Everything about Gossip Girl was dramatic – in particular the relationship between central characters Chuck and Blair. Spanning the show's entire six-season run, their romance was rocky (and admittedly pretty toxic) but addictive for fans to watch unfold through all its highs and lows.
Even when they weren't technically together, Chuck and Blair provided plenty of entertainment. Their chemistry is electric, and the show was often at its best in episodes that focus on their relationship. With so many pivotal moments, there are some episodes that certainly stand out as Chuck and Blair's most important relationship milestones and turning points.
The End Of The Affair? - Season 5, Episode 11
There are multiple dips in Chuck and Blair's relationship, but "The End Of The Affair?" is definitely the saddest. In the fallout of a car accident that ruined their plans to run away together, it sees Blair recovering from losing her baby and dealing with her promise to God that she'd cut Chuck out of her life if he let him survive.
Sure, it's one of the more convoluted Gossip Girl twists. However, the emotional repercussions feel so real. This is the lowest point in their relationship – they were so close to finally being happy, but trauma tore them apart. The stakes are higher than ever, and it seems like there really is no coming back from this.
War At The Roses - Season 4, Episode 8
After hurting each other too many times, Chuck and Blair are tied up in arguments in early season four. They might sign a peace treaty at Nate and Serena's insistence, but the bad blood between the two still threatens to boil over throughout "War At The Roses".
Both have plenty of reasons to hate the other at this point (especially Blair, seeing as how Chuck slept with Jenny) but it's clear from the start that this 'hatred' is actually barely masked sexual tension. Viewers can feel it building for the entire episode before it finally explodes in one of the show's most passionate scenes, perfectly set to Robyn's "Dancing On My Own".
The Return Of The Ring - Season 5, Episode 24
Season five isn't the most successful season for Chuck and Blair, with obstacles such as the car crash, Louis, and Dan all thrown their way. Just when it seems like it'll end without any reconciliation, Gossip Girl leaks pages from Blair's diary revealing her lingering love for Chuck.
Even then, the road isn't easy. When Blair goes to declare her love, Chuck rebukes her. Blair later chases him all the way to Monaco to win him back, declaring that she's "all in". It's a powerful moment for a pair who have jumped in and out of a relationship for five years at this point – finally, they're ready to commit for good.
Seventeen Candles - Season 1, Episode 8
It's tough to remember, but there was a time when Chuck was just Blair's boyfriend's best friend. All that changes when the pair sleep together shortly after Blair and Nate's breakup, with Blair trying to assuage her guilt in "Seventeen Candles".
Until this point, Chuck has been portrayed as nothing more than a morally dubious playboy. However, cracks begin to appear in this facade when he reluctantly admits Blair has given him "butterflies" and turns up at her birthday party with a luxurious gift. He has a long way to come, but it's the beginning of a radical shift for both characters in the long run.
The Wrong Goodbye - Season 4, Episode 22
The season four finale is one of the most heartbreaking for Chuck and Blair fans. After saving Blair from Russell, Chuck takes her for "one drink" that turns into the pair gatecrashing a bat mitzvah and sleeping together. Blair plans to leave Louis so they can be together, but Chuck steps back and gives them his blessing.
It's a major turning point for Chuck. Just one season earlier, he was making all the wrong decisions in their relationship and hurting Blair over and over again. Now, he's the one to make the mature call to give her a shot at a happy life – even if he's not a part of it.
New York, I Love You XOXO - Season 6, Episode 10
As the show's big finale, there was no way "New York, I Love You XOXO" wouldn't tie up the loose ends of Chuck and Blair's relationship. On the run from the police, the pair decide to have Gossip Girl's most impromptu wedding in Central Park – one that's dramatic, scandalous, and so very them.
There's also the show's epilogue, set five years later, that reveals they go on to have an impeccably well-dressed son named Henry. Both are successful, happy, and as in love as ever. After six seasons of angst and drama, this is the happy ending they've always deserved.
Victor/Victrola - Season 1, Episode 7
For Chuck and Blair fans, the show doesn't really get going until episode seven. It's then that Blair – exhausted by his inability to commit – ends her relationship with Nate. She attends the opening of Chuck's burlesque club and throws caution to the wind with a spontaneous striptease.
Chuck is awed by this side to Blair he's never seen before, and the pair later end up having sex in his limo. Even before Chuck and Blair's iconic limo hook-up scene, this episode is full of signs that they'd be compatible. Blair is the one who goes to give Chuck her support before making his business proposal to his father, proving that they already have a strong friendship foundation to build on in the future.
Double Identity - Season 4, Episode 2
New York is as much a character in Gossip Girl as Chuck or Blair, but the season four opener welcomed a new destination: Paris. Determined to put Chuck behind her, Blair has spent the summer shopping her way through the Champs-Élysées, unaware he's actually in recovery from a gunshot wound received while trying to save her engagement ring.
They aren't kept apart for long. The pair cross paths and Blair is forced to convince him to return to Manhattan instead of pursuing a new life in Europe. Their reunion on the train station bridge is one of the most beautiful scenes in the entire show (and features one of Blair's best outfits). It sums up their relationship perfectly: after all the pain he's put her through, Blair admits her world would be easier without Chuck – but it wouldn't be her world without him in it.
The Goodbye Gossip Girl - Season 2, Episode 25
Season two sees Chuck and Blair in a constant tug of war as to who'll say "I love you" first. Both know exactly how the other feels, but it's more a matter of pride than anything else, with Chuck, in particular, struggling to let Blair in for good.
The season finale sees him come so close – only for Gossip Girl to drop the bombshell that Blair slept with his uncle earlier that year. Betrayed, Chuck denies his feelings once again. Thankfully, he comes to his senses to surprise Blair in the episode's final scenes, finally dropping those three little words. It's the grand romantic gesture Blair always wanted, and one of the purest moments of their whole relationship.
O Brother, Where Bart Thou? - Season 2, Episode 13
Chuck's relationship with his father is turbulent, to say the least. Despite always feeling like he wasn't good enough in Bart's eyes, Chuck is left reeling by his (apparent) death in a car crash in season two. He spends the day of his funeral drunk, with Blair chasing after him to pick up the pieces.
In all the chaos, Blair vows to stand by him through everything and finally admits her love. Chuck's in no state to deal with this and cruelly rejects her, only to show up at her house that evening, completely broken. It's the simple, raw moments that make this episode so powerful, and it's the ultimate example of the deep connection Chuck and Blair share, even in their darkest times.
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November 14, 2021 at 08:00AM
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Gossip Girl: 10 Best Chuck & Blair Relationship Episodes - Screen Rant
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