jealous.

Season 2, Episode 23: Chuck admited to Serena that he loves Blair

While Blair and Chuck are sitting at the bar, Blair asks Chuck if his feelings for her are genuine or if he sees it as a game. He responds that it’s just a game and that she is free to leave at any time. As Blair walks away, Serena asks Chuck why he would do such a thing, to which he responds, “Because I love her and I can’t make her happy.” This is a bittersweet confession because we finally get to hear Chuck say that he loves Blair, but it also shows that he is too hesitant to pursue her and that he may simply not be ready.

Season 2, Episode 24: When Chuck gave Blair the perfect prom

Blair initially believes Chuck sabotages her chances of becoming prom queen because she notices him voting for her rival in the ballot and destroying her corsage. In an unexpected turn of events, Blair is crowned prom queen, and Chuck admits to Serena that he ended up voting for her 150 times, and that when Blair saw him with her competitors’ votes, he was actually taking the votes out. When Serena questioned about the corsage, he simply stated that Blair looked better without it.

Episode 25: When Blair kept fighting for Chuck, even though he gave her every reason not to 

Blair admits to overhearing Chuck’s conversation with Serena and decides to confront him once and for all after he repeatedly makes excuses for his feelings towards her. Blair tells him that she doesn’t want Gossip Girl to be correct in portraying her as weak, and she tells Chuck once more that she’s in love with him and that she wants to hear it finally from him. He tells her there may have been a time when it was true, but it’s now a thing of the past.

Season 2, Episode 25: Chuck confessed that he loved her for the first time (twice!)

Blair is on her way home when she notices Chuck waiting for her outside her lobby door. When she asks what he’s doing there, he says he’s traveled all over Europe collecting her favorite things. She questions why he returned, and he admits that she was right that he was a coward for leaving her again, and that he realized he had to return for her. Blair was understandably hesitant to accept Chuck’s confession, but Chuck swears she can believe him this time and finally admits he loves her as well. She kisses him while asking him to repeat those words, which he does.

Season 3, Episode 2: When their snuggles made everything okay

After the friend circle discovers the difficulties of starting college or adult life after high school, Blair visits Chuck while he is sleeping and lays in bed with him. She asks if he’s OK, and he responds, “I am now.” The episode ends with the two cuddling together!

Season 3, Episode 3: When he shared his plans for the future with her

Blair and Chuck decide to meet outside per Chuck’s request, as he wants to share big news with Blair. He informs her that he intends to purchase The Empire Hotel with all of his shares and all of the money he’s acquired. He says he’s confident he’ll succeed because she believes in him.

Season 3, Episode 12: Chuck confided to Blair

On the anniversary of his father’s death, Chuck recalls Bart’s final moments, regretting not being there for him at the time. Blair comes across him while he is recollecting his memories, and he decides to confide in her that Bart always thought he was weak and couldn’t be there when he died. Blair tells him that he couldn’t handle emotions back then, but he’s a man in ways that his father was not. They get up and walk to the cemetery so Chuck can say his final goodbyes properly.

Season 3, Episode 17: Their heartbreaking breakup

After Chuck loses the Empire State Hotel to Jack, Chuck and Blair are faced with the difficult decision of reacquiring it. Jack suggests Blair do a favor for him in order for him to get it back: sleep with him. Blair decides to do it, but is surprised to learn that Chuck allowed it in the first place in order to reclaim the hotel from Jack. When Blair confronts Chuck, he does not deny her accusation but instead reminds her that she told him she would stay with him through the worst of everything, to which Blair responds that she didn’t realize his worst was to undermine her, resulting in the two breaking up.

Season 3, Episode 22: The Empire State Building failed make-up 

Chuck gives Blair a deadline, telling her that she must meet him at the Empire State Building or he will “close his heart to [her] forever.” Blair is at a crossroads. Chuck arrives with flowers to greet Blair and wait for her at the top. Blair eventually lets her heart take the wheel and starts to follow after Chuck; however, Dorota’s water breaks before she can do so, and Blair and Dan rush her to the hospital. Blair eventually fulfills Dorota’s wish to see Chuck, but he has already left, and the flowers are discovered in the trash. Chuck decides to sleep with Jenny out of rage. Blair discovers this after Dan punches Chuck for sleeping with his sister and argues for him to tell when they finally admit the truth, resulting in Blair and Chuck breaking up.

Season 4, Episode 2: When Chuck wanted to change his identity

After getting shot and nearly killed in the Season 3 finale, Chuck decides to change his ways and adopts the alias Henry. Serena advises against it, telling him that if he continues down this path, he will lose everything he has ever cared about. Chuck tells her that he lost the only thing he cared about anyways and that he will continue with his plans of legally changing his name. Later, Blair re-encounters Chuck, finally feeling a weight lifted off her shoulders, and tells him that she no longer loves him, but her world wouldn’t be hers without him in it.

Season 4, Episode 7: WHEN THEY BROKE their treaty

When Chuck and Blair were constantly at odds, Nate and Serena devised a plan in which they sat down with the two to draft and sign a peace treaty. They explain that if either of them violates the treaty, the other will be kicked out of their friend circle. At the end of the episode, the two started bantering back and forth about their mutual hatred for each other until Chuck tells Blair that their treaty was off before ripping the paper in her face. That moment led to them sharing a passionate, fiery kiss and then having sex on top of her piano.

Season 4, Episode 9: When Chuck admitted he was still in love with Blair

After both Blair and Chuck make a promise that their success is more important and that their relationship is only going to be transactional, Blair is caught off guard during sex when Chuck subtly blurts out that he loves her. The two pretend that moment never happened, but as a viewer, I can’t help but notice it!

Season 4, Episode 9: When their fling Was revealed

Later in the same episode, Blair admits to Chuck that she overheard him say he loved her, and he admits that he truly meant what he said. They agree to accept the consequences of their relationship, only for Jenny to secretly pull back the curtain and reveal them to the crowd downstairs as they kiss. Blair tries to explain what happened to Anne, but Anne reiterates how she told Blair that the board was opposed to her rumored relationship with Chuck. They feel it ruins her image and makes her unfit to run the foundation, causing them to back out of giving her the face of the brand.

Season 4, Episode 22: When Chuck saves Blair from Russell

Russell transports Blair to Chuck’s new hotel site and confines her to a room. Russell traps Blair to get back at Chuck because he realizes Blair is the one person he loves the most. While the interaction is taking place, Blair secretly calls Chuck to let him know what is going on. Russell flicks a lighter around, attempting to burn the room down. Chuck, Raina, and Nate track down the two and apprehend Russell before he causes any harm to anyone, and he is arrested. Blair later claims that she called him because she forgot to dial 911 and he was still on her speed dial. Chuck expresses regret for his actions.

Season 4, Episode 22: When they let each other go

Chuck asks Blair if she truly loves Louis after spending the entire day with him, and Blair says she does, but not as much as she loves Chuck. She explains that her love for Louis makes her happy, whereas her love for Chuck is intense and all-consuming. Chuck ponders her response, and before she can break up with Louis, Chuck intervenes and tells them that they have his blessing and that he is excited for their marriage. Blair finds Chuck and questions him about why he did that. He admits that all he wants is for her to be happy, and that if Louis gives her that, then she should not let that go. They promise to each other that they will always love each other before splitting up.

Season 5, Episode 6:  When Chuck apologizeD to Blair for everything

Chuck swallows his pride and visits Blair to apologize for everything he has done wrong to her, including losing his temper when Blair’s new boo Louis proposed to her, treating her like property, not telling her he loved her even though he knew he did, and finally giving up on their relationship when she never did. Tears are streaming down my face as we speak. 

Season 5, Episode 7: Blair trieD to expose Chuck

Chuck attempts to make a genuine apology to Blair, but she doesn’t buy it and sets out a plan to prove that Chuck is still up to his old tricks. Blair eventually confronts Chuck in a back room. She starts flirting with him and tries to seduce him to see if he will fall into his old patterns. He resists at first, but eventually gives in and kisses her.  Blair slaps Chuck and tells him she knew he was lying about being a different person and that she knows she made the right decision by marrying Louis. Blair is unaware, however, that Chuck did it on purpose in order for Blair to finally let go of him.

Season 5, Episode 10: When Chuck acceptED Blair’s baby as his own

After initially being upset that Blair was pregnant and it wasn’t his child, Chuck eventually comes around and tells Blair that he made a mistake in not making a decision when Blair asked and that just because Louis is the father doesn’t mean Blair has to choose him. Chuck continues by saying that he will love her baby as much as he loves her, and that breaking up her family would have been selfish. 

Season 5, Episode 11: The tragic car accident

Chuck and Blair are involved in a near-fatal car accident, which causes Blair to lose her baby. Chuck is critically injured and on the verge of death as his body continues to reject blood transfusions. Blair, in a desperate attempt, prays to God that Chuck will not die. She promises God that if He lets Chuck live, she will keep her promise to marry Louis. After she’s finished, a nurse arrives to inform her that Chuck is awake and looking for her. She enters his room and tells him that just because they cannot be together doesn’t mean she doesn’t love him.

Season 5, Episode 13: WHEN Chuck crasheD Blair’s royal wedding

Blair is waiting for her wedding to begin when her mother, Eleanor, enters and invites Chuck into the room. Now alone, Chuck begs Blair not to marry Louis and to run away with him right then and there, but Blair refuses. She admits she has always loved Chuck and that her love for him grows every day, but they can’t be together even if she doesn’t belong with Louis and that she is doing everything for Chuck.

Season 5, Episode 14: WHEN Chuck pleaded for Blair to choose him

Blair flees to find Chuck after literally becoming a runaway bride, as the two discuss their lingering feelings for one another. Chuck begs her not to leave with Louis, and he promises to help her get through the situation, whether it’s assisting her if Louis or his mother threaten her, or even paying her dowry at any cost. Blair refuses because she does not want him to buy her freedom and asks him to leave her to handle it. Chuck admits in a heartfelt line that he couldn’t bear the thought of her with anyone else and would do anything to have her with him. Blair does not respond and quietly exits, leaving Chuck puzzled.

Season 5, Episode 17: Chuck pAID for Blair’s dowry

One of the most significant setbacks to Blair’s divorce from Prince Louis was the requirement that she pay a dowry. The dowry was too expensive for her family to afford, so she was forced to stay in the unhappy marriage. Chuck once told Blair that he would pay it for her no matter what, but she refused. We learn from Dan’s argument with Chuck that Chuck has already paid off Blair’s dowry, which irritates Dan because he believes it would bankrupt the Waldorfs.

Season 5, Episode 24: Blair’s declaration of love for Chuck

At a crossroads between her new relationship with Dan and her lingering feelings for Chuck, Blair finally decides to choose Chuck at the end of Season 5 by delivering the most iconic line — I just have to let you read it for yourself: “You’ve fought for me all year. I’ve come to fight for you. You said I always bet against you, but this time I’m all in.” I’m all in for this relationship too!

Season 6, Episode 1: When they confirmed that they are each other’s priorities

Chuck and Blair go on a summer trip to Monte Carlo prior to the events of season 6, but their normal lives resume once they return to New York. Chuck introduces Blair to Amira in an awkward encounter, and Blair introduces Chuck to Jean Pierre. When they are alone, they confirm that they are not in a relationship with the people they introduced each other to, with Chuck using Amira as a weapon against his father and Blair knowing Jean Pierre because he is the head of public relations. The two conclude their conversation by promising to remain committed to each other when the time comes.

Season 6, Episode 3: When Chuck was nothing but a gentleman

Chuck comes to Blair’s aid after a mishap during her fashion show, and Blair expresses her gratitude for his support in preparing for the show. Chuck tells Blair that she deserves to be celebrated and hugs her.

Season 6, Episode 9: That time they shared the best goodbye kiss of all time

Chuck decides to book a flight to Moscow after being threatened by his father Bart (plot twist: He’s alive!) to do so in order to keep Blair and Lily safe. However, before he can board the plane, Blair tries to stop him. He tells Blair that if anything happened to her, he wouldn’t be able to live with himself, and asks for her to wait for him one last time. As a farewell, she asks that he kiss her, and we witness a sweetest and simultaneously heartbreaking kiss scene between the two before he keeps his word and boards the plane.

Season 6, Episode 10: When Chuck proposed to Blair for real

Chuck was advised by Doug to marry Blair in order to obtain spousal privilege and avoid being forced to testify against her husband (in this case, Chuck). Blair accepts the offer without hesitation and Chuck officially gets down on one knee to ask her to marry him.

Season 6, Episode 10: When they said “I do”

While on the run from the cops for his warrant for invasion of privacy and slander, the entire group comes together as Blair and Chuck announce their engagement and their plans to marry that day at the Bethesda Fountain. Dorota assigns Eleanor to retrieve the dress, Nate and Jack to retrieve the rings, Dan to retrieve the flowers, and Georgina to retrieve the cake. The wedding goes ahead as planned, with Cyrus officiating; however, the happy engagement is cut short when the police arrive immediately after they recite their vows and kiss, and end up transporting the newlyweds to the police station.

Season 6, Episode 10: The introduction of their son

We can see the family life of our favorite television couple after a five-year time jump to 2017. Blair is still happily married to Chuck while successfully running her mother’s fashion line. Dorota can be seen helping a small child pick up his toys, and when he turns around and runs after Blair calling her mom, we realize that this is the son of Chuck and Blair, aptly named Henry (I’m curious if this name is related to Chuck’s desire to change his name to Henry in Season 4).

This article was originally published on 9/19/17. It was updated on 4/6/23.

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