Summary

• Chuck and Blair's relationship in Gossip Girl was filled with drama and toxic moments, but also undeniable chemistry and love.
• The most important relationship milestones and turning points for Chuck and Blair occurred throughout the series, showcasing their growth and feelings for each other.
• Some of the best episodes focused on Chuck and Blair's relationship, highlighting their intense emotions, conflicts, and their strong bond even when they were apart.

Everything about Gossip Girl was dramatic – in particular the relationship between central characters Chuck and Blair - and the best Chuck and Blair episodes showcase that drama very well. 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. Part of the fun of Gossip Girl was seeing these two characters bring out both the best and the worst in one another as they grew up.

Even when they weren't technically together, Chuck and Blair, played by Ed Westwick and Leighton Meester, provided plenty of entertainment. Their chemistry was electric, and the show was often at its best in episodes that focused on their relationship. With so many pivotal moments, some episodes certainly stand out as Chuck and Blair's most important relationship milestones and turning points.

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"Much 'I Do' About Nothing"

Season 1, Episode 18

This season 1 episode is a huge Chuck and Blair episode, though the biggest reveal doesn't come from one of their scenes together. It's a big deal when Chuck tells Nate that he loves Blair. Since Nate and Blair were in a serious relationship that predated the show, and Chuck and Nate were supposed to be best friends, this is a problem for their friendship dynamic.

While Chuck doesn't do anything about his feelings just yet, and it will be years before Chuck and Blair finally commit to one another, this is still one of the most important episodes about the fan-favorite couple. It shows that there were strong feelings between them from the start of the series, even though Chuck would ultimately deny it later.

"It's A Wonderful Lie"

Season 2, Episode 12

There are so many fun Gossip Girl events throughout the show's six seasons, including the Snowflake Ball. Any opportunity for the characters to dress up in fancy, elegant clothing is fun to watch, and these parties often include lots of drama. Some of the most emotional moments in the series happen at those parties, though that's not what happens here. Instead, it's a game of cat and mouse for this Chuck and Blair episode.

In this season 2 episode, Chuck and Blair try to set each other up for the party. They won't admit that they actually have feelings for each other, yet their tension and chemistry are strong. It's made abundantly clear to the audience that they aren't setting one another up to try to make each other happy, but instead to prove that they are the better match, even if they don't want to say it out loud.

"The Grandfather"

Season 2, Episode 19

Blair dates several people throughout the series, although it's hard not to want her to be with Chuck the entire time, given the love that they have for each other from start to finish. In "The Grandfather," Serena and Chuck think that Blair's love interest, Carter, is bad for her, which proves how much Chuck cares about Blair since he actually agrees with Serena for once.

Some of the most compelling Chuck and Blair episodes are before they officially date due to the sparks between them and the snarky banter that they often exchange. "The Grandfather" is one of those episodes. Chuck and Blair spend a lot of the episode at odds while Blair is trying to embrace a wilder lifestyle after her Yale rejection. Chuck just wants to keep her safe, but she won't let him, turning to Nate instead.

"Riding In Town Cars With Boys"

Season 5, Episode 10

In "Riding In Town Cars With Boys," one of the most intense episodes of the whole show, Chuck and Blair take a scary car ride. Blair is pregnant and Chuck gets injured, and for a little while, it's unclear if they will be alright. This terrifying experience bonds the two characters even more, and it allows them to see that they don't want to live without each other. As often happens with horrifying situations, Chuck and Blair begin to think more carefully about who is important to them.

Much of the events of the episode before Blair and Chuck end up in a town car together revolve around each of them getting input from others about their relationship. While Chuck hangs on the words of the press about Blair and Prince Louis' relationship problems, it's Nate who encourages Chuck to talk to Blair. While Blair worries about how her pregnancy is affecting her appearance, Dorota reminds her that she hasn't even seen Louis while he's in New York. The entire episode acts as a reminder that even when Chuck and Blair are apart, they're drawn to one another.

"The Revengers"

Season 6, Episode 9

Season 6 is the best one for Chuck and Blair fans since this is when they finally end up together. Their love story spans the entire run of Gossip Girl and in "The Revengers," Blair realizes that she has to admit her feelings as she's scared of losing Chuck. After watching so many seasons with the characters dancing around their love and listening to their pride more than their hearts, this is a satisfying and sweet episode.

The events of "The Revengers" see Blair team up with Serena, Georgina, Sage, and Ivy to finally take down Chuck's father. Chuck's father, of course, attempts to have him killed during the episode, terrifying Blair further. Blair and Chuck end up being the ones to witness Bart falling off the side of a building when he tries to hurt Chuck, which only bonds them to one another even more as well.

"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 the saddest, yet still one of the best Chuck and Blair episodes. The fallout of a car accident that ruined their plans to run away together 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.

It's one of the more convoluted Gossip Girl twists but 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 have some of the worst Gossip Girl fights in early season 4. 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" and the emotional storyline makes for one of the best Chuck and Blair episodes.

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 5 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 one of the best early Chuck and Blair episodes, "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 4 finale is one of the most heartbreaking for Chuck and Blair fans. After saving Blair from Russell, Chuck takes her for "one drink" which turns into the pair gatecrashing a bat mitzvah and sleeping together. Blair plans to leave Louis so that they can be together, but Chuck steps back and gives them his blessing.

It's a major turning point for Chuck as 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, which is why it's one of the best Chuck and Blair episodes of the series.

"Victor/Victrola"

Season 1, Episode 7

For Chuck and Blair fans, the show doesn't get going until episode seven. That's because "Victor/Victorla" is where Chuck and Blair first get together. 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 of Blair he's never seen before, and the pair later end up having sex in his limo. Even before Chuck and Blair's limo hook-up scene, which is one of the most iconic Gossip Girl couple scenes, 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 4 opener welcomed a new destination: Paris. Determined to put Chuck behind her, Blair spent the summer shopping her way through the Champs-Élysées, unaware he was 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 Gossip Girl (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 2 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 2 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 gesture Blair always wanted, one of the most romantic Gossip Girl moments, 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 2. 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. Despite how sad the episode is overall, its emotional depth makes it the best Chuck and Blair episode of Gossip Girl.