Chuck (Ed Westwick) and Blair (Leighton Meester). Blair and Chuck. They are, perhaps, the most beloved romance in all of Gossip Girl history. With Season 6 possibly wrapping up their love/hate love story (whether it'll be with a pretty bow is yet to be determined), we take a look back over every fate-driven moment of Chair’s complex love story.
Season 1
The limo
Where it all began. For two such classy people, gettin’ it on in the backseat is pretty out of character — even if it is the backseat of a limo. But Chuck always brings out Blair’s wild side, which is why they’re so good together.
The necklace
Both Chuck and Blair are too intent on ruling the world to admit how much their hookup means — but Chuck says it the Upper East Side way: with a mad-expensive present and about half an hour of neck-stroking. Blair is still fixated on Nate, and Chuck is still fixated on never loving anyone ever, but it’s clear their feelings are too strong to ignore.
The helipad
Of course, it would never be that easy. Even with Nate out of the picture, Chuck and Blair can’t stop getting in their own way. Instead of whisking Blair off to Europe for a romantic summer together, commitment-phobe Chuck leaves her waiting for him alone at the helipad. Man, we hate when guys stand us up at the helipad.
Season 2
The power struggle
If Chuck thinks Blair will crawl back after his abandonment, lonely and forlorn, he’s dead wrong: Queen B comes roaring back from Europe with an aristocratic boyfriend in tow. Chuck is more besotted than ever, but neither he nor Blair can bring themselves to be the first to admit that they’re in love. The battle to force each other to say those infamous three words, eight letters becomes a game in itself — one they aren’t sure they can leave behind for a chance at a real relationship.
The loss
But, as usually happens, real life intervenes to put their petty games in perspective. When Chuck’s father dies, Blair swoops in to comfort him, admitting what he’d known all along: That she’s in love with him. Unfortunately for her, Chuck is the kind of guy who reacts to strong emotion by flying off to Thailand for an orgy.
The reunion
Finally. Finally. After months of brooding Chuck gets it together, admits that he loves Blair, and wins her back the only way he knows how: With lots of expensive presents from all over Europe.
Season 3
The honeymoon
Chuck and Blair are finally together, and they can express their love with manipulative sex games, team scheming, and lots of lounging around the penthouse in various states of undress...
The betrayal
… until he tries to trade her to his slimy uncle for a hotel. Blair can appreciate a good scheme, but not when she’s the victim.
The Humphrey
Hey, Chuck, here’s a suggestion for how to win Blair back after you’ve tried to trade her for a hotel: Don’t sleep with Jenny Humphrey (Taylor Momsen). The look Blair gives him when she finds out probably hurts worse than the gunshot wound he gets a few days later.
Season 4
The Prince
Ol’ Chuckles has a bit of a quarterlife crisis, reinventing himself as a simple barback named Henry Prince to win the heart of sweet Parisian peasant Eva. But his billions soon beckon, and though he tries to bring Eva with him, ultimately she can’t hack it in his world — especially with Blair determined to take her down.
The feminist awakening
Post-Eva, what’s keeping them apart? Only B’s sudden realization that if things keep going as
The rejection
Blair tells Chuck that she’s ready to begin their wheeling-and-dealing life together, but in true Basshole form, he effs it all up by intentionally humiliating Dan.
Then Blair dumps him. Again.
The Hora
Blair gets busy planning a new life with Prince Louis of Monaco (Hugo Becker), which prompts some scary downward-spiral moments from Chuck. Still, even the promise of a perfect fairy tale ending isn’t enough to keep Blair away from her dark prince.
After sharing a giddy dance at a random Bar Mitzvah, Chuck and Blair end up doing it in a coat closet. Give it up, kids. If being thrown around in chairs during a religious ceremony gets you in the mood, you might as well admit you’re never going to quit each other.
Season 5
The little crash
Chuck and Blair spend most of the beginning of this season avoiding each other — actually, quite a mature decision, given that Blair’s preggo with another man’s child. But that doesn’t mean they’re not on each other’s minds. In fact, Chuck basically plunges himself into a dangerous motorcycle crash just to get over her. It doesn’t work. So remember that, kids: Crashing your motorcycle never helps.
The masks come off
Blair becomes obsessed with the idea that Chuck’s still pursuing her. From where we’re standing, it looks like the opposite — Blair can’t stop goading him to try to get her back. Things come to a head at Sleep No More, when Blair corners him and shows him her neck, which — he finds irresistible? These two are weird.
When Chuck kisses her, she claims it’s proof he’s still a scoundrel and runs back to Louis, and he claims that was his intent all along. But if you ask us, that kiss was the only honest moment between them this season.
The reunion
Thanks to an amazingly selfless Dan, Chuck and Blair finally admit what everyone knows: they’re still in love and they’re never going to be able to stay away from each other. But their happiness is short-lived, because here comes...
The big crash
As they prepare to run off together, their limo crashes. Chuck is unconscious and Blair loses her baby. Blair, devastated, makes a promise to God that if he allows Chuck to live, then she will
walk away from their love. He lives but is kept in the dark about why she can't be with him. Her internal conflict is a secret to everyone except Dan, which only serves to bring them closer together. And then comes...
Dair
After her marriage to Louis reveals itself to be the worst decision ever, Leighton attempts to get out of it. Dan continues to be her rock and eventually she discovers that her heart is no longer with Chuck... it's with Dan! And after Louis grants her the divorce, she and Dan are free to be together. So is this the beginning of the end of the Chair love story? We have a feeling it's not. But only time will tell!
