This is the episode right after Chuck discovers the crushing revelation that Blair is pregnant with Louis’ child. It’s this discovery that finally awakens him from the bubble of self-destructive lack of emotion that he put himself into in order to cope with the pain of his breakup with Blair and everything that followed. Still, when Chuck and Blair run into each other on the street the next day, they fall back into talking like they always do. Chuck literally stops her in the street to seriously ask if she’s okay. Even though he was shaken by the news, he’s more concerned about Blair’s well-being. How she is and whether she’s okay is always what’s most important to him. I think that’s a big theme for them throughout the series. Even when they’re not together or they’re at their lows, they’re always there for each other and concerned about one another. There’s also an ease to their relationship that shows how comfortable they are with each other. I love this little scene because it demonstrates the support and comfort they always find in each other, whether they’re together or not.