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''The Goodbye Gossip Girl'' season 2, episode 25
Most satisfying-joyful moment: Chuck finally says ''I love you''
With two seasons of will-they-or-won't-they teasers, Chuck finally came through. After traveling Europe just to pick up some of Blair's favorite things, he gave her the present she'd really been waiting for: three words, eight letters.
Chuck: ''I love you too.''
Blair: ''Like, can you say it twice? No I'm serious, say it twice.''
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''O Brother, Where Bart Thou?'' season 2, episode 13
Most heart-wrenching moment: After Bart's death, Blair tells Chuck she loves him and he leaves her
Despite his inability to commit, seeing Chuck so distraught after Bart's death pulled at every one of B.'s tiny heart strings, invoking the most loving and maternal sides of her. Chuck rejected her, which broke our hearts once, but then came back to her in the middle of the night, only to disappear to Thailand by morning.
Blair: ''But I am me, and you're you, we're Chuck and Blair, Blair and Chuck, the worst thing you've ever done, the darkest thought you ever had, I will stand by you through anything... because I love you.''
Chuck: ''Well that?s too bad.''
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''Victor/Victrola'' season 1, episode 7
Hottest limo ride: Chuck and Blair?s first night together
After her breakup with Nate, Blair lets it all hang out at Victrola, the nightclub Chuck recently opened. The emergence of this new Blair led to a racy romp in the backseat of Chuck's limo — a night the two would always remember.
Blair: ''You know, I got moves.''
Chuck: ''Really? Then why don?t you get up there?''
Blair: ''I?m just saying... I got moves.''
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''Much 'I Do' About Nothing'' season 1, episode 18
Most surprising moment: Chuck and Blair kiss at Bart and Lily's wedding
After Blair inspires Chuck's impromptu heartfelt best man speech, the two share a dance — and a kiss — beginning their short-lived summer romance.
Blair: ''Chuck Bass is a romantic? Who knew?'
Chuck: ''Well, now you do now. That?s all that matters.''
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''The Debarted'' season 3, episode 12
Most heartwarming moment: Chuck opens up to Blair about his father
When the anniversary of his father's death arrived, Chuck was tormented by guilt. Finally able to see Blair as his rock, he confided in her and the two shared a sweet moment in the hospital halls. His gentle kiss her on the head as they walked out arm in arm was more loving than anything the two had ever shared.
Blair: ''I don't think you ran away because you couldn't handle death, I think it's because you couldn't handle feelings. But you're not like that anymore, you're strong, you carry people, you carry me. You're becoming a man in a way that your father never was.''
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''The Return of the Ring'' season 5, episode 24
Best casino-set gambling metaphor: Blair is ''all-in'' for Chuck
Setting up the final season, Blair made the ultimate overture for her one and only. Though Chuck met her declaration of love with an open-to-interpretation silence that would haunt fans throughout the summer, if we were betting types, we'd wager there will be plenty of Chair action set for the back 10.
Blair: ''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.''
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''Enough About Eve'' season 3, episode 6
Most comical scheme: Getting the NYU rep to kiss Chuck
Just because she?s in college doesn?t mean she?s too old for some good old fashioned blackmail. Blair enlisted Chuck to help her snag freshmen toast honors. But it turned out that Chuck unknowingly acted as bait to Mr. Ellis and received a kiss on the lips in exchange for Blair?s prize. Although he was annoyed B had duped him as well, Chuck knew it was just Blair being Blair.
Blair: ''Love me?''
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''The Wrath of Con'' season 2, episode 23
Most frustrating moment: Chuck tells Blair ''it's just a game''
Demanding resolution, Blair put everything on the line for Chuck, inviting him to finally tell her how he felt or endure losing her forever. Cowardly Chuck refused to admit his true feelings.
Blair: ''Then look down deep into the soul I know you have, and tell me if what you feel for me is real, or if it's just a game. If it's real, we'll figure it out, all of us, but if it's not then please, Chuck, just let me go.''
Chuck: ''It's just a game. I hate to lose, you're free to go.''
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''Riding In Town Cars With Boys'' season 5, episode 10
Best reconciliation: Blair and Chuck on the Dan setup
Chuck manned up and pledged himself to Blair and her baby and got her to agree to leave Louis.
Chuck: ''Just because Louis is the father of your baby doesn't mean you should be with him. You should be with me.''
Chuck; ''Because I'm going to love your baby as much as I love you.''
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''The Dark Night'' season 2, episode 3
Most scandalous moment: Blackout make out
Because he left her waiting all summer, Blair attempted to feign disgust at Chuck?s offer to revisit their past ''just once.'' However, Blair's delivery was about as believable as Chuck?s modest request. True desires were revealed during the blackout, as Chuck pretended to be Blair's British boyfriend Marcus (who knew all Brits sounded alike? And yes, that's Ed Westwick's real accent!).
Chuck: ''Just once, that?s all I need.''
Blair: ''You?re disgusting...and I hate you.''
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''Valley Girls'' season 2, episode 24
Sweetest gesture: Chuck helps Blair win Prom Queen
Knowing that what matters most to Blair is utter domination of those around her (regardless of whether or not there is a precedent for prom at Constance), Chuck voted for his beloved 150 times just to make sure she'd win the title of Prom Queen.
Blair: ''I OWN prom!''
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''Inglorious Bassterds'' season 3, episode 17
Biggest OMG did that just happen moment: Chuck and Blair BREAK UP
They've been through a lot together, but even this scheme was too much for Chuck and Blair to handle. Using Blair as collateral to get the Empire Hotel back from Jack, along with her own willingness to be used as such, made Blair realize how twisted the two of them had become together.
Chuck: ''The worst thing I ever did, the darkest thought I ever had, you said you would stand by me through anything. This Blair, is anything.''
Blair: ''I never thought the worst thing you would ever do would be to me.''
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''Double Identity'' season 4, episode 2
Most cinematic setup: Chuck and Blair reunite after Chuck's accident
A train station, a gorgeous gown, and an earnest Chuck Bass. Perfection.
Chuck: ''Your world would be easier if I didn't come back.''
Blair: ''That's true. But it wouldn't be my world without you in it.''
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''The Big Sleep No More'' season 5, episode 7
Best pounce: Chuck and Blair at the masked ball
Blair knew what she was doing cornering Chuck alone and tempting him. She wasn't buying his reformed act. And sure enough, given half the chance, he went in for the kiss. And she went back to plans to marry Louis. Without any clue that Chuck did it for her.
Blair: ''I knew you were the same Chuck. You thought that by one fake apology and a couple of charitable acts you could get me to question all the reasons I'm with Louis. But I was right. You are incapable of change.''
Chuck: ''Seems like you know me too well.''