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Chuck Bass and Blair Waldorf are one of TV’s most-loved couples. They went from being enemies to lovers and back and forth for all six seasons of the hit show and brought viewers on every different kind of trip possible between all of the breakups, schemes, tender moments and more. This is a list of the 10 Best Moments of the couple.

1. Prom Queen Ballot (S02E24)

Probably the sweetest moment of this series came when Blair won Prom Queen against all of the odds and sabotages of her minions. Although Chuck had already perfected Blair’s outfit and entire day prior leading up to the dance (keeping in line with Blair’s scrapbook), he took it one step further by placing in 150 votes ‘for’ Blair and taking out Nelly Yuki’s votes to secure the crown for Blair. Even though it initially went unnoticed by Blair herself, Serena and Dan both found out what Chuck had done and called it as it was: sweet. Something Chuck Bass isn’t exactly known for being.

2. Chuck on Rooftop (S02E14)

After Bart Bass’ death, Chuck disappears and is eventually found in Bangkok by his loving Uncle Jack. After continuous drinking and a party at Victrola, Chuck finds himself on the rooftop mere inches away from a drunken fall to his death. Blair knows exactly where to find him and helps talk him off of the ledge by explaining how much he means to her, “whatever you want to do to yourself, please don’t do that to me!”

3. Strip Tease (S01E07)

Soon after explaining to Blair his intentions of purchasing a burlesque club, Chuck finds Blair in Victrola after her break-up with Nate. Blair is more interested in showing off her feelings than talking about them and goes up on stage after being dared by Chuck. Not only does she do her thing but she was impressive at it as well! Chuck was attentive the entire time and this moment marked the beginning of the Chuck and Blair era that we know and love.

4. Limo Scene (S01E07)

After leaving the club, Chuck and Blair head home in Chuck’s limo. Blair is newly-single and feeling great after letting her inhibitions go at the club and a short makeout session eventually leads to Blair losing her virginity to Chuck in the limo. What was at the time a secret that Blair kept deeply hidden afterwards would be the first intimate moment that we see between the two that changed everything.

5. White Party (S02E01)

The White Party gave us all a very monumental line that would repeat itself throughout the second season of Gossip Girl. Although Blair attended the party with Lord Marcus, she was willing to end the night with Chuck by delivering this kicker: “eight letters, three words, say them and I’m yours.” Unfortunately, Chuck could not say them just yet. That does not change the iconic nature of the end of that episode, though!

6. “I love you” (S02E25)

When Chuck was finally able to say those three words, man, was it a special time. The last episode of Season Two brought us this great moment between Chuck and Blair. Blair explained how consuming her love for Chuck was and for the first time, Chuck was able to say it back. He gave Blair gifts from his different stops in Europe that he had just traveled through and explains that although he was not planning to buy her the different things, he saw her everywhere that he went and knew that he had to.

7. The scheming

Chuck and Blair together are the most dynamic duo that you can find on television. They’re equal parts conniving and manipulative and so similar while being so perfectly like-minded and compatible. From teaming up to take down Georgina Sparks to helping save Chuck’s business from Jack Bass, when these two got together we knew that whatever task was at hand was going to get done. Typically, followed by a reconciling of the couple or one of their many breakups.

8. Empire State Building (S03E22)

Potentially one of the most iconic meet-ups in the show, the Empire State Building situation was equally heartwarming and heartbreaking. At the beginning of the twenty-second episode of Season Three, Blair was afraid of being hurt and it was getting in the way of her being able to be with Chuck. Aside from those feelings, Chuck told her to meet him at the top of the Empire State Building at 7:01 if she wanted to be with him. Blair eventually made the decision to meet him but as she was leaving to do so, Dorota went into labor causing Blair to miss her meeting time. Chuck was prepared with Blair’s favorite flowers and an engagement ring that would eventually be stolen by muggers who would shoot Chuck. Their feelings were in the right place just not at the right time, as usual.

9. Wedding (S05E13)

At Louis and Blair’s wedding, Chuck tries his hardest to sway Blair away from marrying Prince Louis. Blair professes her love to him but is not willing to cancel the wedding. Georgina Sparks does her magic and ruins the loving nature of the wedding and of Blair and Louis’ marriage.

10. Little Chuck (S06E10)

Potentially the best thing to come from the series finale of Gossip Girl was not finding out Gossip Girl’s identity or even learning who and who get married. The happiest part was seeing the adorable Henry Bass. It wrapped up the tumultuous story that was Chuck and Blair’s romance and showed that even the hardest of hearts can be softened and happiness can be found! There is nothing more that “Chair” fans wanted from the couple more than lifelong happiness and with Henry by their side, they are sure to find that.

(written by: Bailey Munson)

Written by Bailey

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