1. Burlesque club: (S 01 E 07)
What goes down at Chuck's Burlesque club, Victrola, is the first iconic Chuck and Blair scene that is often referenced throughout the show and the beginning of their intensely complex love story.
2. Chuck rigs prom: (S 02 E 24)
After spending time "sabotaging" Blair's prom plans, we find out that Chuck is actually trying his best to give her the perfect prom night she dreamed of since she was a little girl, including winning prom queen.
Dan: "Who even voted for her?"
Chuck: "Me...150 times."
3. Chuck finally tells Blair he loves her: (S 02 E 25)
The moment we all waited for finally came when we found out that Chuck was in Europe buying some of Blair's favorite things to come back and surprise her with many gifts and a long awaited "I love you, too".
4. Blair comforts Chuck at the hospital: (S 03 E 12)
Due to Serena's unfortunate accident (and relationship) with Tripp van der Bilt, she ends up in the hospital which reminds Chuck of when Bart dies. To comfort Chuck, Blair reminds him that he is becoming a man like his father never was, and to say goodbye once and for all.
5. Chuck gets Blair into Columbia: (S 03 E 20)
After terrible year at non-ivy league NYU, being traded for a hotel, and other random things that us normal people do not go through, Blair just wanted to start fresh and leave her old life. She was able to do this when Chuck finally got things right (after a long time) and helped her get into Columbia by secretly submitting an application for her.
6. Paris train station: (S 04 E 02)
By this point, Chuck and Blair have gone through hell and back and are on the road to recovery on their own. After a summer of going AWOL, Chuck decides to leave his identity behind and live a simple life away from the toxic nature of the Upper East Side. Blair catches Chuck before he leaves to tell him that even though he has hurt her, her world wouldn't be the same without him, and not to be a coward by running away.
7. Bah Mitzvah: (S 04 E 22)
At this point, Blair is supposed to be committed to Louie but cannot deny her love for Chuck. So, after a forbidden tryst between the iconic duo, Blair decides to end things with Louie but is then stopped by Chuck because he believes that the happiness Blair needs can only be found if she is with Louie.
8. "I'm all in.": (S 05 E 24)
As a last ditch effort to secure her future with the right man, Blair chooses Chuck over Dan (thank God), and it leads to disappointment as Chuck refuses her. Fortunately, Blair fights for the relationship and meets up with Chuck due to a tip-off from Uncle Jack.
Blair: "You said I always bet against you, but this time I'm all in."
9. Chuck proposes to Blair: (S 06 E 10)
Chuck and Blair became our generation's (fictitious) Bonnie and Clyde when they escape from the police after Bart's untimely death. Jack finds them hiding away at a bed and breakfast and suggests they get married to avoid Blair being a witness to the crime. Jack: "It's twisted, but it's very you."
Chuck: "Blair Cornelia Waldorf, will you marry me?"
10. Chuck and Blair get married: (S 06 E 10)
Chuck and Blair are so above a courthouse wedding, and thankfully they thought so too because it lead to one of the most beautiful scenes in the whole show.
11. Henry Bass: (S 06 E 10)
Chuck and Blair's son, Henry, melted everyone's hearts and made us feel that all the troubles of their relationship were definitely a thing of the past. It was truly the perfect way to wrap up a six-season romance.
