1. Prom Queen Ballot (S02E24)
The best 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 an 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. 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 afterward would be the first intimate moment that we see between the two that changed everything
3. 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!”
4. 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 than “Chair” fans wanted from the couple more than lifelong happiness and with Henry by their side, they are sure to find that.
5. 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.